Updated on 2024/11/01

写真a

 
Takahashi Kyoko
 
Affiliation
Faculty of Medicine, Department of Chemistry, Associate Professor
Title
Associate Professor
External link

Degree

  • 博士（薬学） ( Kyoritsu University of Pharmacy )

Research Areas

  • Life Science / Pharmaceutical chemistry and drug development sciences

Education

  • Kyoritsu University of Pharmacy   Faculty of Pharmaceutical Science

    1986.3

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Professional Memberships

Papers

  • Fullerene derivatives as inhibitors of the SARS-CoV-2 main protease

    Daiki Katagishi, Daisuke Yasuda, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino, Tomoyuki Ohe

    Bioorganic & Medicinal Chemistry Letters   80   129121 - 129121   2023.1

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    Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

    DOI： 10.1016/j.bmcl.2022.129121

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  • Synthesis and evaluation of tofacitinib analogs designed to mitigate metabolic activation

    Yasuhiro Tateishi, Chikako Shibazaki, Kyoko Takahashi, Shigeo Nakamura, Yasuhiro Kazuki, Tadahiko Mashino, Tomoyuki Ohe

    Drug Metabolism and Pharmacokinetics   43   100439 - 100439   2022.4

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    Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

    DOI： 10.1016/j.dmpk.2021.100439

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  • ビスピリジニウム型フラーレン誘導体によるBCR-ABL陽性K562細胞のアポトーシス誘導機構の解析

    鷲見 和也, 多胡 憲治, 中澤 洋介, 高橋 恭子, 大江 知之, 増野 匡彦, 多胡 めぐみ

    日本薬学会年会要旨集   142年会   28S - am01S   2022.3

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    Language：Japanese   Publisher：(公社)日本薬学会  

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  • A bis-pyridinium fullerene derivative induces apoptosis through the generation of ROS in BCR-ABL-positive leukemia cells. International journal

    Kazuya Sumi, Kenji Tago, Yosuke Nakazawa, Kyoko Takahashi, Tomoyuki Ohe, Tadahiko Mashino, Megumi Funakoshi-Tago

    European journal of pharmacology   916   174714 - 174714   2022.2

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    A fusion protein, Breakpoint cluster region-Abelson (BCR-ABL) is responsible for the development of chronic myeloid leukemia (CML) and acute lymphocytic leukemia (ALL). Inhibitors against BCR-ABL are effective for the treatment of leukemia; however, a gatekeeper mutation (T315I) in BCR-ABL results in resistance to these inhibitors, which markedly impedes their efficacy. We herein demonstrated that a bis-pyridinium fullerene derivative (BPF) significantly induced apoptosis in human CML-derived K562 cells and ALL-derived SUP-B15 cells via the generation of reactive oxygen species (ROS). BPF reduced the expression of Bcr-Abl mRNA by inhibiting expression of c-Myc through ROS production. BPF also accelerated protein degradation of BCR-ABL through ROS production. Furthermore, BPF down-regulated the expression of not only BCR-ABL but also T315I-mutated BCR-ABL in ROS-dependent manner. As a result, BPF effectively induced apoptosis in transformed Ba/F3 cells expressing both BCR-ABL and T315I-mutated BCR-ABL. Collectively, these results indicate the potential of BPF as an effective leukemia drug that overcomes resistance to BCR-ABL inhibitors.

    DOI： 10.1016/j.ejphar.2021.174714

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  • Novel Mechanism by a Bis-Pyridinium Fullerene Derivative to Induce Apoptosis by Enhancing the MEK-ERK Pathway in a Reactive Oxygen Species-Independent Manner in BCR-ABL-Positive Chronic Myeloid Leukemia-Derived K562 Cells. International journal

    Kazuya Sumi, Kenji Tago, Yosuke Nakazawa, Kyoko Takahashi, Tomoyuki Ohe, Tadahiko Mashino, Megumi Funakoshi-Tago

    International journal of molecular sciences   23 ( 2 )   749   2022.1

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    Language：English   Publishing type：Research paper (scientific journal)  

    In the treatment of breakpoint cluster region-Abelson (BCR-ABL)-positive chronic myeloid leukemia (CML) using BCR-ABL inhibitors, the appearance of a gatekeeper mutation (T315I) in BCR-ABL is a serious issue. Therefore, the development of novel drugs that overcome acquired resistance to BCR-ABL inhibitors by CML cells is required. We previously demonstrated that a bis-pyridinium fullerene derivative (BPF) induced apoptosis in human chronic myeloid leukemia (CML)-derived K562 cells partially through the generation of reactive oxygen species (ROS). We herein show that BPF enhanced the activation of the mitogen-activated protein kinase/extracellular signal-regulated kinase kinase-extracellular signal-regulated kinase (MEK-ERK) pathway in a ROS-independent manner. BPF-induced apoptosis was attenuated by trametinib, suggesting the functional involvement of the MEK-ERK pathway in apoptosis in K562 cells. In addition, the constitutive activation of the MEK-ERK pathway by the enforced expression of the BRAFV600E mutant significantly increased the sensitivity of K562 cells to BPF. These results confirmed for the first time that BPF induces apoptosis in K562 cells through dual pathways-ROS production and the activation of the MEK-ERK pathway. Furthermore, BPF induced cell death in transformed Ba/F3 cells expressing not only BCR-ABL but also T315I mutant through the activation of the MEK-ERK pathway. These results indicate that BPF is as an effective CML drug that overcomes resistance to BCR-ABL inhibitors.

    DOI： 10.3390/ijms23020749

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  • Development of p62-Keap1 protein–protein interaction inhibitors as doxorubicin-sensitizers against non-small cell lung cancer

    Daisuke Yasuda, Ippei Yoshida, Riyo Imamura, Daiki Katagishi, Kyoko Takahashi, Hirotatsu Kojima, Takayoshi Okabe, Yoshinobu Ichimura, Masaaki Komatsu, Tadahiko Mashino, Tomoyuki Ohe

    Results in Chemistry   4   2022.1

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    Aberrant hyperactivation of nuclear factor erythroid 2-related factor 2 (Nrf2) has been reported in non-small cell lung cancer through overexpression of the p62/sequestosome1 protein, resulting in the acquisition of malignancy and drug resistance. We previously discovered compounds termed K67 and KOA153 that overcome chemotherapy resistance in human hepatocellular carcinoma cell lines by inhibiting the protein–protein interactions between p62 and Kelch-like ECH-associated protein 1 (Keap1), an Nrf2 suppressor. Herein, we synthesized analogs of K67 and KOA153 and investigated their potential as doxorubicin sensitizers against a human non-small cell lung cancer A549 cell line that is addicted to Nrf2 via overexpression of p62. KOA153 and the newly synthesized amide compounds exhibited significant doxorubicin-sensitizing activity without cytotoxicity. In addition, dimethylamide derivatives activated Nrf2 in HEK293 cells expressing normal levels of p62. Therefore, dimethylamide derivatives are likely novel type of anticancer agents.

    DOI： 10.1016/j.rechem.2022.100609

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  • Development of a Fluorescent-Labeled Trapping Reagent to Detect Reactive Acyl Glucuronides

    Chikako Shibazaki, Okishi Mashita, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino, Tomoyuki Ohe

    Chemical Research in Toxicology   34 ( 11 )   2343 - 2352   2021.11

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    Acyl glucuronides are common metabolites of carboxylic acid-containing compounds. Since acyl glucuronides sometimes show high reactivity, they are considered to be involved in drug toxicity. Therefore, it is important to evaluate the risk posed by acyl glucuronides in the development of safe drugs; however, there are no suitable evaluation methods for the early stages of drug discovery. We aimed to develop a trapping reagent that detects reactive acyl glucuronides to assess their risk. We designed a diamine-structured trapping reagent, Dap-Dan, and compared its trapping ability with the reported one that has an amino group, and results showed that Dap-Dan showed higher accuracy. In the trapping assay with 17 medicines containing a carboxylic acid, Dap-Dan trapped acyl glucuronides that had a higher risk of toxicity. In conclusion, Dap-Dan can be useful for evaluating the risk of reactive acyl glucuronides.

    DOI： 10.1021/acs.chemrestox.1c00236

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  • The indole-hydantoin derivative exhibits anti-inflammatory activity by preventing the transactivation of NF-κB through the inhibition of NF-κB p65 phosphorylation at Ser276. International journal

    Xin Lin, Kenji Tago, Nozomi Okazaki, Takanori So, Kyoko Takahashi, Tadahiko Mashino, Hiroomi Tamura, Megumi Funakoshi-Tago

    International immunopharmacology   100   108092 - 108092   2021.11

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    Indole- and hydantoin-based derivatives both exhibit anti-inflammatory activity, suggesting that the structures of indole and hydantoin are functional for this activity. In the present study, we synthesized two types of indole-hydantoin derivatives, IH-1 (5-(1H-indole-3-ylmethylene) imidazolidine-2,4-dione) and IH-2 (5-(1H-indole-3-ylmethyl) imidazolidine-2,4-dione) and examined their effects on LPS-induced inflammatory responses in murine macrophage-like RAW264.7 cells. LPS-induced inflammatory responses were not affected by indole, hydantoin, or IH-2. In contrast, IH-1 significantly inhibited the LPS-induced production of nitric oxide (NO) and secretion of CCL2 and CXCL1 by suppressing the mRNA expression of inducible NO synthase (iNOS), CCL2, and CXCL1. IH-1 markedly inhibited the LPS-induced activation of NF-κB without affecting the degradation of IκBα or nuclear translocation of NF-κB. IH-1 markedly attenuated the transcriptional activity of NF-κB by suppressing the LPS-induced phosphorylation of the NF-κB p65 subunit at Ser276. Furthermore, IH-1 prevented the LPS-induced interaction of NF-κB p65 subunit with a transcriptional coactivator, cAMP response element-binding protein (CBP). Collectively, these results revealed the potential of the novel indole-hydantoin derivative, IH-1 as an anti-inflammatory drug.

    DOI： 10.1016/j.intimp.2021.108092

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  • Novel pyridinium-type fullerene derivatives as multitargeting inhibitors of HIV-1 reverse transcriptase, HIV-1 protease, and HCV NS5B polymerase International journal

    Toi Kobayashi, Takumi Yasuno, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino, Tomoyuki Ohe

    Bioorganic & Medicinal Chemistry Letters   49   128267 - 128267   2021.10

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    In the present study, we newly synthesized four types of novel fullerene derivatives: pyridinium/ethyl ester-type derivatives 3b-3l, pyridinium/carboxylic acid-type derivatives 4a, 4e, 4f, pyridinium/amide-type derivative 5a, and pyridinium/2-morpholinone-type derivative 6a. Among the assessed compounds, cis-3c, cis-3d, trans-3e, trans-3h, cis-3l, cis-4e, cis-4f, trans-4f, and cis-5a were found to inhibit HIV-1 reverse transcriptase (HIV-RT), HIV-1 protease (HIV-PR), and HCV NS5B polymerase (HCV NS5B), with IC50 values observed in the micromolar range. Cellular uptake of pyridinium/ethyl ester-type derivatives was higher than that of corresponding pyridinium/carboxylic acid-type derivatives and pyridinium/amide-type derivatives. This result might indicate that pyridinium/ethyl ester-type derivatives are expected to be lead compounds for multitargeting drugs to treat HIV/HCV coinfection.

    DOI： 10.1016/j.bmcl.2021.128267

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  • Development of fluorescent-labeled trapping reagents based on cysteine to detect soft and hard electrophilic reactive metabolites

    Chikako Shibazaki, Tomoyuki Ohe, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    Drug Metabolism and Pharmacokinetics   39   100386 - 100386   2021.8

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    Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

    DOI： 10.1016/j.dmpk.2021.100386

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  • Substrate recognition of renally eliminated angiotensin II receptor blockers by organic anion transporter 4

    Noguchi, S., Okochi, M., Atsuta, H., Kimura, R., Fukumoto, A., Takahashi, K., Nishimura, T., Tomi, M.

    Drug Metabolism and Pharmacokinetics   36   2021

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    Publishing type：Research paper (scientific journal)  

    DOI： 10.1016/j.dmpk.2020.10.002

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  • Development of Novel Diclofenac Analogs Designed to Avoid Metabolic Activation and Hepatocyte Toxicity

    Yasuhiro Tateishi, Tomoyuki Ohe, Mai Ogawa, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    ACS Omega   5 ( 50 )   32608 - 32616   2020.12

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    Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

    DOI： 10.1021/acsomega.0c04942

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  • Synthesis and evaluation of nevirapine analogs to study the metabolic activation of nevirapine

    Tateishi Y, Ohe T, Yasuda D, Takahashi K, Nakamura S, Kazuki Y, Mashino T

    Drug Metabolism and Pharmacokinetics   35 ( 2 )   238 - 243   2020.4

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    Publishing type：Research paper (scientific journal)   Publisher：Drug Metabolism and Pharmacokinetics  

    © 2020 The Japanese Society for the Study of Xenobiotics Nevirapine (NVP) is widely used as a non-nucleoside reverse transcriptase inhibitor of HIV-1, however, it is associated with severe skin and liver injury. The mechanisms of these adverse reactions are not yet clear, but the metabolic activation of NVP is thought to be related to the injury process. Until now, several metabolic activation pathways of NVP have been reported. In this study, in order to identify the reactive metabolite of NVP mainly responsible for CYP inhibition and liver injury, we synthesized five NVP analogs designed to avoid the proposed bioactivation pathway and evaluated their metabolic stabilities, CYP3A4 time-dependent inhibitory activities, and cytotoxicity. As a result, only a pyrimidine analog of NVP, which could avoid the formation of a reactive epoxide intermediate, did not inhibit CYP3A4. Outside of this compound, the other synthesized compounds, which could avoid the generation of a reactive quinone-methide intermediate, inhibited CYP3A4 equal to or stronger than NVP. The pyrimidine analog of NVP did not induce cytotoxicity in HepG2 and transchromosomic HepG2 cells, expressing major four CYP enzymes and CYP oxidoreductase. These results indicated that the epoxide intermediate of NVP might play an important role in NVP-induced liver injury.

    DOI： 10.1016/j.dmpk.2020.01.006

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  • Fullerene derivatives as dual inhibitors of HIV-1 reverse transcriptase and protease International journal

    Yasuno T, Ohe T, Kataoka H, Hashimoto K, Ishikawa Y, Furukawa K, Tateishi Y, Kobayashi T, Takahashi K, Nakamura S, Mashino T

    Bioorganic and Medicinal Chemistry Letters   31   127675 - 127675   2020

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：Bioorganic and Medicinal Chemistry Letters  

    © 2020 Elsevier Ltd In the present study, we newly synthesized three types of novel fullerene derivatives: pyridinium-type derivatives trans-3a and 4a-5b, piperidinium-type derivative 9, and proline-type derivatives 10a-12. Among the assessed compounds, 5a, 10e, 10f, 10i, 11a-d, and 12 were found to inhibit both HIV reverse transcriptase and HIV protease (HIV-PR), with IC50 values in the low micromolar range being observed. Regarding HIV-PR inhibition activity, proline-type derivatives 11a-11d and 12, bearing an alkyl chain between the hydroxylmethylcarbonyl (HMC) moiety and pyrrolidine ring, were more potent than other derivatives. This result might indicate that connecting HMC moieties with proline-type fullerene derivatives through properly sized alkyl chain leads to improved HIV-PR inhibitory activity.

    DOI： 10.1016/j.bmcl.2020.127675

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  • Inhibitors of the protein-protein interaction between phosphorylated p62 and Keap1 attenuate chemoresistance in a human hepatocellular carcinoma cell line Reviewed International journal

    Yasuda D., Ohe T., Takahashi, K., Imamura, R., Kojima H., Okabe T., Ichimura Y., Komatsu M., Yamamoto M., Nagano T., Mashino T.

    Free Radical Research   In Press, ( 11-12 )   859 - 871   2020

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    Resistance to anticancer agents has been an obstacle to developing therapeutics and reducing medical costs. Whereas sorafenib is used for the treatment of human hepatocellular carcinoma (HCC), resistance limits its efficacy. p62, a multifunctional protein, is overexpressed in several HCC cell lines, such as Huh-1 cells. Phosphorylated p62 (p-p62) inhibits the protein-protein interaction (PPI) between Keap1 and Nrf2, resulting in the Nrf2 overactivation that causes drug resistance. We have found a unique Nrf2 inactivator, named K67, that inhibited the PPI between Keap1 and p-p62 and attenuated sorafenib resistance in Huh-1 cells. Herein, we designed and synthesised novel K67 derivatives by modification of the substituent at the 4-position of the two benzenesulfonyl groups of K67. Although these new derivatives inhibited the Keap1-p-p62 PPI to a level comparable to or weaker than that of K67, the isopropoxy derivative enhanced the sensitivity of Huh-1 cells to sorafenib to a greater extent than K67 without any influence on the viability of Huh-7 cells, which is a non-resistant HCC cell line. The isopropoxy derivative also increased the sensitivity of Huh-1 cells to regorafenib, which suggests that this derivative has the potential to be used as an agent to overcome chemoresistance based on Nrf2 inactivation.

    DOI： 10.1080/10715762.2020.1732955

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  • <p>Synthesis and antitumor activity of novel pyridinium fullerene derivatives</p> Reviewed

    Takumi Yasuno, Tomoyuki Ohe, Hitomi Ikeda, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    International Journal of Nanomedicine   Volume 14   6325 - 6337   2019.8

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：Dove Medical Press Ltd.  

    DOI： 10.2147/IJN.S212045

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  • Synthesis of novel benzbromarone derivatives designed to avoid metabolic activation. Reviewed International journal

    Tomoyuki Ohe, Ryutaro Umezawa, Yumina Kitagawara, Daisuke Yasuda, Kyoko Takahashi, Shigeo Nakamura, Akiko Abe, Shuichi Sekine, Kousei Ito, Kentaro Okunushi, Hanae Morio, Tomomi Furihata, Naohiko Anzai, Tadahiko Mashino

    Bioorganic & medicinal chemistry letters   28 ( 23-24 )   3708 - 3711   2018.12

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    We synthesized six novel BBR derivatives that were designed to avoid metabolic activation via ipso-substitution and evaluated for their degree of toxicity and hURAT1 inhibition. It was found that all of the derivatives demonstrate lower cytotoxicity in mouse hepatocytes and lower levels of metabolic activation than BBR, while maintaining their inhibitory activity toward the uric acid transporter. We propose that these derivatives could serve as effective uricosuric agents that have much better safety profiles than BBR.

    DOI： 10.1016/j.bmcl.2018.10.023

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  • A 5-hydroxyoxindole derivative attenuates LPS-induced inflammatory responses by activating the p38-Nrf2 signaling axis. International journal

    Tomomi Niino, Kenji Tago, Daisuke Yasuda, Kyoko Takahashi, Tadahiko Mashino, Hiroomi Tamura, Megumi Funakoshi-Tago

    Biochemical pharmacology   155   182 - 197   2018.9

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：Biochemical Pharmacology  

    5-Hydroxyoxindole is a urinary metabolite of indole that exhibits antioxidant activity. In the present study, we found that a 5-hydroxyoxindole derivative (5-HI) significantly inhibited LPS-induced inflammatory effects in the murine macrophage cell line, RAW264.7. 5-HI induced the expression of the transcription factor, Nrf2, which is typically ubiquitinated by Keap1, an adaptor component of the ubiquitin E3 ligase complex, resulting in its proteasomal degradation. By utilizing Keap1-/- MEFs reconstituted with Keap1 mutants harboring substitutions in their major cysteine residues, we clarified the importance of Cys151 in Keap1 as a sensor for 5-HI in the induction of Nrf2 expression. Furthermore, 5-HI induced the activation of the MKK3/6-p38 pathway, which is required for the transcriptional activation of Nrf2. The knockdown of Nrf2 enhanced the LPS-induced expression of inflammatory mediators, including iNOS, NO, and CCL2, and effectively repressed the inhibitory effects of 5-HI on their expression. Although 5-HI and antioxidant N-acetyl cysteine (NAC) both reduced LPS-induced ROS generation, the treatment with NAC did not affect the LPS-induced expression of inflammatory mediators, suggesting that the anti-inflammatory activity of 5-HI mediated by Nrf2 is independent of redox control. Furthermore, when injected into mice with 5-HI, the expression of Nrf2 was significantly increased, and the LPS-induced mRNA expression of CXCL1, CCL2, TNFα, and IL-6 were remarkably inhibited in the kidneys, liver, and lungs, and the production of these cytokines in serum was effectively reduced. Collectively, these results suggest that 5-HI has potential in the treatment of inflammatory diseases through the activation of Nrf2.

    DOI： 10.1016/j.bcp.2018.06.021

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  • 医薬品としての物性向上を目指したKeap1-リン酸化p62結合阻害剤の創製

    中島 真央, 安田 大輔, 大江 知之, 高橋 恭子, 小松 雅明, 一村 義信, 今村 理世, 小島 宏建, 岡部 隆義, 長野 哲雄, 増野 匡彦

    日本薬学会年会要旨集   138年会 ( 2 )   114 - 114   2018.3

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  • Hit-to-lead in academia: Discovery of a protein-protein interaction inhibitor of Keap1-Nrf2

    Yasuda, D., Obata, R., Takahashi, K., Ohe, T., Mashino, T.

    Yakugaku Zasshi   138 ( 8 )   1059 - 1065   2018

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：Yakugaku Zasshi  

    © 2018 The Pharmaceutical Society of Japan. In the process of recent hit-to-lead studies, not only in industry but also in academia, early evaluation of metabolic properties has been one of the key aspects supporting a higher probability of success in drug discovery. In this review, we introduce the development of chemical seeds targeting the Kelch-like ECH-associated protein-1 (Keap1) as an example of an academic hit-to-lead study considering metabolic stability. Keap1 regulates the function of nuclear factor erythroid 2-related factor 2 (Nrf2), which induces various antioxidative or detoxification proteins. An inhibitor of protein-protein interaction (PPI) between Keap1 and Nrf2 to activate Nrf2 is expected to be a novel target for drug discovery. However, Nrf2 is also activated in several cancers, such as human hepatocellular carcinoma, and causes chemoresistance, which is mediated by phosphorylated p62/Sqstm1 (p-p62), an autophagy-related protein that also undergoes a PPI with Keap1. In this case, an Nrf2 suppressor could be used to attenuate drug resistance.We discovered inhibitors against the Nrf2-Keap1 PPI and p-p62-Keap1 PPI using high-throughput screening and established the synthetic routes for the hit compounds and their derivatives. Furthermore, we assessed the metabolic stability of both of the PPI inhibitors in human liver microsomes and identified the metabolic sites.

    DOI： 10.1248/yakushi.17-00211-5

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  • Discovery of benzo[g]indoles as a novel class of non-covalent Keap1-Nrf2 protein-protein interaction inhibitor

    Daisuke Yasuda, Akihiro Yuasa, Rika Obata, Mao Nakajima, Kyoko Takahashi, Tomoyuki Ohe, Yoshinobu Ichimura, Masaaki Komatsu, Masayuki Yamamoto, Riyo Imamura, Hirotatsu Kojima, Takayoshi Okabe, Tetsuo Nagano, Tadahiko Mashino

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   27 ( 22 )   5006 - 5009   2017.11

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    The Keap1-Nrf2 system is an attractive target for drug discovery regarding various unmet medical needs. Only covalent inhibitors for protein-protein interaction (PPI) between Keap1 and Nrf2 to activate Nrf2 have been approved or are under clinical trials, but such electrophilic compounds lack selectivity. Therefore, specific non-covalent Keap1-Nrf2 PPI inhibitors are expected to be safer Nrf2 activators. We found a novel class of non-covalent Keap1-Nrf2 PPI inhibitor that has a benzo[g]indole skeleton and an indole-3-hydroxamic acid moiety and that exhibits significant PPI inhibitory activity. Additionally, the benzo[g]indole-3-carbohydrazide derivatives were newly prepared. The benzo[g]indole derivatives showed a stronger Keap1-Nrf2 PPI inhibitory activity than Cpd16, a previously reported non-covalent PPI inhibitor. Moreover, most of the PPI inhibitors showed a high metabolic stability in a human microsome system with a low cytotoxicity against HepG2 cell lines, which suggests that novel benzo[g]indole-type Keap1-Nrf2 PPI inhibitors are expected to be biological tools or lead compounds for Nrf2 activators. (C) 2017 Elsevier Ltd. All rights reserved.

    DOI： 10.1016/j.bmcl.2017.10.008

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  • Strategic Drug Design to Avoid the Metabolic Activation of Hepatotoxic Drugs

    Tomoyuki Ohe, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN   137 ( 3 )   249 - 255   2017.3

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    Language：Chinese   Publishing type：Research paper (scientific journal)   Publisher：PHARMACEUTICAL SOC JAPAN  

    Adverse reactions are one of the most important issues in drug development, as well as in the therapeutic usage of drugs during the post-approval stage. Specifically, idiosyncratic adverse drug reactions (IDR) occur in only a small group of patients who are treated with certain drugs, and are unpredictable. It is widely accepted that drug-induced IDR is often associated with CYP-mediated bioactivation. Benzbromarone (BBR) is effective in the treatment of hyperuricemia, and has been used as an effective drug in Japan for a long time. However, BBR has been associated with hepatotoxicity, including fatal liver injury. We identified 2,6-dibromohydroquinone (DBH) and mono-debrominated catechol (CAT) as novel metabolites of BBR in human and rat liver microsomal systems, by comparison with chemically synthesized authentic compounds via ipso-substitution, which we previously discovered to be a unique metabolic reaction of substituted phenols by CYP. Furthermore, CAT, DBH and the oxidized form of DBH (DBBQ) were highly cytotoxic in human hepatocellular carcinoma cells, compared with BBR. We consider that the formation of these metabolites from BBR is linked to the mechanism involved in BBR-induced hepatotoxicity because catechols, hydroquinones, and their oxidized forms are known to be toxic.

    DOI： 10.1248/yakushi.16-00230-1

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  • Synthesis of Keap1-phosphorylated p62 and Keap1-Nrf2 protein-protein interaction inhibitors and their inhibitory activity

    Daisuke Yasuda, Mao Nakajima, Akihiro Yuasa, Rika Obata, Kyoko Takahashi, Tomoyuki Ohe, Yoshinobu Ichimura, Masaaki Komatsu, Masayuki Yamamoto, Riyo Imamura, Hirotatsu Kojima, Takayoshi Okabe, Tetsuo Nagano, Tadahiko Mashino

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   26 ( 24 )   5956 - 5959   2016.12

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    The Keapl-Nrf2 system is involved not only in biological defense but also in malignancy progression and chemoresistance. The ubiquitin-binding protein p62/Sqstm1 (p62), which is highly expressed in several cancers, competes with Nrf2 for Keap1 binding, leading to activation of Nrf2-mediated gene expression and survival of cancer cells. We had previously identified an inhibitor for the Keapl-phosphorylated-p62 (p-p62) protein-protein interaction (PPI), the acetonyl naphthalene derivative K67. In this study, we established facile synthetic routes for K67 and derivatives with various side chains on the C-2 position of naphthalene ring. K67 possessed high selectivity in the inhibition of Keap1-p-p62. Other derivatives showed potent Keapl-Nrf2 and Keap1-p-p62 PPI inhibitory activities, though the selectivity between the two activities was lower than K67. (C) 2016 Elsevier Ltd. All rights reserved.

    DOI： 10.1016/j.bmcl.2016.10.083

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  • Preparation and antioxidant/pro-oxidant activities of 3-monosubstituted 5-hydroxyoxindole derivatives

    Daisuke Yasuda, Kyoko Takahashi, Tomoyuki Ohe, Shigeo Nakamura, Tadahiko Mashino

    Cleft Palate-Craniofacial Journal   59 ( 6 )   165 - 173   2016.11

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Cleft Palate Craniofacial Association  

    Antioxidant treatments have been expected to be a novel thera-peutics for various oxidative stress-mediated disorders. Our previous study revealed that 5-hydroxyoxindole and its 3-phenacyl-3-hydroxy derivatives showed excellent antioxidant activities such as 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and lipid-peroxidation inhibitory activity. However, the DPPH radical scavenging activity of the 3,3-disubstituted derivatives was lower than that of the original 5-hydroxyoxindole. In the present study, we synthesized novel 3-monosubstituted 5-hydroxyoxindole derivatives that exhibited stronger DPPH radical scavenging activities and lipid peroxidation-inhibitory activities than the 3,3-disubstituted 5-hydroxyoxindoles. Moreover, the 3-monosubsti-tuted 5-hydroxyoxindole derivatives showed neither an iron-mediated pro-oxidant effect nor a remarkable cytotoxicity against HL-60 cell lines except some of the highly lipophilic compounds. These results indicate that 3-monosubstituted 5-hydroxyoxindoles can be used as a promising antioxidant scaffold for drug discovery.

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  • Preparation and antioxidant/pro-oxidant activities of 3-monosubstituted 5-hydroxyoxindole derivatives Reviewed

    Daisuke Yasuda, Kyoko Takahashi, Tomoyuki Ohe, Shigeo Nakamura, Tadahiko Mashino

    JOURNAL OF CLINICAL BIOCHEMISTRY AND NUTRITION   59 ( 3 )   165 - 173   2016.11

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    Antioxidant treatments have been expected to be a novel therapeutics for various oxidative stress-mediated disorders. Our previous study revealed that 5-hydroxyoxindole and its 3-phenacyl3-hydroxy derivatives showed excellent antioxidant activities such as 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and lipid-peroxidation inhibitory activity. However, the DPPH radical scavenging activity of the 3,3-disubstituted derivatives was lower than that of the original 5-hydroxyoxindole. In the present study, we synthesized novel 3-monosubstituted 5-hydroxyoxindole derivatives that exhibited stronger DPPH radical scavenging activities and lipid peroxidation-inhibitory activities than the 3,3disubstituted 5-hydroxyoxindoles. Moreover, the 3-monosubstituted 5-hydroxyoxindole derivatives showed neither an iron mediated pro-oxidant effect nor a remarkable cytotoxicity against HL-60 cell lines except some of the highly lipophilic compounds. These results indicate that 3-monosubstituted 5-hydroxyoxindoles can be used as a promising antioxidant scaffold for drug discovery.

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  • Development of Novel Inhibitors for Keap1-Nrf2 and Keap1-P62 Protein-Protein Interaction Reviewed

    Yasuda Daisuke, Yuasa Akihiro, Nakajima Mao, Yoshida Taketo, Obata Rika, Takahashi Kyoko, Ohe Tomoyuki, Ichimura Yoshinobu, Komatsu Masaaki, Yamamoto Masayuki, Imamura Riyo, Kojima Hirotatsu, Okabe Takayoshi, Nagano Tetsuo, Mashino Tadahiko

    FREE RADICAL BIOLOGY AND MEDICINE   100   S76   2016.11

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  • Novel fullerene derivatives as dual inhibitors of Hepatitis C virus NS5B polymerase and NS3/4A protease

    Hiroki Kataoka, Tomoyuki Ohe, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   26 ( 19 )   4565 - 4567   2016.10

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    We evaluated the Hepatitis C virus (HCV) NS5B polymerase and HCV NS3/4A protease inhibition activities of a new set of proline-type fullerene derivatives. All of the compounds had the potential to inhibit both the enzymes, indicating that the fullerene derivatives may be dual inhibitors against NS5B and NS3/4A and could be novel lead compounds for the treatment of HCV infections. (C) 2016 Elsevier Ltd. All rights reserved.

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  • p62/Sqstm1 promotes malignancy of HCV-positive hepatocellular carcinoma through Nrf2-dependent metabolic reprogramming Reviewed

    Tetsuya Saito, Yoshinobu Ichimura, Keiko Taguchi, Takafumi Suzuki, Tsunehiro Mizushima, Kenji Takagi, Yuki Hirose, Masayuki Nagahashi, Tetsuro Iso, Toshiaki Fukutomi, Maki Ohishi, Keiko Endo, Takefumi Uemura, Yasumasa Nishito, Shujiro Okuda, Miki Obata, Tsuguka Kouno, Riyo Imamura, Yukio Tada, Rika Obata, Daisuke Yasuda, Kyoko Takahashi, Tsutomu Fujimura, Jingbo Pi, Myung-Shik Lee, Takashi Ueno, Tomoyuki Ohe, Tadahiko Mashino, Toshifumi Wakai, Hirotatsu Kojima, Takayoshi Okabe, Tetsuo Nagano, Hozumi Motohashi, Satoshi Waguri, Tomoyoshi Soga, Masayuki Yamamoto, Keiji Tanaka, Masaaki Komatsu

    NATURE COMMUNICATIONS   7 ( 12030 )   1 - 16   2016.6

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    p62/Sqstm1 is a multifunctional protein involved in cell survival, growth and death, that is degraded by autophagy. Amplification of the p62/Sqstm1 gene, and aberrant accumulation and phosphorylation of p62/Sqstm1, have been implicated in tumour development. Herein, we reveal the molecular mechanism of p62/Sqstm1-dependent malignant progression, and suggest that molecular targeting of p62/Sqstm1 represents a potential chemotherapeutic approach against hepatocellular carcinoma (HCC). Phosphorylation of p62/Sqstm1 at Ser349 directs glucose to the glucuronate pathway, and glutamine towards glutathione synthesis through activation of the transcription factor Nrf2. These changes provide HCC cells with tolerance to anti-cancer drugs and proliferation potency. Phosphorylated p62/Sqstm1 accumulates in tumour regions positive for hepatitis C virus (HCV). An inhibitor of phosphorylated p62-dependent Nrf2 activation suppresses the proliferation and anticancer agent tolerance of HCC. Our data indicate that this Nrf2 inhibitor could be used to make cancer cells less resistant to anticancer drugs, especially in HCV-positive HCC patients.

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  • Novel Bioactivation Pathway of Benzbromarone Mediated by Cytochrome P450

    Yumina Kitagawara, Tomoyuki Ohe, Kumiko Tachibana, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    DRUG METABOLISM AND DISPOSITION   43 ( 9 )   1303 - 1306   2015.9

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    Benzbromarone (BBR) is a hepatotoxic drug, but the detailed mechanism of its toxicity remains unknown. We identified 2,6-dibromohydroquinone (DBH) and mono-debrominated catechol (2-ethyl-3-(3-bromo-4,5-dihydroxybenzoyl) benzofuran; CAT) as novel metabolites of BBR in rat and human liver microsomal systems by comparison with chemically synthesized authentic compounds, and we also elucidated that DBH is formed by cytochrome P450 2C9 and that CAT is formed mainly by CYP1A1, 2D6, 2E1, and 3A4. Furthermore, CAT, DBH, and the oxidized form of DBH are highly cytotoxic in HepG2 compared with BBR. Taken together, our data demonstrate that DBH, a novel reactive metabolite, may be relevant to BBR-induced hepatotoxicity.

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  • The human immunodeficiency virus-reverse transcriptase inhibition activity of novel pyridine/pyridinium-type fullerene derivatives

    Takumi Yasuno, Tomoyuki Ohe, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   25 ( 16 )   3226 - 3229   2015.8

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    In the present study, we describe the synthesis of a novel set of pyridine/pyridinium-type fullerene derivatives. The products were assessed for human immunodeficiency virus-reverse transcriptase inhibition activities. All novel fullerene derivatives showed potent human immunodeficiency virus-reverse transcriptase inhibition without cytotoxicity. (C) 2015 Elsevier Ltd. All rights reserved.

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  • Antioxidant activities of 5-hydroxyoxindole and its 3-hydroxy-3-phenacyl derivatives: The suppression of lipid peroxidation and intracellular oxidative stress

    Daisuke Yasuda, Kyoko Takahashi, Tomoyuki Ohe, Shigeo Nakamura, Tadahiko Mashino

    BIOORGANIC & MEDICINAL CHEMISTRY   21 ( 24 )   7709 - 7714   2013.12

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    The antioxidant activities of 5-hydroxyoxindole (1) and newly synthesized 3,5-dihydroxy-3-phenacyl-2-oxindole derivatives against rat liver microsome/tert-butylhydroperoxide system-induced lipid peroxidation and hydrogen peroxide-induced intracellular oxidative stress were investigated. Compound 1 and its derivatives showed significant suppression of lipid peroxidation and an intracellular oxidative stress. The effects of the more lipophilic derivatives tended to be greater than that of the original compound 1. The cytotoxicity of all of the oxindole derivatives on human promyelocytic leukemia HL60 cells was lower than that of 2,6-di(tert-butyl)-4-hydroxytoluene (BHT), a widely used phenolic antioxidant. These results show that compound 1 and its 3-substituted derivatives could be good lead candidates for future novel antioxidant therapeutics. (C) 2013 Elsevier Ltd. All rights reserved.

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  • Synthesis, radical scavenging activity and structure-activity relationship of uric acid analogs

    Daisuke Yasuda, Kyoko Takahashi, Tomohiro Kakinoki, Yoko Tanaka, Tomoyuki Ohe, Shigeo Nakamura, Tadahiko Mashino

    MEDCHEMCOMM   4 ( 3 )   527 - 529   2013.3

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    Uric acid (UA) is known to play an important role as an endogenous antioxidant. However, its insolubility in the serum is a risk for hyperuricemia. We assume that UA is an equivalent to hydroquinone or p-aminophenol, which can be oxidized to quinone/quinoimine and thus acts as a radical scavenger. Based on this hypothesis, a series of UA analogs was designed and synthesized. In the chemical radical scavenging assay, active compounds were considered as hydroquinone or p-aminophenol equivalents. A highly functionalized UA structure is not essential to have radical scavenging activity. Potent active 5-hydroxyindolinones (1a, 2a, and 3a) showed sufficient activity with high solubility and low cytotoxicity.

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  • Ipso substitution of bisphenol A catalyzed by microsomal cytochrome P450 and enhancement of estrogenic activity

    Shigeo Nakamura, Yoshito Tezuka, Atsuko Ushiyama, Chiaki Kawashima, Yumina Kitagawara, Kyoko Takahashi, Shigeru Ohta, Tadahiko Mashino

    TOXICOLOGY LETTERS   203 ( 1 )   92 - 95   2011.5

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    Bisphenol A (BPA), an industrial chemical with estrogenic activity, was investigated as a substrate for the ipso-metabolism catalyzed by microsomal cytochrome P450 (P450). BPA was expected to be transformed to a quinol via an ipso-addition reaction; however, hydroquinone (HQ) was detected as a metabolite via an ipso-substitution reaction. Isopropenylphenol (IPP) and hydroxycumyl alcohol (HCA) were also produced as eliminated metabolites by C-C bond scission via ipso-substitution. Incorporation of the (18)O atom to HCA from H(2) (18)O suggested the presence of a carbocation intermediate. Bulkiness of p-substituted group of BPA and/or stability of the eliminated carbocation intermediate may cause ipso-substitution of BPA. CYP3A4 and CYP3A5 showed higher activity for ipso-substitution. CYP2D6*1 also showed the activity; however, the other 9 isozymes did not. IPP showed ER-binding activity in the same degree of BPA. Furthermore, the ER-binding activity of HCA was about a hundred times greater than that of BPA. These results suggested that this new metabolic pathway contributes to the activation of the estrogenic activity of BPA. (C) 2011 Elsevier Ireland Ltd. All rights reserved.

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  • Interprofessional education at the Keio University Faculty of Pharmacy

    Yoshihiro Ehara, Yoshihiro Abe, Kazuko Fujimoto, Noriko Fukushima, Shiro Iijima, Satoko Ishikawa, Keiko Kishimoto, Mayumi Mochizuki, Kyoko Takahashi, Eriko Yokota, Shizuko Kobayashi

    Advanced Initiatives in Interprofessional Education in Japan: Japan Interprofessional Working and Education Network   57 - 63   2010

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    As part of a trial course on interprofessional education (IPE) at Keio University our Faculty of Pharmacy initiated a joint seminar with the university's medical and nursing departments in 2008. We had two joint seminars: one in June and another in October. In the seminars, students and participants actively discussed several issues with regard to the national and private health care systems and medical malpractice. They also listened to feedback lectures held by experts from the medical and social system. At Kyoritsu University of Pharmacy, we had already held similar joint seminars three times since 2006. The participants were not only from our school but from various universities around Japan, given that our school was then only a small college for pharmaceutical students. Our considerable experience in the field of small group learning (SGL) helped make these seminars a success. By making full use of the SGL method we have successfully lead the discussion sessions at the IPE seminars attended by students from various medical fields. After the merging of our small pharmaceutical college with Keio University, we continued holding joint seminars for the three medical faculties at Keio University. It has not been without tribulations, however. The newly created interprofessional seminars faced several problems. The seeming lack of interest shown by the medical school decreased the level of participation of medical students, while too many facilitators are required for such seminars. To resolve these issues, we have made some changes to future activities in this area. To start with, we plan to change the course from an elective to a required subject for the students of the three medical faculties in Keio University. © 2010 Springer Japan.

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  • In vitro free radical scavenging activity of platinum nanoparticles Reviewed

    Aki Watanabe, Masashi Kajita, Juewon Kim, Atsuhiro Kanayama, Kyoko Takahashi, Tadahiko Mashino, Yusei Miyamoto

    Nanotechnology   20 ( 45 )   455105 (9pp)   2009

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    A polyacrylic acid (PAA)-protected platinum nanoparticle species (PAA-Pt) was prepared by alcohol reduction of hexachloroplatinate. The PAA-Pt nanoparticles were well dispersed and homogeneous in size with an average diameter of 2.0 0.4nm (n = 200). We used electron spin resonance to quantify the residual peroxyl radical () generated from 2,2-azobis (2-aminopropane) dihydrochloride (AAPH) by thermal decomposition in the presence of O2 and a spectrophotometric method to quantify the residual 1,1-diphenyl-2- picrylhydrazyl (DPPH) radical. PAA-Pt scavenged these two radicals in a dose-dependent manner. Platinum was the functional component. PAA-Pt reduced the rate of oxygen consumption required for linoleic acid peroxidation initiated by generated from AAPH, indicating inhibition of the propagation of linolate peroxidation. A thiobarbituric acid test also revealed dose-dependent inhibition of the linolate peroxidation by PAA-Pt. Fifty micromolar platinum, as PAA-Pt, completely quenched 250 νM DPPH radical for 5min. Even when twice diluted in half, the PAA-Pt still quenched 100% of the 250νM DPPH radical. The scavenging activity of PAA-Pt is durable. These observations suggest that PAA-Pt is an efficient scavenger of free radicals. © IOP Publishing Ltd.

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  • Pyrrolidinium-type fullerene derivative-induced apoptosis by the generation of reactive oxygen species in HL-60 cells

    Chiho Nishizawa, Noriyuki Hashimoto, Sachiko Yokoo, Megumi Funakoshi-Tago, Tadashi Kasahara, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    FREE RADICAL RESEARCH   43 ( 12 )   1240 - 1247   2009

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    The biological activities of C-60-bis(N,N-dimethylpyrrolidinium iodide), a water-soluble cationic fullerene derivative, on human promyeloleukaemia (HL-60) cells were investigated. The pyrrolidinium fullerene derivative showed cytotoxicity in HL-60 cells. The characteristics of apoptosis, such as DNA fragmentation and condensation of chromatin in HL-60 cells, were observed by exposure to the pyrrolidinium fullerene derivative. Caspase-3 and -8 were activated and cytochrome c was also released from mitochondria. The generation of reactive oxygen species (ROS) by the pyrrolidinium fullerene derivative was observed by DCFH-DA, a fluorescence probe for the detection of ROS. Pre-treatment with alpha-tocopherol suppressed cell death and intracellular oxidative stress caused by the pyrrolidinium fullerene derivative. The apoptotic cell death induced by the pyrrolidinium fullerene derivative was suggested to be mediated by ROS generated by the pyrrolidinium fullerene derivative.

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  • Licochalcone A is a potent inhibitor of TEL-Jak2-mediated transformation through the specific inhibition of Stat3 activation

    Megumi Funakoshi-Tago, Kenji Tago, Chiho Nishizawa, Kyoko Takahashi, Tadahiko Mashino, Susumu Iwata, Hideo Inoue, Yoshiko Sonoda, Tadashi Kasahara

    BIOCHEMICAL PHARMACOLOGY   76 ( 12 )   1681 - 1693   2008.12

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    Aberrant activation of Jak/Stat signaling causes a number of hematopoietic disorders and oncogenesis, and therefore the effective inhibitors of the Jak/Stat signaling pathway may be therapeutically useful. TEL-Jak2 gene fusion, which has been identified in human leukemia, encodes a chimeric protein endowed with constitutive tyrosine kinase activity. Expression of TEL-Jak2 protects Ba/F3 cells from IL-3 withdrawal-induced apoptotic cell death and leads to IL-3-independent growth. However, its mechanisms remain to be only partially understood. Here, we first found that Licochalcone A, one of the flavonoids isolated from the root of Glycyrrhiza inflate, inhibited TEL-Jak2-mediated cell proliferation and survival in the absence of IL-3. Licochalcone A failed to inhibit the activity of TEL-Jak2, however, this induced apoptosis of TEL-Jak2-transformed cells with a much lower concentration in the absence of IL-3 than in the presence of IL-3. Interestingly, Licochalcone A significantly inhibited the phosphorylation and nuclear localization of Stat3, which is essential for TEL-Jak2-induced cell transformation. These data suggest that Licochalcone A is a specific inhibitor for Stat3 and would be employed for the treatment of various diseases caused by disorders of the Jak/Stat pathway. (c) 2008 Elsevier Inc. All rights reserved.

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  • 2,2 &apos;-pyridoin derivatives protect HL-60 cells against oxidative stress

    Masashi Hatanaka, Chiho Nishizawa, Tomohiro Kakinoki, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   18 ( 19 )   5290 - 5293   2008.10

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    Focusing on 2,2 &apos;-pyridoin (1, 1,2-di(2-pyridyl)-1,2-ethenediol) and its synthetic derivatives as the lead compound of the potent antioxidative enediol, their protective effect against oxidative stress was evaluated on the HL-60 cell system. 2,2 &apos;-Pyridoins showed no remarkable cytotoxic effect on HL-60 cells. The derivatives 1, 2, 3, 5, and 6 inhibited H(2)O(2)-induced cell death and intracellular oxidative stress more significantly than ascorbic acid. Since 2,2 &apos;-pyridoins are oxidized to the diketones, 2,2 &apos;-pyridils, in a protic solvent, the antioxidant activity of 2,2 &apos;-pyridils was also investigated. 2,2 &apos;-Pyridils showed antioxidant activity in the cell; however, the activity was lower than that of 2,2 &apos;-pyridoins. These results suggested that 2,2 &apos;-pyrdoin derivatives can be good cytoprotective agents against oxidative stress. (c) 2008 Elsevier Ltd. All rights reserved.

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  • Novel metabolic pathways of p-n-nonylphenol catalyzed by cytochrome p450 and estrogen receptor binding activity of new metabolites

    Yoshito Tezuka, Kyoko Takahashi, Tomoharu Suzuki, Shigeyuki Kitamura, Shigeru Ohta, Shigeo Nakamura, Tadahiko Mashino

    JOURNAL OF HEALTH SCIENCE   53 ( 5 )   552 - 561   2007.10

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    Nonylphenol, which is used industrially as a surfactant, is an endocrine-disrupting chemical (EDC) which has estrogenic activity. The novel biotransformation of nonylphenol was investigated, based on our previously reported ipso-metabolism of para-substituted phenols by cytochrome P450 (P450). Three novel metabolites of nonylphenol, i.e., nonylquinol, 4 '-hydroxynonanophenone (CO-NP) as benzyl-oxidized nonylphenol, and hydroquinone, were detected in a rat liver microsome reaction mixture. On the other hand, production of 1-(4 '-hydroxyphenyl)nonan-l-ol (OH-NP), namely benzyl-hydroxylated nonylphenol, was detected in a human liver microsome reaction mixture. The formation of all these metabolites was suppressed by the addition of P450 inhibitor. This showed that all nonylphenol metabolism was catalyzed by P450. To identify which P450 isoenzyme is involved in each reaction, fourteen human P450 (CYP) isozymes, CYP1A1, 1A2, 2A6, 2B6, 2C8, 2C9, 2C18, 2C19, 2D6, 2E1, 3A4, 3A5. 3A7, and CYP4A 11, were examined. CYP1A1, 1A2, and CYP2B6 effectively catalyzed the production of nonylquinol. CYP2B6 also catalyzed the benzyl-hydroxylation to give OH-NP Hydroquinone was formed mainly from OH-NP, not via CO-NP. We examined the estrogenic activity of these new metabolites by estrogen receptor (ER)-binding reporter gene assay. Nonylquinol, OH-NP and hydroquinone have no ER-binding activity. However, CO-NP showed the same level of estrogen receptor binding activity as nonylphenol. Moreover, the amount of CO-NP formed was small. Therefore, the novel metabolic pathways led overall to metabolic inactivation, as concerns the estrogenic activity of nonylphenol through the ER.

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  • Synthesis of novel amino acid-type fullerenes and their inhibition activity of HIV reverse transcriptase and HCV RNA polymerase. Reviewed

    Nakamura S, Ikegami N, Harada M, Shimotohno K, Takahashi K, Mashino T

    J Kyoritsu Univ Pharm   1   77-84 - 84   2006.3

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  • Metabolic conversion of 24-methyl-Delta(25)-cholesterol to 24-methylcholesterol in higher plants

    K Takahashi, K Nasu, T Mashino, M Morisaki, N Hara, Y Fujimoto

    BIOORGANIC & MEDICINAL CHEMISTRY   14 ( 3 )   732 - 738   2006.2

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    Feeding of chemically synthesized [27-C-13]codisterol ([27-C-13]2), [27-C-13]24-epicodisterol ([27-C-13]3), [23,24-H-2(2)]codisterol ([23,24-H-2(2)]2), and [26,27-H-2(6)]24-methyldesmosterol ([26,27-H-2(6)]8) to Oryza sativa cell cultures, followed by MS and NMR analysis of the biosynthesized dihydrobrassicasterol (9)/campesterol (10), revealed that both (24R)- and (24s)-epimers of 24-methyl-Delta(25)-cholesterol (2/3) were converted to 9 and 10 via the common intermediate 24-methyldesmosterol (8). (c) 2005 Elsevier Ltd. All rights reserved.

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  • Preparation and antioxidant activity of alpha-pyridoin and its derivatives

    M Hatanaka, K Takahashi, S Nakamura, T Mashino

    BIOORGANIC & MEDICINAL CHEMISTRY   13 ( 24 )   6763 - 6770   2005.12

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    Focusing on alpha-pyridoin (1, 1,2-di(2-pyridyl)-1,2-ethenediol) as the lead compound of the novel antioxidative enediol, we synthesized 5,5'- or 6,6'-bis-substituted derivatives of 1 from disubstituted pyridines. The antioxidant activity of 1 and its synthetic derivatives 2-7 was evaluated by DPPH (1,1-diphenyl-2-picrylhydrazyl radical) scavenging assay and inhibition of lipid peroxidation. In the DPPH assay, 1 exhibited an activity stronger than that of ascorbic acid, and 5,5'-dimethyl-(5) or 5,5'-dimethoxy-substituted derivatives (6) exhibited more potent activity than 1. The DPPH scavenging activities of alpha-pyridoins were correlated with their oxidation potential and thus the electron density of enediol. 5 and 6 effectively inhibited lipid peroxidation in the rat liver microsome/tert-butyl hydroperoxide system. Therefore, 5 and 6 serve as good candidates for a pharmacologically useful enediol antioxidant. (c) 2005 Elsevier Ltd. All rights reserved.

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  • 細胞内でホルムアルデヒドを放出する抗がん剤.

    高橋恭子

    ファルマシア   41 ( 11 )   1099 - 1100   2005.11

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  • Human immunodeficiency virus-reverse transcriptase inhibition and hepatitis C virus RNA-dependent RNA polymerase inhibition activities of fullerene derivatives

    T Mashino, K Shimotohno, N Ikegami, D Nishikawa, K Okuda, K Takahashi, S Nakamura, M Mochizuki

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   15 ( 4 )   1107 - 1109   2005.2

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    We examined the human immunodeficiency virus-reverse transcriptase and hepatitis C virus RNA-dependent RNA polymerase inhibition activities of cationic, anionic, and amino acid-type fullerene derivatives. Among the fullerene derivatives, the amino acid-type fullerene derivative was the most efficient in human immunodeficiency virus-reverse transcriptase inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

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  • Antibacterial and antiproliferative activity of cationic fullerene derivatives

    T Mashino, D Nishikawa, K Takahashi, N Usui, T Yamori, M Seki, T Endo, M Mochizuki

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   13 ( 24 )   4395 - 4397   2003.12

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    We examined the antibacterial and antiproliferative activities of alkylated C-60-bis(N,N-dimethylpyrrolidinium iodide) derivatives. The fullerene derivatives inhibited bacteria and cancer cell growth effectively. However, the fullerene derivatives with a long alkyl chain did not show antibacterial activity. (C) 2003 Elsevier Ltd. All rights reserved.

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  • Biosynthesis of phytoecdysteroids in Ajuga hairy roots: Clerosterol as a precursor of cyasterone, isocyasterone and 29-norcyasterone Reviewed

    Okuzumi, K., Hara, N., Fujimoto, Y., Yamada, J., Nakamura, A., Takahashi, K., Morisaki, M.

    Tetrahedron Letters   44 ( 2 )   323-326   2003.2

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  • Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol

    K Takahashi, K Hashimoto, A Fujiyama, J Yamada, N Kobayashi, M Morisaki, S Nakano, N Hara, Y Fujimoto

    TETRAHEDRON LETTERS   44 ( 2 )   341 - 344   2003.1

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    Feeding of the chemically prepared [24-C-13, 24-H-2]desmosterol to cell-free systems derived from rat liver and silkworm gut and to cultured cells of Oryza sativa followed by deuterium-decoupled H-1,C-13 shift correlation NMR analysis of the biosynthesized cholesterol revealed the stereospecific incorporation of hydrogen atoms from the re-face of the C-24 position of desmosterol. (C) 2002 Elsevier Science Ltd. All rights reserved.

    DOI： 10.1016/S0040-4039(02)02567-4

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  • Stereochemical fate of C-26 and C-27 during the conversion of isofucosterol to sitosterol and of 24-methylenecholesterol to campesterol and dihydrobrassicasterol in Oryza sativa cell cultures

    K Nasu, K Takahashi, M Morisaki, Y Fujimoto

    PHYTOCHEMISTRY   54 ( 4 )   381 - 385   2000.6

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    Administration of pro-R-methyl-C-13-labeled isofucosterol to cultured cells of Oryza sativa revealed that the pro-R and pro-S methyls at C-25 become the pro-R and pro-S methyls at C-25 of sitosterol, respectively. Similar administration experiments using pro-S-methyl-C-13-labeled 24-methylenecholesterol established that the pro-R and pro-S methyls at C-25 of 24-methylenecholesterol become the pro-R and pro-S methyls of campesterol, and the pro-S and pro-R methyls of dihydrobrassicasterol, respectively. These results are compatible with our recently proposed 'syn-S(E)2' mechanism' for double bond isomerization of Delta(24(28)) into Delta(24(25)). (C) 2000 Elsevier Science Ltd. All rights reserved.

    DOI： 10.1016/S0031-9422(00)00122-9

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  • Biosynthesis of sterols and ecdysteroids in Ajuga hairy roots

    Y Fujimoto, K Ohyama, K Nomura, R Hyodo, K Takahashi, J Yamada, M Morisaki

    LIPIDS   35 ( 3 )   279 - 288   2000.3

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER OIL CHEMISTS SOC A O C S PRESS  

    Hairy roofs of Ajuga reptans var, atropurpurea produce clerosterol, 22-dehydroclerosterol, and cholesterol as sterol constituents, and 20-hydroxyecdysone, cyasterone, isocyasterone, and 29-norcyasterone as ecdysteroid constituents. To better understand the biosynthesis of these steroidal compounds, we carried out feeding studies of variously H-2- and C-13-labeled sterol substrates with Ajuga hairy roots. In this article, we review our studies in this field. Feeding of labeled desmosterols, 24-methylenecholesterol, and C-13(2)-acetate established the mechanism of the biosynthesis of the two C-29-sterols and a newly accumulated codisterol, including the metabolic correlation of C-26 and C-27 methyl groups. in Ajuga hairy roots, 3 alpha-, 4 alpha-, and 4 beta-hydrogens of cholesterol were all retained at their original positions after conversion into 20-hydroxyecdysone, in contrast to the observations in a fern and an insect. Furthermore, the origin of 5 beta-H of 20-hydroxyecdysone was found to be C-6 hydrogen of cholesterol exclusively, which is inconsistent with the results in the fern and the insect. These data strongly support the intermediacy of 7-dehydrocholesterol 5 alpha,6 alpha-epoxide. Moreover, 7-dehydrocholesterol, 3 beta-hydroxy-5 beta-cholest-7-en-6-one (5 beta-ketol), and 3 beta,14 alpha-dihydroxy-5 beta-cholest-7-en-6-one (5 beta-ketodiol) were converted into 20-hydroxyecdysone. Thus, the pathway cholesterol --&gt; 7-dehydrocholesterol --&gt; 7-dehydrocholesterol 5 alpha,6 alpha-epoxide --&gt; 5 beta-ketol --&gt; 5 beta-ketodiol is proposed for the early stages of 20-hydroxyecdysone biosynthesis. 3 beta-Hydroxy-5 beta-cholestan-6-one was also incorporated into 20-hydroxyecdysone, suggesting that the introduction of a 7-ene function is not necessarily next to cholesterol. C-25 Hydroxylation during 20-hydroxyecdysone biosynthesis was found to proceed with ca. 70% retention and 30% inversion. Finally, clerosterol was shown to be a precursor of cyasterone and isocyasterone.

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  • Synthesis of artificial HMG-CoA reductase inhibitors based on the olefination strategy

    Hiyama, T., Minami, T., Takahashi, K.

    Bulletin of the Chemical Society of Japan   68 ( 1 )   1995

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    DOI： 10.1246/bcsj.68.364

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  • Synthesis of an artificial HMG-CoA reductase inhibitor NK-104 via a hydrosilylation-cross-coupling reaction

    Takahashi, K., Minami, T., Ohara, Y., Hiyama, T.

    Bulletin of the Chemical Society of Japan   68 ( 9 )   1995

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    DOI： 10.1246/bcsj.68.2649

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  • Stereoselective reduction of β,δ-diketo esters derived from tartaric acid. A facile route to optically active 6-oxo-3,5-syn-isopropylidenedioxyhexanoate, a versatile synthetic intermediate of artificial HMG Co-A reductase inhibitors.

    Minami, T., Takahashi, K., Hiyama, T.

    Tetrahedron Letters   34 ( 3 )   1993

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    Publishing type：Research paper (scientific journal)  

    DOI： 10.1016/0040-4039(93)85115-D

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  • Convenient synthesis of optically active abscisic acid and xanthoxin

    Sakai, K., Takahashi, K., Nukano, T.

    Tetrahedron   48 ( 38 )   1992

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    Publishing type：Research paper (scientific journal)  

    DOI： 10.1016/S0040-4020(01)80491-9

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  • Role of Cholesterol 10-Methyl Group and Effect of “Extra” 14-Methyl Group on Silkworm Growth and Development

    Mamiya, M., Takahashi, K., Eguchi, S., Morisaki, M.

    Chemical and Pharmaceutical Bulletin   37 ( 7 )   1989

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    Publishing type：Research paper (scientific journal)  

    DOI： 10.1248/cpb.37.1930

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  • Synthesis of 14α-Methylcholesterol

    Takahashi, K., Usami, K., Takahashi, T., Okada, T., Morisaki, M.

    Chemical and Pharmaceutical Bulletin   35 ( 8 )   1987

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    Publishing type：Research paper (scientific journal)  

    DOI： 10.1248/cpb.35.3467

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Books

  • Interprofessional Education at the Keio University Faculty of Pharmacy, in: Advanced Initiatives in Interprofessional Education in Japan" (ed. by Watanabe H, Koizumi M)."

    Ehara Y, Abe Y, Fujimoto K, Fukushima N, Iijima S, Ishikawa S, Kishimoto K, Mochizuki M, Takahashi K, Yokota E, Kobayashi S（ Role： Joint authorpp57-63）

    Springer, Tokyo, Berlin, Heidelberg, New York  2010.2 

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Misc.

  • ADME evaluation and derivatization of the oxicam analogue IY104 for the treatment of Parkinson’s disease.

    鶴岡航太朗, 高橋恭子, 中村成夫, 熊谷直哉, 増野匡彦, 大久保知子, 眞鍋貴行, 田崎嘉一, 大江知之

    日本薬学会年会要旨集(Web)   142nd   2022

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  • Development of novel fluorescent labeled trapping reagent to detect reactive acyl glucuronides

    柴崎智香子, 大江知之, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会年会要旨集(Web)   141st   2021

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  • Development of novel heteroaromatic analogs of oxicam ring A as drug for Parkinson’s disease.

    鶴岡航太朗, 小町元輝, 鈴木啓太, 高橋恭子, 中村成夫, 大江知之, 大久保知子, 眞鍋貴之, 田崎嘉一, 増野匡彦

    日本薬学会年会要旨集(Web)   141st   2021

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  • Metabolic ipso-Substitution of 5-Substituted-2-oxindole Catalyzed by Cytochrome P450

    公平実希, 大江知之, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会年会要旨集(Web)   141st   2021

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  • Development of multi-targeting pyridinium-type C60 derivatives for treating HIV/HCV co-infection

    小林透威, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会年会要旨集(CD-ROM)   140th   2020

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  • Novel method to detect reactive acyl glucuronide metabolites with trapping reagents

    柴崎智香子, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会年会要旨集(CD-ROM)   140th   2020

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  • Synthesis and biological evaluation of novel diclofenac analogs designed to avoid metabolic activation

    立石泰寛, 大江知之, 小川真依, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会年会要旨集(CD-ROM)   140th   2020

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  • HIVプロテアーゼ/逆転写酵素,HCV NS5Bを標的とするピリジニウム型C60誘導体の創製

    小林透威, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会関東支部大会講演要旨集   64th   2020

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  • アカデミアにおける Hit-to-Lead の実践 ~Keap1-Nrf2 タンパク間相互作用阻害剤の創製~ Reviewed

    安田大輔, 小畠りか, 高橋恭子, 大江知之, 増野匡彦

    薬学雑誌   138 ( 8 )   1059 - 1065   2018.8

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  • 医薬品としての物性向上を目指したKeap1-リン酸化p62結合阻害剤の創製

    中島 真央, 安田 大輔, 大江 知之, 高橋 恭子, 小松 雅明, 一村 義信, 今村 理世, 小島 宏建, 岡部 隆義, 長野 哲雄, 増野 匡彦

    日本薬学会年会要旨集   138年会 ( 2 )   114 - 114   2018.3

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  • 代謝活性化を回避した新規ベンズブロマロン類縁体の合成およびその毒性評価

    梅沢隆太郎, 北川原弓奈, 高橋恭子, 中村成夫, 阿部晃子, 関根修一, 伊藤晃成, 大江知之, 増野匡彦

    日本薬学会関東支部大会講演要旨集   61st   2017

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  • Cyclooxygenase(COX)阻害作用を持たないmeloxicam類縁体もMPP+誘発SH-SY5Y神経細胞死を抑制する

    坂口 智己, 小野 尚志, 海東 和麻, 山本 譲, 神山 直也, 高橋 恭子, 粟屋 敏雄, 福土 将秀, 大江 知之, 増野 匡彦, 田崎 嘉一

    日本薬学会年会要旨集   135年会 ( 3 )   80 - 80   2015.3

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  • Synthesis and Structure-Activity Relationship on Antioxidant Activity of Uric Acid Analogues

    K. Takahashi, T. Kakinoki, D. Yasuda, S. Nakamura, T. Mashino

    FREE RADICAL RESEARCH   43   81 - 81   2009

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Presentations

  • Discovery and synthesis of a novel non-covalent inhibitor for protein-protein interaction between Nrf2 and Keap1. International conference

    YASUDA Daisuke, OHE Tomoyuki, OBATA Rika, TAKAHASHI Kyoko, MASHINO Tadahiko, KOMATSU Masaaki, ICHIMURA Yoshinobu, YAMAMOTO Masayuki, IMAMURA Riyo, KOJIMA Hirotatsu, OKABE Takayoshi, HNAGANO Tetsuo

    THE INTERNATIONAL CHEMICAL CONGRESS OF PACIFIC BASIN SOCIETIES 2015  2015.12  American Chemical Society

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    Venue：Honolulu, USA  

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  • アルコキシカルボニル-2-インダノン骨格を有する抗酸化化合物の探索.

    西野優希, 松本麻里子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第128年会  2008.3 

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    Venue：横浜  

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  • 新規環状ジペプチド化合物の合成およびラジカル消去活性と置換基効果

    轟龍馬, 槇田智史, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第136年会  2016.3  日本薬学会

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    Venue：横浜  

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  • アルキル基導入ピロリジニウム型フラーレン誘導体のアポトーシス誘導効果.

    横尾祥子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第128年会  2008.3 

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    Venue：横浜  

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  • β-ケトエステル構造を有する新規抗酸化剤.

    高橋恭子, 西野優希, 松本麻里子, 横川めぐみ, 中村成夫, 増野匡彦

    日本酸化ストレス学会 第61回学術集会  2008.6 

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    Venue：京都  

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  • 5位メチル化によるnevirapineの代謝活性化の回避

    伊賀渉, 巴川暢子, 藤澤眞太郎, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第136年会  2016.3  日本薬学会

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    Venue：横浜  

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  • Bisacodyl の新規代謝物の探索——脱離生成物からの更なるhydroquinoneの生成.

    土門周, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第128年会  2008.3 

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    Venue：横浜  

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  • ピリジニウム側鎖を有する新規ジカチオン型C60誘導体のHIV逆転写酵素阻害活性およびがん細胞増殖抑制効果

    安野 拓実, 高橋 恭子, 大江 知之, 中村 成夫, 増野 匡彦

    日本薬学会第136年会  2016.3  日本薬学会

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    Venue：横浜  

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  • 抗酸化活性を有する2-インダノン誘導体のAβ誘発細胞死保護効果

    平井 翔子, 藤田 亮輔, 高橋 恭子, 中村 成夫, 大江 知之, 増野 匡彦

    日本薬学会第136年会  2016.3  日本薬学会

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    Venue：横浜  

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  • ヒト肝ミクロソームによるビスフェノールA ipso 位代謝物の生成.

    牛山温子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第128年会  2008.3 

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    Venue：横浜  

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  • 2-アリール-1,3-ジカルボニル化合物の抗酸化活性.

    横川めぐみ, 西野優希, 高橋恭子, 中村成夫, 増野匡彦

    第52回日本薬学会関東支部大会  2008.10 

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    Venue：東京  

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  • シスプラチン誘発細胞毒性に対する環状ジペプチド化合物の保護効果

    槇田智史, 池貴幸, 安田大輔, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第136年会  2016.3  日本薬学会

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    Venue：横浜  

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  • Apoptosis Induction on HL-60 Cell by Cationic Fullerene Derivatives.

    横尾祥子, 西澤千穂, 高橋恭子, 中村成夫, 増野匡彦

    第35回 フラーレン・ナノチューブ総合シンポジウム  2008.8 

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    Venue：東京  

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  • 内分泌攪乱物質 Methoxychlor および類縁体の cytochrome P450 による新規代謝物の探索 - ipso 置換反応による Hydroquinone の生成 -."

    牛山温子, 田中悠貴, 高橋恭子, 中村成夫, 増野匡彦

    フォーラム2008 衛生薬学・環境トキシコロジー  2008.10 

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    Venue：熊本  

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  • HCV RNAポリメラーゼ阻害活性を有するプロリン型フラーレン誘導体の抗酸化活性

    片岡裕樹, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第136年会  2016.3  日本薬学会

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    Venue：横浜  

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  • 新規非共有結合性Keap1-Nrf2結合阻害剤の探索と誘導体合成

    安田大輔, 大江知之, 湯浅章弘, 小畠りか, 高橋恭子, 小松雅明, 一村義信, 山本雅之, 今村理世, 小島宏建, 岡部隆義, 長野哲雄, 増野匡彦

    第11回日本ケミカルバイオロジー学会年会  2016.6  日本ケミカルバイオロジー学会

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    Venue：京都  

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  • P450化学モデル系による内分泌攪乱物質メトキシクロル類縁体の新規酸化開裂反応および生体内酸化反応との比較.

    中村成夫, 牛山温子, 田中悠貴, 高橋恭子, 増野匡彦

    第41回酸化反応討論会  2008.11 

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    Venue：福岡  

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  • HCVポリメラーゼ/プロテアーゼを阻害する二重標的型フラーレン誘導体の創製

    片岡裕樹, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    第60回日本薬学会関東支部大会  2016.9  日本薬学会関東支部会

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    Venue：東京  

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  • 抗酸化活性2,2'-Pyridoin 類縁体のNFkB 活性化抑制効果.

    高橋恭子, 畑中雅史, 井上巧, 伊藤舞, 中村成夫, 増野匡彦

    第 23 回日本酸化ストレス学会関東支部会  2008.12 

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    Venue：東京  

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  • ヒダントイン環を活性部位とする抗酸化剤のラジカル消去活性

    岡崎希望, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第31回日本酸化ストレス学会関東支部会  2016.12  日本酸化ストレス学会関東支部

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    Venue：東京  

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  • 抗HCV薬を目指した 新規フラーレン誘導体の合成.

    森裕美子, 田丸友裕, 下遠野久美子, 高橋恭子, 中村成夫, 増野匡彦

    第52回日本薬学会関東支部大会  2008.10 

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    Venue：東京  

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  • 酸化ストレス応答性新規Keap1-Nrf2結合阻害剤の創製

    湯浅章弘, 安田大輔, 大江知之, 小畠りか, 高橋恭子, 小松雅明, 一村義信, 山本雅之, 今村理世, 小島宏建, 岡部隆義, 長野哲雄, 増野匡彦

    第69回 日本酸化ストレス学会学術集会  2016.8  日本酸化ストレス学会

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    Venue：仙台  

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  • 抗酸化活性を有する尿酸誘導体の合成と構造活性相関, 酸化ストレスに対する細胞保護効果.

    柿木智宏, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    第27 回メディシナルケミストリーシンポジウム  2008.11 

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    Venue：大阪  

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  • ヒダントイン型抗酸化剤のラジカル消去活性と消去機構

    岡崎希望, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第60回日本薬学会関東支部大会  2016.9  日本薬学会関東支部会

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    Venue：東京  

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  • 5位に脂溶性置換基を有するプロリン型フラーレン誘導体のHIV逆転写酵素阻害活性.

    竹内由紀, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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    Venue：京都  

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  • ネビラピンA環及びB環の変換により代謝活性化を回避した新規誘導体の合成

    立石泰寛, 藤澤眞太郎, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第137年会  2017.3  日本薬学会

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    Venue：仙台  

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  • 炎症性刺激に対するフラーレン誘導体のNFkB 活性化抑制効果の検討.

    井上巧, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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    Venue：京都  

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  • HCVポリメラーゼ/プロテアーゼ二重阻害活性を有するフラーレン誘導体の細胞内HCV複製阻害及び酸化ストレス抑制効果

    片岡裕樹, 上田優輝, 髙橋恭子, 大江知之, 中村成夫, 加藤宣之, 増野匡彦

    日本薬学会第137年会  2017.3  日本薬学会

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  • 生命の大切さを知るために:患者から学ぶ.

    福島紀子, 岸本桂子, 小林静子, 服部豊, 千葉康司, 松山賢治, 望月眞弓, 飯島史朗, 石川さと子, 板垣悦子, 片山和浩, 高橋恭子, 小林典子, 川村和美

    日本薬学会第129年会  2009.3 

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    Venue：京都  

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  • 薬剤耐性がん治療薬を目指した新規ジカチオン型C60誘導体の創製

    安野拓実, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第137年会  2017.3  日本薬学会

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    Venue：仙台  

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  • ラジカル消去活性を有するインドール型環状ジペプチドの構造展開

    轟龍馬, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第137年会  2017.3  日本薬学会

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  • 新規尿酸アナログの抗酸化活性と構造活性相関.

    柿木智宏, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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    Venue：京都  

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  • 2-アセチルインダノン類の抗酸化活性.

    横川めぐみ, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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    Venue：京都  

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  • HIV逆転写酵素及びプロテアーゼを阻害する 多標的型新規フラーレン誘導体の創製

    橋本航匠, 片岡裕樹, 加藤舞, 秋葉智紘, 安野拓実, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第137年会  2017.3  日本薬学会

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  • 抗HCV 薬を目指したスルホンアミド型フラーレン誘導体の探索.

    森裕美子, 田丸友裕, 下遠野久美子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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  • 抗がん薬を⽬指した新規ピリジニウム型C60 誘導体の創製

    安野 拓実, 高橋 恭子, 大江 知之, 中村 成夫, 渡部匡史, 藤室雅弘, 増野 匡彦

    第7回ナノカーボンバイオシンポジウム  2017.9  第7回ナノカーボンバイオシンポジウム

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    Venue：京都  

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  • 代謝活性化を回避した新規ベンズブロマロン類縁体の合成およびその毒性評価

    梅沢 隆太郎, 北川原 弓奈, 高橋 恭子, 中村 成夫, 阿部 晃子, 関根 修一, 伊藤 晃成, 大江 知之, 増野 匡彦

    第61回日本薬学会関東支部大会  2017.9  第61回日本薬学会関東支部大会

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    Venue：東京  

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  • アルキル基導入ピロリジウム型フラーレン誘導体の細胞内酸化ストレス惹起効果.

    横尾祥子, 小泉由起, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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    Venue：京都  

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  • 医薬品としての物性向上を目指したKeap1-リン酸化p62結合阻害剤の創製

    中島真央, 安田大輔, 大江知之, 高橋恭子, 小松雅明, 一村義信, 今村理世, 小島宏建, 岡部隆義, 長野哲雄, 増野匡彦

    日本薬学会第138年会  2018.3  日本薬学会第138年会

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  • シクロペンタンを有する新規水溶性フラーレン誘導体の合成.

    近藤祥子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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  • 生命の大切さを知るために:統合型カリキュラムによるヒューマニズム教育.

    阿部芳廣, 飯島史朗, 石川さと子, 江原吉博, 岸本桂子, 小林静子, 高橋恭子, 福島紀子, 望月眞弓, 横田恵理子

    日本薬学会第129年会  2009.3 

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  • グルクロン酸抱合経由の代謝活性化を回避したジクロフェナク類縁体の創製

    山田晶子, 大江知之, 小川真依, 髙橋恭子, 中村成夫, 増野匡彦

    日本薬学会第138年会  2018.3  日本薬学会第138年会

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  • 内分泌攪乱物質 Methoxychlor および類縁体の cytochrome P450 による新規代謝物の探索 - ipso 置換反応による Hydroquinone の生成 -."

    牛山温子, 田中悠貴, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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  • HIV 逆転写酵素阻害活性を有するジドブジン結合型新規フラーレン誘導体の創製

    正堺 雄大, 大江 知之, 高橋 恭子, 中村 成夫, 増野匡彦

    第61回日本薬学会関東支部大会  2017.9  第61回日本薬学会関東支部大会

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    Venue：東京  

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  • 抗 HIV 薬を目指した新規ピリジニウム型フラーレン誘導体の創製

    安野 拓実, Halil Ibrahim Chiftch, 高橋 恭子, 藤田美歌子, 大江 知之, 中村 成夫, 増野 匡彦

    第35回メディシナルケミストリーシンポジウム  2017.11  第35回メディシナルケミストリーシンポジウム

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  • シトクロムP450によるキノール体の代謝反応 -キノール体のNIHシフト中間体としての可能性の検討-.

    榎本千聡, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第129年会  2009.3 

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  • Synthesis of novel pyridine/pyridinium-type fullerene derivatives with human immunodeficiency virus-reverse transcriptase inhibition activity International conference

    YASUNO Takumi, TAKAHASHI Kyoko, OHE Tomoyuki, NAKAMURA Shigeo, MASHINO Tadahiko

    THE INTERNATIONAL CHEMICAL CONGRESS OF PACIFIC BASIN SOCIETIES 2015  2015.12  American Chemical Society

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    Venue：Honolulu, USA  

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  • コレステロール生合成における側鎖還元反応の立体化学.

    高橋恭子, 橋本献一郎, 藤山綾子, 増野匡彦, 藤本善徳, 森崎益雄

    第46回日本薬学会関東支部大会  2002.10 

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    Venue：東京  

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  • 内分泌攪乱物質diethylstilbestrolのipso位代謝反応の検討.

    川島千明, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • 尿酸類縁体のperoxynitrite消去活性.

    伊藤舞, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • 環境ホルモン ノニルフェノールの新規代謝物.

    手塚淑人, 高橋恭子, 山田七海, 増野匡彦

    第46回日本薬学会関東支部大会  2002.10 

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    Venue：東京  

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  • 共役ケトンを有するステロイドのアポトーシス誘導効果.

    小川広志, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • Benzoinを基本骨格とする抗酸化剤の開発.

    増野匡彦, 畑中雅史, 青沼育実, 高橋恭子

    第22回メディシナルケミストリーシンポジウム  2002.11 

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    Venue：静岡  

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  • 6-Phenacyl-3-pyridinol 誘導体の抗酸化活性.

    畑中雅史, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • 長鎖アルキル基を側鎖に持つC60-N,N-dimethylpyrrolidine誘導体のがん細胞増殖抑制効果.

    西川大, 高橋恭子, 田中ちはる, 薄井典子, 望月正隆, 増野匡彦

    第46回日本薬学会関東支部大会  2002.10 

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    Venue：東京  

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  • 溶解度の高い尿酸類縁体の抗酸化活性.

    安田大輔, 柿木智宏, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • Pyridoin 誘導体の抗酸化活性.

    畑中雅史, 高橋恭子, 青沼育実, 増野匡彦

    第46回日本薬学会関東支部大会  2002.10 

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    Venue：東京  

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  • NFκB 活性化に対するフラーレン誘導体の抑制効果.

    井上巧, 伊藤雅之, 山名修一, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • ピリジン環に官能基を有するa-pyridoin の抗酸化活性.

    畑中雅史, 青沼育実, 高橋恭子, 増野匡彦

    日本薬学会第123年会  2003.3 

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    Venue：長崎  

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  • 尿酸類縁体のperoxynitriteとnitric oxide消去活性.

    伊藤舞, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    第63回日本酸化ストレス学会学術集会  2010.6 

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    Venue：神奈川  

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  • アルキル側鎖を有するC60-bis(N,N-dimethylpyrrolidinium iodide) 誘導体の大腸菌生育阻害効果.

    西川大, 高橋恭子, 薄井典子, 望月正隆, 増野匡彦

    日本薬学会第123年会  2003.3 

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    Venue：長崎  

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  • シトクロムP450によるp-置換フェノール代謝におけるNIH-shiftの新規反応機構.

    榎本千聡, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • 昆虫（カイコ）におけるdesmosterolの24-エン還元反応の立体化学.

    中野さやか, 名和哲兵, 原典行, 藤本善徳, 高橋恭子, 橋本献一郎, 藤山綾子, 森崎益雄

    日本化学会第83春季年会  2003.3 

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    Venue：東京  

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  • 1-アセチル-2-インダノン誘導体のラジカル消去活性と細胞内酸化ストレス抑制効果.

    横川めぐみ, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • 7-Hydroxy-androst-4-en-3,6,17-trioneの抗酸化活性.

    高橋恭子, 鈴木里佳, 増野匡彦

    日本薬学会第123年会  2003.3 

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    Venue：長崎  

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  • 可溶性Carbon Nanotube 誘導体の合成.

    小野寺明, 石橋史子, 高橋恭子, 増野匡彦

    日本薬学会第123年会  2003.3 

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    Venue：長崎  

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  • プロリン型フラーレン誘導体による HIV 増殖抑制効果.

    篠原舞, 竹内由紀, 高橋恭子, 藤田美歌子, 大塚雅巳, 中村成夫, 増野匡彦

    第29回メディシナルケミストリーシンポジウム  2010.11 

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    Venue：京都  

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  • 第25回日本酸化ストレス学会関東支部大会.

    前田和貴子, 幸田愛未, 高橋恭子, 中村成夫, 増野匡彦

    第17回時間生物学会学術大会  2010.12 

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    Venue：東京  

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  • Bacteriostatic effect of C60-(N, N-dimethylpyrrolidinium iodide) derivatives. International conference

    Mashino T, Nishikawa D, Takahashi K, Usui N, Mochizuki M

    203th Elecorochemical Society Meeting  2003.5 

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    Venue：Paris, France  

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  • フラーレン誘導体による細胞内活性酸素生成機構の解析.

    小泉由起, 高橋恭子, 中村成夫, 増野匡彦

    第54回日本薬学会関東支部大会  2010.10 

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    Venue：東京  

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  • エストロゲン作用をもつ化合物およびおよびその類縁体のP450依存新規代謝物の検討.

    川島千明, 高橋恭子, 中村成夫, 増野匡彦

    第54回日本薬学会関東支部大会  2010.10 

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    Venue：東京  

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  • エストロゲンレセプター結合能を有する置換フェノール類の新規代謝物検索と生理活性の検討.

    手塚淑人, 高橋恭子, 山田七海, 太田茂, 増野匡彦

    日本薬学会第123年会  2003.3 

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    Venue：長崎  

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  • ピロリジニウム型フラーレン誘導体によるミトコンドリアでの活性酸素生成.

    小泉由起, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第131年会  2011.3 

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    Venue：静岡  

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  • Antibacterial and Antiproliferative Activity of C60-(N, N-Dimethylpyrrolidinium Iodide) Derivatives. International conference

    Mashino T, Nishikawa D, Takahashi K, Yamori T, Endo T, Mochizuki M

    204th Elecorochemical Society Meeting,  2003.10 

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    Venue：Orland, USA  

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  • Antioxidant activity of a-pyridoin derivatives. International conference

    Hatanaka M, Takahashi K, Mashino T

    International Joint Meeting on Food Factors and Free Radicals in Health and Disease  2003.12 

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    Venue：Kyoto  

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  • 尿酸及びエダラボンを規範とした抗酸化剤のプロオキシダント効果の検討.

    田中悠貴, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第131年会  2011.3 

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    Venue：静岡  

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  • α-pyridoin誘導体の抗酸化活性における置換基効果.

    畑中雅史, 高橋恭子, 増野匡彦

    第25回日本フリーラジカル学会  2003.6 

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    Venue：東京  

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  • Anti-proliferative activities on cancer cell by cationic fullerene derivatives. International conference

    ○Nakamura S, Yokoo S, Kondo S, Koizumi Y, Takahashi K, Mashino T

    The 2010 International Chemical Congress of Pacific Basin Societies  2010.12 

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    Venue：Honolulu, USA  

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  • Peroxinitrite Scavenging Activity of Antioxidative Synthetic Uric Acid Analogs. International conference

    ○Takahashi K, Ito M, Yasuda D, Nakamura S, Mashino T

    International Symposium on Free Radical Research: Contribution to Medicine  2011.1 

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    Venue：Kyoto  

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  • Antibacterial activity of cationic fullerene derivatives. International conference

    Nishikawa D, Ikegami N, Takahashi K, Endo T, Mochizuki M, Mashino T

    5th Asian Federation for Medicinal Chemistry,  2003.10 

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    Venue：Kyoto, Japan  

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  • 環境ホルモン、ノニルフェノールの新規代謝物、4-hydroxynonanophenone、hydroquinoneの生成とエストロゲン受容体結合能.

    手塚淑人, 高橋恭子, 鈴木智晴, 太田茂, 増野匡彦

    日本薬学会第124年会  2004.3 

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    Venue：大阪  

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  • HIV 逆転写酵素阻害活性を有する二置換型フラーレン誘導体の合成.

    篠原舞, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第131年会  2011.3 

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    Venue：静岡  

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  • ピロリジン環を有するC60誘導体の抗菌活性.

    西川大, 池上典子, 高橋恭子, 関昌子, 遠藤豊成, 望月正隆, 増野匡彦

    日本薬学会第124年会  2004.3 

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    Venue：大阪  

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  • α-Pyridoin 誘導体の抗酸化活性と金属イオン介在プロオキシダント効果.

    畑中雅史, 高橋恭子, 増野匡彦

    日本薬学会第124年会  2004.3 

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    Venue：大阪  

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  • 尿酸類縁体の活性窒素種消去活性.

    伊藤舞, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第131年会  2011.3 

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    Venue：静岡  

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  • 抗HCV活性を有するスルホンアミド型フラーレン誘導体のデザインと合成.

    田丸友裕, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第131年会  2011.3 

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    Venue：静岡  

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  • 新規エンジオール系抗酸化剤の開発.

    畑中雅史, 高橋恭子, 増野匡彦

    第23回メディシナルケミストリーシンポジウム・第12回日本薬学会医薬化学部会年会  2004.10 

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    Venue：つくば  

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  • インダノン誘導体の一重項酸素消去活性と光障害保護効果.

    前田和貴子, 幸田愛未, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第131年会  2011.3 

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    Venue：静岡  

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  • alpha-Pyridoin とアスコルビン酸のプロオキシダント効果.

    畑中雅史, 高橋恭子, 増野匡彦

    第43回電子スピンサイエンス学会年会  2004.10 

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    Venue：東京  

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  • 置換phenacyl基を有する5-hydroxyoxindole誘導体のラジカル消去活性とXO阻害活性.

    安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    第64回日本酸化ストレス学会学術集会  2011.7 

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    Venue：北海道  

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  • beta-Diketone誘導体のラジカル消去活性.

    齋藤亮, 松井裕信, 高橋恭子, 増野匡彦

    日本薬学会第124年会  2004.3 

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    Venue：大阪  

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  • Diethylstilbestrolのipso位P450代謝反応に及ぼす構造因子の解析.

    川島千明, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第131年会  2011.3 

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    Venue：静岡  

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  • alpha-Pyridoin 誘導体のラジカル消去活性と脂質過酸化抑制効果.

    畑中雅史, 高橋恭子, 増野匡彦

    第26回日本フリーラジカル学会学術集会  2004.6 

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    Venue：山形  

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  • 尿酸類縁体の抗酸化活性とキサンチンオキシダーゼ阻害活性; 五員環部位の構造変換.

    安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第131年会  2011.3 

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    Venue：静岡  

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  • 1-Methoxycarbonyl-2-indanone scavenged sinflet oxigen and protected against UV-induned cell damage. International conference

    ○Takahashi K, Maeda W, Koda A, Nakamura S, Mashino T

    5th Biennial Meeting of Society for Free Radical Research-Asia(SFRR-Asia)  2011.8 

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    Venue：Kagoshima  

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  • Human Immunodeficiency Virus-Reverse Transcriptase and Hepatitis C Virus RNA-Dependent RNA Polymerase Inhibition Activities of Fullerene Derivatives. International conference

    ○Mashino T, Shimotohno K, Ikegami N, Nishikawa D, Takahashi K, Nakamura S, Mochizuki M

    206th Electrochemical Society Meeting  2004.10 

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    Venue：Honolulu, Hawaii  

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  • 新規エンジオール系抗酸化剤の開発.

    畑中雅史, 高橋恭子, 増野匡彦

    第23回メディシナルケミストリーシンポジウム・第12回日本薬学会医薬化学部会年会  2004.11 

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    Venue：つくば  

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  • Developing of Novel Antioxidant Based on a Structure of Uric Acid, Potent Endogenous Antioxidant. International conference

    Yasuda D, Tanaka Y, Kakinoki T, Takahashi K, Nakamura S, Mashino T

    8th AFMC International Medicinal Chemistry Symposium  2011.11 

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    Venue：Tokyo, Japan  

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  • 1,3-Cyclopentanedione骨格を有する抗酸化剤の開発.

    齋藤亮, 高橋恭子, 増野匡彦

    第48回日本薬学会関東支部大会  2004.10 

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    Venue：千葉  

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  • アスコルビン酸のプロオキシダント効果に対するフラーレン誘導体の抑制効果.

    宮川知美, 高橋恭子, 中村成夫, 増野匡彦

    第55回日本薬学会関東支部大会  2011.8 

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    Venue：千葉  

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  • フラーレン誘導体のHIV逆転写酵素阻害活性.

    池上典子, 高橋恭子, 中村成夫, 下遠野久美子, 西川大, 望月正隆, 増野匡彦

    第48回日本薬学会関東支部大会  2004.10 

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    Venue：千葉  

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  • 尿酸アナログの抗酸化活性と構造活性相関-2.

    田中陽子, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    第55回日本薬学会関東支部大会  2011.8 

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    Venue：千葉  

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  • 中性条件での環状βージケトン化合物の抗酸化活性.

    寺井栄一郎, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第127年会  2007.3 

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    Venue：富山  

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  • 蛍光標識化フラーレン誘導体の創製.

    亀山実佳子, 小川香菜子, 丸山しおり, 安田大輔, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第134年会  2014.3 

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    Venue：熊本  

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  • Bisacodyl のラット肝ミクロソーム系での代謝と ipso 位置換反応による新規代謝物の検討.

    土門周, 久保田晃代, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第127年会  2007.3 

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    Venue：富山  

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  • Radical scavenging and lipid peroxidation suppressive activity of 3-pyridinylinden-2-ols. International conference

    ○Fujita R, Maruyama K, Takahashi K, Ohe T, Nakamura S, Mashino T

    17th Biennial Meeting of Society for Free Radical Research International  2014.3 

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    Venue：Kyoto  

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  • 抗HIV及び抗がん活性を有する新規ピリジニウム型フラーレン誘導体の創製.

    安野拓実, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第134年会  2014.3 

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    Venue：熊本  

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  • 少人数グループ学習による「ヒューマニティー・コミュニケーション教育」その2.

    阿部芳廣, 飯島史朗, 石川さと子, 江原吉博, 後藤恵子, 小林静子, 重野豊隆, 高橋恭子, 藤本和子, 福島紀子

    日本薬学会 第127年会  2007.3 

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    Venue：富山  

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  • ヒューマニティ教育の基盤となるための「プレゼンテーション」と「情報科学」.

    石川さと子, 小林静子, 阿部芳廣, 江原吉博, 重野豊隆, 高橋恭子, 福島紀子, 藤本和子, 後藤惠子, 飯島史朗

    日本薬学会 第127年会  2007.3 

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    Venue：富山  

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  • ラベタロールの代謝活性化機構の解析.

    中村文子, 櫻井美希, 北川原弓奈, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第134年会  2014.3 

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    Venue：熊本  

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  • HIV関連疾患治療薬を目指した多標的型フラーレン誘導体の開発.

    大江知之, 片岡裕樹, 安野拓実, 秋葉智紘, 篠原舞, 高橋恭子, 中村成夫, 増野匡彦

    第1回ナノカーボンバイオシンポジウム  2014.9 

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    Venue：名古屋  

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  • 細胞系における 2,2'-pyridil の酸化ストレス防御効果.

    畑中雅史, 西澤千穂, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第127年会  2007.3 

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    Venue：富山  

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  • 3-Heteroaryl-2-indenol 型新規抗酸化剤の創製

    FUJITA Ryosuke, TAKAHASHI Kyoko, NAKAMURA Shigeo, OHE Tomoyuki, MASHINO Tadahiko

    第 29 回日本酸化ストレス学会関東支部会  2014.12  日本酸化ストレス学会関東支部会

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    Venue：東京  

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  • がん細胞増殖抑制効果を有するカチオン型フラーレン誘導体による細胞内酸化ストレスの惹起.

    西澤千穂, 橋本規行, 森裕美子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第127年会  2007.3 

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    Venue：富山  

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  • 抗酸化活性尿酸アナログのラット胸腺細胞を用いた放射線防護活性評価.

    関根(鈴木, 絵美子, 小川幸大, 安田大輔, 高橋恭子, 中西郁夫, 上野恵美, 松本謙一郎, 安西和紀, 増野匡彦, 村上健

    第67回日本酸化ストレス学会学術集会  2014.9 

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    Venue：京都  

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  • がん細胞増殖抑制効果を持つカチオン型フラーレン誘導体のアポトーシス誘導.

    橋本規行, 西澤千穂, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第127年会  2007.3 

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    Venue：富山  

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  • HIV逆転写酵素阻害活性を有する新規フラーレン誘導体のデザインと合成.

    秋保裕子, 横尾祥子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第127年会  2007.3 

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    Venue：富山  

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  • ラジカル消去活性を有する新規環状ジペプチドアナログの創製.

    高橋恭子, 槇田智史, 池貴幸, 沼館慧剛, 大江知之, 中村成夫, 増野匡彦

    第67回日本酸化ストレス学会学術集会  2014.9 

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    Venue：京都  

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  • Generation of Reactive Oxygen Species by Antiproliferative Fullerene Derivative. International conference

    ○Nishizawa C, Hashimoto N, Takahashi K, Nakamura S, Mashino T

    211th Meeting of The Electrochemical Society  2007.5 

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    Venue：Chicago, USA  

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  • Antioxidant Activity of Fullerene Derivative Lacking Prooxidant Activity. International conference

    Nakamura S, Satake E, Hatanaka M, Takahashi K, Mashino T

    211th Meeting of The Electrochemical Society  2007.5 

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    Venue：Chicago, USA  

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  • 多標的型AIDS関連疾患治療薬を目指した5-(methylpyridinium)proline 型フラーレン誘導体の構造変環

    YASUNO Takumi, TAKAHASHI Kyoko, NAKAMURA Shigeo, OHE Tomoyuki, MASHINO Tadahiko

    日本薬学会第135年会  2015.3  日本薬学会

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    Venue：東京  

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  • 2,2'-Pyridoin 類縁体の細胞系における酸化ストレス抑制効果と水溶液中における安定性の検討.

    畑中雅史, 西澤千穂, 高橋恭子, 中村成夫, 増野匡彦

    第29回日本フリーラジカル学会学術集会 日本過酸化脂質・フリーラジカル学会第31回大会  2007.6 

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    Venue：名古屋  

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  • HCV RNAポリメラーゼ阻害活性を有する新規プロリン型フラーレン誘導体の創製

    KATAOKA Hiroki, TAKAHASHI Kyoko, NAKAMURA Shigeo, OHE Tomoyuki, MASHINO Tadahiko

    日本薬学会第135年会  2015.3  日本薬学会

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    Venue：東京  

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  • "チオラクタム構造を経由した新規水溶性フラーレン誘導体の合成とその脂質過酸化抑制効果"

    OMOTO Takashi, TAKAHASHI Kyoko, NAKAMURA Shigeo, OHE Tomoyuki, MASHINO Tadahiko

    日本薬学会第135年会  2015.3  日本薬学会

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    Venue：東京  

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  • プロリン型フラーレン誘導体の立体異性体の合成とHIV逆転写酵素阻害活性.

    秋保裕子, 竹内由紀, 高橋恭子, 中村成夫, 増野匡彦

    第51回日本薬学会関東支部大会  2007.10 

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    Venue：東京  

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  • 抗酸化活性環状ジペプチド化合物の脂質過酸化抑制効果

    MAKITA Satoshi, TAKAHASHI Kyoko, IKE Takayuki, YASUDA Daisuke, NAKAMURA Shigeo, OHE Tomoyuki, MASHINO Tadahiko

    第68回日本酸化ストレス学会学術集会  2015.6  日本酸化ストレス学会

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    Venue：鹿児島  

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  • インドール共役ヒダントイン誘導体の合成とラジカル消去活性

    OKAZAKI Nozomi, MAKITA Satoshi, TAKAHASHI Kyoko, OHE Tomoyuki, NAKAMURA Shigeo, MASHINO Tadahiko

    第５９回日本薬学会関東支部大会  2015.9  日本薬学会関東支部

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    Venue：船橋  

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  • 抗HCV活性を有する新規フラーレン誘導体.

    中村成夫, 笠原優子, 深澤征義, 森裕美子, 高橋恭子, 下遠野久美子, 増野匡彦

    第26回メディシナルケミストリーシンポジウム  2007.11 

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    Venue：相模原  

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  • C-4位メチル基が関与するnevirpineの代謝活性化機構の解析

    TOMOEGAWA Yoko, TAKAHASHI Kyoko, NAKAMURA Shigeo, OHE Tomoyuki, MASHINO Tadahiko

    日本薬学会第135年会  2015.3  日本薬学会

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    Venue：東京  

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  • がん細胞におけるカチオン型フラーレン誘導体によるアポトーシスの誘導と活性酸素の生成.

    西澤千穂, 橋本規行, 高橋恭子, 中村成夫, 増野匡彦

    第29回日本フリーラジカル学会学術集会 日本過酸化脂質・フリーラジカル学会第31回大会  2007.6 

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    Venue：名古屋  

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  • 新規抗酸化剤環状 arylvinyl alcohol 類のデザインと合成

    FUJITA Ryosuke, TAKAHASHI Kyoko, YASUDA Daisuke, NAKAMURA Shigeo, OHE Tomoyuki, MASHINO Tadahiko

    日本薬学会第135年会  2015.3  日本薬学会

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    Venue：東京  

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  • Bisacodyl の新規代謝様式 ipso 位置換に関与するヒト P450 分子種の探索.

    土門周, 高橋恭子, 中村成夫, 増野匡彦

    第51回日本薬学会関東支部大会  2007.10 

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    Venue：東京  

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  • 多職種医療系学生交流合同セミナー -インタープロフェッショナル教育の試み-.

    小林静子, 江原吉博, 阿部芳廣, 福島紀子, 望月眞弓, 重野豊隆, 飯島史朗, 石川さと子, 高橋恭子, 後藤惠子

    日本薬学会第128年会  2008.3 

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    Venue：横浜  

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  • Synthesis of multi-target fullerene derivatives with both HCV RNA polymerase inhibitory and antioxidant activities for the treatment of HCV-related disease. International conference

    KATAOKA Hiroki, TAKAHASHI Kyoko, OHE Tomoyuki, NAKAMURA Shigeo, MASHINO Tadahiko

    THE INTERNATIONAL CHEMICAL CONGRESS OF PACIFIC BASIN SOCIETIES 2015  2015.12  American Chemical Society

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    Venue：Honolulu, USA  

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  • 尿酸類縁体の抗酸化活性における構造活性相関.

    柿木智宏, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第128年会  2008.3 

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    Venue：横浜  

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  • 尿酸の抗酸化活性発現部位の決定.

    柿木智宏, 松本麻里子, 横川めぐみ, 高橋恭子, 中村成夫, 増野匡彦

    第22回日本酸化ストレス学会関東支部会  2007.12 

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    Venue：東京  

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  • 尿酸の構造を単純化した 置換インドリノン誘導体の合成と抗酸化活性

    TAKAHASHI Kyoko, IGARASHII Taku, HIRAISHI Itaru, OHE Tomoyuki, NAKAMURA Shigeo, MASHINO Tadahiko

    第33回メディシナルケミストリーシンポジウム  2015.11  日本薬学会医薬化学部会

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    Venue：幕張  

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  • Novel bioactivation pathway of benzbromarone mediated by cytochrome P450

    OHE Tomoyuki, KITAGAWARAYumina, TACHIBANA Kumiko, TAKAHASHI Kyoko, NAKAMURA Shigeo, MASHINO Tadahiko

    日本薬物動態学会第30回年会  2015.11  日本薬学会医薬化学部会

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    Venue：幕張  

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  • Radical Scavenging Activity and Cell Protection Activity against Oxidative Stress of 2,2'-Pyridoin and Its Related Compounds. International conference

    Nakamura S, Hatanaka M, Nishizawa C, Takahashi K, Mashino T

    4th Joint Meeting of the Society for Free Radical Research Australasia and Japan  2007.12 

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    Venue：Kyoto, Japan  

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  • 5位に芳香環を有するプロリン型フラーレン誘導体のHIV逆転写酵素阻害活性.

    秋保裕子, 竹内由紀, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第128年会  2008.3 

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    Venue：横浜  

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  • アルツハイマー病酸化ストレス仮説に基づいた2-インダノン誘導体の活性評価

    平井 翔子, 藤田 亮輔, 高橋 恭子, 中村 成夫, 大江 知之, 増野 匡彦

    第30回日本酸化ストレス学会関東支部会  2015.12  日本酸化ストレス学会関東支部

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    Venue：東京  

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  • 肝毒性を示す医薬品の代謝活性化機構の解析とそれに基づいた創薬戦略

    大江 知之, 高橋 恭子, 中村 成夫, 増野 匡彦

    日本薬学会第136年会  2016.3  日本薬学会

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    Venue：横浜  

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  • 抗HCV薬を目指したスルホニウム置換基を有するフラーレン誘導体の合成.

    森裕美子, 下遠野久美子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第128年会  2008.3 

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    Venue：横浜  

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  • 2位側鎖にエステル基を有するピロリジニウム型フラーレン誘導体のアポトーシス誘導効果の検討.

    小泉由起, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • インドールを有する環状 ジペプチドの ONOO- 消去活性.

    田中彩夏, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第56回日本薬学会関東支部大会  2012.10 

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    Venue：東京  

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  • 1,2-Di-(2-pyridyl)ethanone誘導体のラジカル消去活性.

    丸山和輝, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第133年会  2013.3 

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    Venue：横浜  

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  • フラーレン誘導体によるCu2+/アスコルビン酸誘発DNA切断の抑制.

    古田恭寛, 元井玲子, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第133年会  2013.3 

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    Venue：横浜  

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  • ラジカル種/ONOO-消去ハイブリッド型抗酸化剤の創製.

    高橋恭子, 伊藤舞, 古藤有理, 田中彩夏, 大江知之, 中村成夫, 増野匡彦

    第27回日本酸化ストレス学会関東支部  2012.12 

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    Venue：東京  

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  • フラーレン誘導体添加による抗酸化剤プロオキシダント効果の抑制.

    宮川知美, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第26回日本酸化ストレス学会関東支部学術大会  2012.12 

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    Venue：東京  

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  • ベンズブロマロンの新規代謝物の探索とその肝毒性との関連.

    北川原弓奈, 橘久美子, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第133年会  2013.3 

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    Venue：横浜  

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  • α-Pyridoin 誘導体の一重項酸素消去活性.

    松藤舞, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第133年会  2013.3 

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    Venue：横浜  

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  • 新規抗酸化剤β-ケトエステル型インドール誘導体の創製.

    藤田亮輔, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第66回日本酸化ストレス学会学術集会  2013.6 

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    Venue：名古屋  

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  • 抗HCV薬を目指した立体異性体のないフラーレン誘導体のデザインと合成.

    片岡裕樹, 黒須寛貴, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第57回日本薬学会関東支部大会  2013.10 

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    Venue：東京  

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  • Development of 3,5-dihydroxy-2-oxindoles as novel antioxidant for lipid peroxidation and intracellular oxidative stress. International conference

    ○Yasuda D, Takahashi K, Ohe T, Nakamura S, Mashino T

    6th Biennial Meeting of Society for Free Radical Research-Asia(SFRR-Asia)  2013.10 

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    Venue：Linkou, Taiwang  

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  • アルキル置換フェナシル基を有する5-ヒドロキシオキシインドール誘導体のH2O2誘発細胞死に対する細胞保護効果.

    安田大輔, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第66回日本酸化ストレス学会学術集会  2013.10 

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    Venue：名古屋  

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  • 抗HIV・抗がん活性を有する新規二置換型フラーレン誘導体の創製.

    安野拓実, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第57回日本薬学会関東支部大会  2013.10 

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    Venue：東京  

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  • 新規環状ジペプチド誘導体のラジカル消去活性.

    池貴幸, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第134年会  2014.3 

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    Venue：熊本  

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  • 5-ヒドロキシオキシインドール誘導体の細胞内酸化ストレス抑制効果.

    安田大輔, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第134年会  2014.3 

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    Venue：熊本  

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  • 肝毒性を示す医薬品の代謝的活性化を回避した創薬アプローチ:ベンズブロマロンおよび ラベタロールの新規反応性代謝物の同定と肝毒性との関連.

    大江知之, 北川原弓奈, 中村文子, 橘久美子, 高橋恭子, 中村成夫, 増野匡彦

    第31回メディシナルケミストリーシンポジウム  2013.11 

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    Venue：広島  

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  • 抗HIV薬を目指したピリジン側鎖を有する新規プロリン型フラーレン誘導体の創製.

    安野拓実, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第31回メディシナルケミストリーシンポジウム  2013.11 

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    Venue：広島  

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  • 抗パーキンソン病作用を有する新規オキシカム系化合物の合成.

    海東和麻, 坂口智己, 小野尚志, 高橋恭子, 大江知之, 中村成夫, 田崎嘉一, 増野匡彦

    日本薬学会第134年会  2014.3 

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    Venue：熊本  

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  • 2-Pyridinylvinylalcohol 型抗酸化剤のデザイン・合成.

    藤田亮輔, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第134年会  2014.3 

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    Venue：熊本  

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  • Fullerene derivatives have antioxidant activity but no metal-dependent prooxidant activity.

    中村成夫, 佐竹恵理子, 畑中雅史, 高橋恭子, 松林賢司, 増野匡彦

    第32回フラーレン・ナノチューブ総合シンポジウム  2007.2 

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    Venue：名古屋  

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  • HCV RNAポリメラーゼ阻害活性と抗酸化活性を有するフラーレン誘導体の創製.

    片岡裕樹, 秋葉智紘, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第134年会  2014.3 

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    Venue：熊本  

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  • Antibacterial activity of C60-(N,N-dimethylpyrrolidinium iodide)derivatives.

    Nishikawa D, Takahashi K, ○Nakamura S, Endo T, Mochizuki M, Mashino T

    The 28th Fullerene-Nanotubes General Symposium  2005.1 

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    Venue：名古屋  

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  • Inhibition of HIV-Reverse Transcriptase by Amino Acid-type Fullerene Derivatives and Effect of Substituent on Pyrrolidine Ring. International conference

    Nakamura S, Takeuchi Y, Shinohara M, Takahashi K, Mashino T

    8th AFMC International Medicinal Chemistry Symposium  2011.11 

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    Venue：Tokyo  

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  • Human immunodeficiency virus-reverse transcriptase inhibition activities of fullerene derivatives.

    ○Ikegami N, Shimotohno K, Nishikawa D, Takahashi K, Nakamura S, Mochizuki M, Mashino T

    The 28th Fullerene-Nanotubes General Symposium  2005.1 

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    Venue：名古屋  

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  • フラーレン誘導体添加による抗酸化剤プロオキシダント効果の抑制.

    宮川知美, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第26回日本酸化ストレス学会関東支部学術大会  2011.12 

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    Venue：東京  

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  • 1,3-Cyclopentanedione誘導体の抗酸化活性に対する置換基効果.

    齋藤亮, 高橋恭子, 増野匡彦

    日本薬学会第125年会  2005.3 

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    Venue：東京  

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  • シトクロムP450によるipso位代謝反応の医薬品への応用研究.

    大江知之, 清水香往, 土門周, 高橋恭子, 中村成夫, 増野匡彦

    第15回生体触媒化学シンポジウム  2011.12 

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    Venue：東京  

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  • HCV-RNA ポリメラーゼ及び HIV 逆転写酵素阻害活性を有する新規フラーレン誘導体の合成.

    篠原舞, 高橋恭子, 大江知之, 中村成夫, 下遠野久美子, 増野匡彦

    日本薬学会第132年会  2012.3 

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    Venue：札幌  

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  • ipso置換によるsalbutamolの新規代謝物の探索.

    清水香住, 杉浦なつき, 手塚淑人, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第125年会  2005.3 

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    Venue：東京  

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  • 薬学教育におけるチュートリアルの試み.

    阿部芳廣, 下遠野久美子, 鈴木岳之, 飯島史朗, 藤本和子, 服部研之, 石川さと子, 高橋恭子, 松本佳代子, 村上勳, 小林静子

    日本薬学会  2005.3 

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    Venue：東京  

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  • 抗酸化活性を有する環状ジペプチド誘導体の創製.

    沼館慧剛, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第132年会  2012.3 

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    Venue：札幌  

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  • 抗酸化能を有するalpha-pyridoin類縁体の活性構造.

    畑中雅史, 寺井栄一郎, 高橋恭子, 増野匡彦

    日本薬学会第125年会  2005.3 

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    Venue：東京  

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  • フラーレン結合型シリカゲル担体の合成.

    井田遙, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第132年会  2012.3 

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    Venue：札幌  

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  • シトクロムP450によるビスフェノールＡのipso置換型新規代謝物ヒドロキノンの生成.

    手塚淑人, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第125年会  2005.3 

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    Venue：東京  

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  • 3位置換Oxindole誘導体のXanthine Oxidase阻害活性と構造活性相関.

    安田大輔, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    日本薬学会第132年会  2012.3 

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    Venue：札幌  

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  • 脂溶性を向上した5-Hydroxy-2-oxindole誘導体の抗酸化活性.

    安田大輔, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第65回日本酸化ストレス学会学術集会  2012.6 

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    Venue：徳島  

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  • alpha-Arylcyclopentanone 骨格を有する抗酸化剤のデザイン・合成と活性評価.

    寺井 栄一郎, 齋藤 亮, 松澤 咲世, 高橋 恭子, 中村 成夫, 増野 匡彦

    第49回日本薬学会関東支部大会  2005.10 

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    Venue：東京  

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  • Cytochrome P450 による ipso 置換型代謝物の検索 _ Salbutamol からの colterol の生成.

    清水香住, 手塚淑人, 高橋恭子, 中村成夫, 増野匡彦

    第49回日本薬学会関東支部大会  2005.10 

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    Venue：東京  

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  • Methoxycarbonyl-2-indanone and its derivatives as bifunctional radicals/ singlet oxygen- scavengers; cytoprotective effect against UV-irradiation. International conference

    ○Takahashi K, Maeda W, Koda K, Ohe T, Nakamura S, Mashino T

    16th SFRRI Biennial Meeting  2012.9 

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    Venue：London, UK.  

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  • フルバスタチン構造を基にした新規抗酸化化合物の創製.

    関陽平, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第132年会  2012.3 

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    Venue：札幌  

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  • 1,3−ジカルボニル化合物の抗酸化活性.

    齋藤 亮, 寺井栄一郎, 高橋恭子, 増野匡彦

    第27会日本フリーラジカル学会学術集会  2005.6 

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    Venue：岡山  

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  • 抗HCV活性を有するフラーレン誘導体における抗酸化活性.

    片岡裕樹, 田丸友裕, 下遠野久美子, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第65回日本酸化ストレス学会学術集会  2012.6 

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    Venue：徳島  

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  • 白金ナノ粒子の細胞死抑制.

    渡邊亜紀, 梶田昌志, 高橋恭子, 増野匡彦, 久恒辰博, 宮本有正

    第58回コロイドおよび界面化学討論会  2005.9 

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    Venue：宇都宮  

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  • 内分泌攪乱物質ビスフェノールAのシトクロムP450による新規開裂反応およびその生成物のエストロゲン様活性.

    手塚淑人, 高橋恭子, 中村成夫, 太田茂, 増野匡彦

    フォーラム2005衛生薬学・環境トキシコロジー  2005.10 

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    Venue：徳島  

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  • シトクロムP450化学モデルおよびシトクロムP450による環境エストロゲンの酸化.

    増野匡彦, 手塚淑人, 高橋恭子, 中村成夫

    第38回酸化反応討論会  2005.11 

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    Venue：札幌  

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  • 2,2'-Thenoin類縁体の抗酸化活性.

    畑中雅史, 寺井栄一郎, 高橋恭子, 中村成夫, 増野匡彦

    第24回メディシナルケミストリーシンポジウム  2005.11 

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    Venue：大阪  

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  • Novel metabolites of bisphenol A catalyzed by cytochrome P450 and its chemical model system. International conference

    ○Tezuka Y, Takahashi K, Nakamura S, Mashino T

    International Chemical Congress of Pacific Basin Societies2005  2005.12 

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    Venue：Honolulu, USA  

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  • Antioxidant activity of 1,3-dicarbonyl compounds. International conference

    Saito M, ○Takahashi K, Terai E, Nakamura S, Mashino T

    International Chemical Congress of Pacific Basin Societies2005  2005.12 

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    Venue：Honolulu, USA  

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  • Thenoin 誘導体の抗酸化活性とプロオキシダント効果.

    畑中雅史, 高橋恭子, 中村成夫, 増野匡彦

    第20回日本フリーラジカル学会関東支部会  2005.12 

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    Venue：東京  

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  • Antioxidant activity of alpha-pyridoins. International conference

    Hatanaka M, Takahashi K, Nakamura S, Mashino T

    International Chemical Congress of Pacific Basin Societies2005  2005.12 

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    Venue：Honolulu, USA  

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  • 2,2'-Thenoin誘導体の抗酸化活性とプロオキシダント効果.

    畑中雅史, 寺井栄一郎, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第126年会  2006.3 

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    Venue：仙台  

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  • Cytochrome P450 による ipso 置換型代謝物の検索 _ Salbutamol からの colterol の生成 _ .

    清水香住, 手塚淑人, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第126年会  2006.3 

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    Venue：仙台  

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  • Inhibition of HIV-reverse transcriptase by mono- or bis-substituted fullerene derivatives. International conference

    Ikegami N, Shimotohno K, Nishikawa D, Takahashi K, ○Nakamura S, Mochizuki M, Mashino T

    International Chemical Congress of Pacific Basin Societies2005  2005.12 

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    Venue：Honolulu, USA  

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  • 少人数グループ学習による「ヒューマニティー・コミュニケ＾ション教育」.

    小林静子, 阿部芳廣, 飯島史朗, 石川さと子, 江原吉博, 後藤恵子, 重野豊隆, 高橋恭子, 福島紀子, 藤本和子

    日本薬学会  2006.3 

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    Venue：仙台  

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  • シトクロムP450によるビスフェノール類の新規代謝反応およびその反応機構検討.

    手塚淑人, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第126年会  2006.3 

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    Venue：仙台  

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  • C60プロリン誘導体によるHIV逆転写酵素阻害効果及びその阻害機構.

    池上典子, 高橋恭子, 中村成夫, 下遠野久美子, 望月正隆, 増野匡彦

    日本薬学会第126年会  2006.3 

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    Venue：仙台  

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  • フラーレン誘導体置換基の種類による細胞毒性発現.

    橋本規行, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第126年会  2006.3 

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    Venue：仙台  

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  • Antioxidant Activity of 2-Arylcyclopentanone Derivatives. International conference

    ○Terai E, Saito M, Takahashi K, Nakamura S, Mashino T

    7th TETRAHEDRON SYMPOSIUM  2006.5 

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    Venue：名古屋  

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  • Bisacodyl からの新規代謝物 hydroquinone 生成の検討.

    土門周, 久保田晃代, 高橋恭子, 中村成夫, 増野匡彦

    第50回日本薬学会関東支部大会  2006.10 

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    Venue：新潟  

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  • フラーレン誘導体の抗酸化作用とプロオキシダント効果の検討.

    佐竹恵理子, 高橋恭子, 中村成夫, 増野匡彦, 松林賢司

    第28回日本フリーラジカル学会学術集会  2006.5 

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    Venue：津  

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  • Human Immunodeficiency Virus-Reverse Transcriptase Inhibition and Hepatitis C Virus RNA-Dependent RNA Polymerase Inhibition Activities of Fullerene Derivatives. International conference

    Mashino T, Shimotohno K, Ikegami N, Takahashi K, ○Nakamura S, Mochizuki M

    209th Meeting of The Electrochemical Society  2006.5 

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    Venue：Denver, USA  

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  • がん細胞増殖抑制作用を有するフラーレン誘導体による細胞内活性酸素生成.

    西澤千穂, 橋本規行, 高橋恭子, 中村成夫, 増野匡彦

    第21回日本フリーラジカル学会関東支部会  2006.12 

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    Venue：東京  

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  • 抗酸化活性を有する2-Indanone 誘導体の探索.

    西野優希, 中川真弥子, 高橋恭子, 中村成夫, 増野匡彦

    第50回日本薬学会関東支部大会  2006.10 

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    Venue：新潟  

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  • 細胞培養系における 2,2'-pyridoin 類縁体の酸化ストレス抑制効果.

    畑中雅史, 高橋恭子, 中村成夫, 増野匡彦

    第25回メディシナルケミストリーシンポジウム  2006.12 

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    Venue：名古屋  

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  • Synthesis, Structure-Activity Relationship and Antioxidant Activity of Uric Acid Analogs. International conference

    ○Takahashi K, Kakinoki T, Yasuda D, Nakamura S, Mashino T

    SFRR Europe Meeting - Rome 2009  2009.8 

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    Venue：Rome, Italy  

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  • がん細胞増殖抑制効果を有するカチオン型フラーレン誘導体による活性酸素産生およびその構造活性相関

    池田瞳, 安田大輔, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    第62回日本薬学会関東支部大会  2018.9  第62回日本薬学会関東支部大会

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    Venue：東京  

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  • 新規アザフレロイド誘導体の合成と HCV RNA ポリメラーゼ阻害活性

    藪内大貴, 片岡裕樹, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    第62回日本薬学会関東支部大会  2018.9  第62回日本薬学会関東支部大会

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    Venue：東京  

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  • HIV-Reverse Transcriptase Inhibitory Activities of Proline-Type Fullerene Derivatives Containing Hydrophobic Substituents on Pyrrolidine Ring. Invited International conference

    Nakamura S, Takeuchi Y, Takahashi K, Mashino T

    The 13th Asian Chemical Congress  2009.9 

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    Venue：Shanghai, China  

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  • ピロリジニウム型フラーレン誘導体の細胞内酸化ストレス惹起と抗酸化剤の効果.

    横尾祥子, 高橋恭子, 中村成夫, 増野匡彦

    第62回日本酸化ストレス学会学術集会  2009.6 

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    Venue：福岡  

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  • 抗酸化活性を有する非フェノール型尿酸アナログの創製

    伊藤理人, 比留川史也, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第138年会  2018.3  日本薬学会第138年会

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    Venue：仙台  

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  • 抗がん剤耐性克服を志向したKeap1-リン酸化p62タンパク質間相互作用阻害剤の創薬研究

    安田大輔, 中島真央, 髙橋恭子, 大江知之, 一村義信, 小松雅明, 今村理世, 小島宏建, 岡部隆義, 長野哲雄, 増野匡彦

    第71回日本酸化ストレス学会  2018.5  第71回日本酸化ストレス学会

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    Venue：京都  

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  • ヒドロキノン等価構造を有する尿酸誘導体のデザインと抗酸化活性.

    安田大輔, 柿木智宏, 高橋恭子, 中村成夫, 増野匡彦

    第62回日本酸化ストレス学会学術集会  2009.6 

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    Venue：福岡  

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  • フラーレン誘導体によるTNFα誘導性NFκB 活性化の抑制.

    井上巧, 伊藤雅之, 山名修一, 高橋恭子, 中村成夫, 増野匡彦

    第37回フラーレン・ナノチューブ総合シンポジウム  2009.9 

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    Venue：つくば  

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  • フッ素導入により反応性代謝物の生成を回避した改良型Diclofenac類縁体の創製

    小川 真依, 山田晶子, 安田大輔, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第139年会  2019.3  日本薬学会第139年会

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    Venue：千葉  

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  • シトクロムP450によるp-置換フェノールのNIH転位とipso代謝反応の関連性.

    榎本千聡, 高橋恭子, 中村成夫, 増野匡彦

    第53回日本薬学会関東支部大会  2009.10 

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    Venue：埼玉  

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  • 抗パーキンソン病活性を有するテトラロンアナログB環へのフッ素の導入と神経細胞保護効果

    伊藤廉, 梅本英明, 三山由茉子, 高橋恭子, 中村成夫, 大江知之, 大久保知子, 春名柚佳, 田﨑嘉一, 増野匡彦

    日本薬学会第139年会  2019.3  日本薬学会第139年会

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    Venue：千葉  

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  • 共役ケトンを有するステロイドのがん細胞増殖抑制効果.

    小川広志, 高橋恭子, 中村成夫, 増野匡彦

    第53回日本薬学会関東支部大会  2009.10 

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    Venue：埼玉  

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  • p62-Keap1-Nrf2系を標的としたPPI阻害剤の幹細胞がん薬剤耐性抑制効果

    安田大輔, 大江知之, 高橋恭子, 小松雅明, 一村義信, 山本雅之, 今村理世, 小島宏建, 岡部隆義, 長野哲雄, 増野匡彦

    第36回メディシナルケミストリーシンポジウム  2018.11  第62回日本薬学会関東支部大会

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    Venue：東京  

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  • 6-Phenacyl-3-pyridinolを基本骨格とする新規抗酸化剤.

    畑中雅史, 高橋恭子, 中村成夫, 増野匡彦

    第24回日本酸化ストレス学会関東支部会  2010.1 

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    Venue：大阪  

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  • オキシカム構造を模倣したスルホン類の抗パーキンソン病効果

    小町元輝, 鈴木啓太, 高橋恭子, 中村成夫, 大江知之, 大久保知子, 春名柚佳, 田﨑嘉一, 増野匡彦

    日本薬学会第139年会  2019.3  日本薬学会第139年会

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    Venue：千葉  

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  • ハード及びソフトな反応性代謝物を捕捉する新規蛍光標識トラッピング剤の創製

    柴崎智香子, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第139年会  2019.3  日本薬学会第139年会

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    Venue：千葉  

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  • トリフェニルエチレン誘導体のコレステロール生合成に及ぼす影響.

    高橋恭子, 伊藤崇裕, 篠原聡子, 森崎益雄

    日本薬学会 第121年会  2001.3 

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    Venue：札幌  

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  • カチオン性フラーレン誘導体の細胞内酸化ストレス惹起効果及びがん細胞増殖抑制効果.

    近藤祥子, 高橋恭子, 中村成夫, 増野匡彦

    第24回日本酸化ストレス学会関東支部会  2010.1 

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    Venue：大阪  

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  • 新規尿酸アナログの抗酸化活性とキサンチンオキシダーゼ阻害活性.

    安田大輔, 柿木智宏, 高橋恭子, 中村成夫, 増野匡彦

    第28回メディシナルケミストリーシンポジウム  2009.11 

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    Venue：東京  

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  • HIVプロテアーゼおよび逆転写酵素阻害活性を有する新規多標的型C60誘導体の創製：基質遷移状態模倣型イソスターとC60コアを結ぶリンカーの長さの検討

    古川 慶吾, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第139年会  2019.3  日本薬学会第139年会

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    Venue：千葉  

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  • ハードな反応性代謝物を捕捉する新規蛍光標識化トラッピング剤の創製

    長邑花, 柴崎智香子, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第139年会  2019.3  日本薬学会第139年会

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    Venue：千葉  

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  • HCV-RNAポリメラーゼ阻害活性を有するスルホンアミド型フラーレン誘導体.

    田丸友裕, 森裕美子, 笠原優子, 深澤征義, 下遠野久美子, 高橋恭子, 中村成夫, 増野匡彦

    創薬懇話会2009  2009.12 

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    Venue：岐阜  

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  • [24-13C, 24-2H]デスモステロール、(24R)-,および(24S)-[24-13C,24-D]コレステロールの合成.

    高橋恭子, 橋本献一郎, 藤山綾子, 森崎益雄, 藤本善徳

    日本薬学会第122年会  2002.3 

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    Venue：千葉  

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  • HCV-RNA ポリメラーゼ阻害活性を有するスルホンアミド型フラーレン誘導体の合成.

    田丸友裕, 森裕美子, 下遠野久美子, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • Ajuga毛状根におけるclionasterolの24位脱エチル化反応の機構について.

    奥住佳子, 原典行, 藤本善徳, 山田純子, 高橋恭子, 森崎益雄

    日本化学会第81春季年会  2002.3 

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    Venue：東京  

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  • ラジカル消去活性を有するインダノン誘導体の一重項酸素消去活性.

    前田和貴子, 横川めぐみ, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第130年会  2010.3 

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    Venue：岡山  

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  • Ajuga毛状根におけるステロール側鎖24位の脱エチル化反応について.

    野村佳子, 藤本善徳, 山田純子, 高橋恭子, 森崎益雄

    日本薬学会 第121年会  2001.3 

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    Venue：札幌  

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  • ピリジニウム基を有するフラーレン誘導体の合成及びがん細胞増殖抑制効果の検討.

    近藤 祥子, 高橋 恭子, 中村 成夫, 増野 匡彦

    日本薬学会第130年会  2010.3 

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    Venue：京都  

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  • 植物ステロール側鎖部の生合成機構：Δ25(27)体の24-メチルステロール生合成前駆体としての可能性.

    那須こず恵, 高橋恭子, 森崎益雄, 藤本善徳

    日本薬学会 第121年会  2001.3 

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    Venue：札幌  

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  • 5 位に脂溶性基 2 位にカルボキシル基を有するピロリジノフラーレンの合成と HIV 逆転写酵素阻害活性.

    竹内 由紀, 高橋 恭子, 中村 成夫, 増野 匡彦

    日本薬学会第130年会  2010.3 

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    Venue：京都  

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  • {[26,26,26,27,27,27-d6]-desmosterol および [26,26,26,27,27,27-d6]-cholesterol の合成.

    小林典子, 海老根明奈, 得能睦美, 高橋恭子, 森崎益雄

    日本薬学会第122年会  2002.3 

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    Venue：千葉  

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  • ステロール生合成におけるΔ24オレフィン還元反応の立体化学.

    高橋恭子, 橋本献一郎, 藤山綾子, 山田純子, 小林典子, 森崎益雄, 中村(佐藤)真子, 藤本善徳

    第44回天然有機化合物討論会  2002.10 

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    Venue：東京  

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  • Antioxidant activity of synthetic uric acid analogs. International conference

    ○Yasuda D, Ito M, Takahashi K, Ohe T, Nakamura S, Mashino T

    16th SFRRI Biennial Meeting  2012.9 

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    Venue：London, UK.  

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  • アニリニウム型フラーレン誘導体の合成及びがん細胞増殖抑制効果.

    飯田眞紀, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第56回日本薬学会関東支部大会  2012.10 

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    Venue：東京  

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  • 新規創薬テンプレートとしての抗酸化物質5-Hydroxy-2-oxindole.

    安田大輔, 高橋恭子, 大江知之, 中村成夫, 増野匡彦

    第30回メディシナルケミストリーシンポジウム  2012.11 

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    Venue：東京  

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  • 神経細胞保護効果を有する２-ヒドロキシベンゾフラン型抗酸化剤の創製

    高橋 恭子, 須貝拓馬, 安田 大輔, 中村 成夫, 大江 知之, 増野 匡彦

    第34回日本酸化ストレス学会関東支部会  2021.12 

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  • インドール類と共役したヒダントイン型およびジケトピペラジン型化合物の合成と抗酸化活性

    高橋 恭子, 宗孝典, 大江 知之, 熊谷 直哉, 中村 成夫, 増野 匡彦

    第75回日本酸化ストレス学会学術集会  2022.5 

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  • パーキンソン病治療薬を目指したオキシカムアナログIY104のADME評価および類縁体合成

    鶴岡 航太朗, 高橋 恭子, 中村 成夫, 熊谷 直哉, 増野 匡彦, 大久保 知子, 眞鍋 貴行, 田﨑 嘉一, 大江 知之

    日本薬学会第142年会  2022.3 

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  • 胆道がん治療薬を目指したフェンチコナゾール誘導体の合成と評価

    木原 和輝, 柏木 伸章, 村松 俊英, 高橋 恭子, 中村 成夫, 熊谷 直哉, 増野 匡彦, 齋藤 義正, 大江 知之

    日本薬学会第142年会  2022.3 

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  • マロン酸型フラーレン誘導体はSARS-CoV-2メインプロテアーゼを強く阻害する

    片岸 大紀, 岩﨑 彩希子, 安田 大輔, 高橋 恭子, 中村 成夫, 増野 匡彦, 熊谷 直哉, 大江 知之

    日本薬学会第142年会  2022.3 

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  • COVID-19治療薬としてのフラーレン誘導体の開発

    片岸 大紀, 安田 大輔, 高橋 恭子, 中村 成夫, 増野 匡彦, 熊谷 直哉, 大江 知之

    日本薬学会第143年会  2023.3 

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  • 代謝活性化回避を指向した新規ジクロフェナク類縁体の合成と評価

    立石泰寛, 大江知之, 小川真依, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    日本薬学会第140 年会  2020.3 

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  • HIV/HCV共感染治療薬を志向した 多標的型ピリジニウム型C60誘導体の創製

    小林透威, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    日本薬学会第140年会  2020.3 

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  • トラッピング剤を用いた反応性アシルグルクロニドの新規検出法

    柴﨑 智香子, 高橋 恭子, 中村成夫, 大江 知之, 増野 匡彦

    日本薬学会第140年会  2020.3 

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  • 抗がん活性を有するカチオン型C60誘導体のミトコンドリア機能障害

    高橋恭子, 池田瞳, 安田大輔, 中村成夫, 大江知之, 増野匡彦

    第72回日本酸化ストレス学会学術集会  2019.6 

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  • HIVプロテアーゼ/逆転写酵素、HCV NS5Bを標的とするピリジニウム型C60誘導体の創製

    小林透威, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    第64回日本薬学会関東支部大会  2010.9 

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  • グルクロン酸抱合経由の代謝活性化を回避する新規ジクロフェナク類縁体の合成と評価

    立石泰寛, 大江知之, 安田大輔, 高橋恭子, 中村成夫, 増野匡彦

    日本薬物動態学会第34回年会  2019.11 

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  • 新規反応性代謝物検出法の開発ーシステインを基盤とした蛍光標識トラッピング剤の創製とその捕捉能評価ー

    柴崎智香子, 髙橋恭子, 中村成夫, 大江知之, 増野匡彦

    第37回メディシナルケミストリーシンポジウム  2019.11 

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  • リモナバンの代謝活性化を回避する構造変換

    除川貴太, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    第63回日本薬学会関東支部大会  2019.9 

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  • HIV プロテアーゼ阻害活性を有するプロリン型フラーレン誘導体の立体選択的合成

    片岸大紀, 高橋恭子, 中村成夫, 大江知之, 増野匡彦

    第63回日本薬学会関東支部大会  2019.9 

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  • 柴﨑 智香子, 大江 知之, 高橋 恭子, 中村 成夫, 増野 匡彦

    2021.3 

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  • シトクロムP450による5-置換-2-オキシインドールのipso置換代謝反応

    公平 実希, 大江 知之, 高橋 恭子, 中村 成夫, 増野 匡彦

    日本薬学会第141年会  2021.3 

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  • 代謝活性化の回避を目指したトファシチニブ類縁体の合成と評価

    立石 泰寛, 大江 知之, 高橋 恭子, 中村 成夫, 増野 匡彦

    日本薬学会第141年会  2021.3 

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  • Stereoselective synthesis and HIV/HCV enzyme inhibition activity of proline-type fullerene derivatives

    片岸大紀, 大江知之, 高橋恭子, 中村成夫, 増野匡彦

    第59回フラーレン・ナノチューブ・グラフェン総合シンポジウム  2020.9 

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  • Stereoselective synthesis and evaluation of fullerene derivatives as antiviral drugs

    Katagishi D, Takahashi K, Nakamura S, Mashino T, Ohe T

    Pacifichem 2021  2021.12 

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  • Development of fluorescent-labeled trapping reagents based on cysteine for detecting reactive metabolites

    Shibazaki C, Takahashi K, Nakamura S, Mashino T, Ohe T

    2021.12 

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  • 抗パーキンソン病薬を目指した新規オキシカムA環芳香族複素環アナログの創製

    鶴岡 航太朗, 小町 元輝, 鈴木 啓太, 高橋 恭子, 中村 成夫, 大江 知之, 大久保 知子, 眞鍋 貴之, 田﨑 嘉一, 増野 匡彦

    日本薬学会第141年会  2021.3 

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Industrial property rights

  • パーキンソン病治療薬

    増野 匡彦, 大江 知之, 高橋 恭子, 安田 大輔, 田▲崎▼ 嘉一

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    Applicant：学校法人慶應義塾

    Application no：JP2020003462  Date applied：2020.1

    Publication no：WO2020-158870  Date published：2020.8

    J-GLOBAL

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  • パーキンソン病治療薬

    増野 匡彦, 大江 知之, 高橋 恭子, 安田 大輔, 田▲崎▼ 嘉一

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    Applicant：慶應義塾

    Application no：JP2020003462  Date applied：2020.1

    Patent/Registration no：特許第7402467号  Date registered：2023.12 

    J-GLOBAL

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  • 光学活性6-オキソ-3,5-ジヒドロキシヘキサン酸誘導体の製造方法

    南 達哉, 高橋 恭子, 檜山 爲次郎, 小原 義夫

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    Applicant：財団法人相模中央化学研究所

    Application no：特願平4-259939  Date applied：1992.9

    Announcement no：特開平6-107592  Date announced：1994.4

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Research Projects

  • Development of novel heart disease drugs based on nitric oxide production

    Grant number：23K06035  2023.4 - 2026.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

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    Grant amount：\3380000 （ Direct Cost: \2600000 、 Indirect Cost：\780000 ）

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  • Development of new-type antioxidant based on the structure of ascorbic acid

    Grant number：18590105  2006 - 2008

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    TAKAHASHI Kyoko

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    Grant amount：\2600000 （ Direct Cost: \2300000 、 Indirect Cost：\300000 ）

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  • Development of fullerene derivatives for new anti-cancer and and-virus drugs lead compounds

    Grant number：17590092  2005 - 2007

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    MASHINO Tadahiko, NAKAMURA Shigeo, TAKAHASHI Kyoko, NISHIZAWA Thiho

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    Grant amount：\3710000 （ Direct Cost: \3500000 、 Indirect Cost：\210000 ）

    1. Cancer cell proliferation inhibition mechanism of fullerene derivatives.
    It had already been reported that the pyrrolidinium type fullerene derivative (1) showed the cancer cell proliferation inhibition effect. We investigated the mechanism of inhibition using HL-60 cell line. Treatment of 1 induced the features of apoptosis and also induced the Caspase 3 and 9 activation and cytochromec release from mitochondria. But p53 induction was not observed. It is thought that the compound causes apoptosis without p53 induction is advantageous as the anti-cancer drug, because p53 is loss in cancer cells in many cases.
    2. Design and synthesis of praline type fullerene derivatives with high HIV reverse transcriptase inhibition activity.
    Using the computer docking simulation, various fullerene derivatives were designed and synthesized based on the structure of derivative (2) that had three carboxylic acids in the pyrrole ring. Relationship between the inhibition activity and number and position of carboxylic acid acids in the pyrrole ring was investigated and more active derivative 3 was developed. The inhibition activity of 3 was 100 times or more high than Nevirapin, which is used as and HIV drug.
    3. Anti-hepatitis C virus activity of fullerene derivatives
    Sulfonium type fullerene derivative (4) showed excellent hepatitis C virus RNA polymerase inhibition activity and hepatitis C virus growth inhibition activities. Cytotoxicity of 4 was low. 4 is a promising lead compound of the anti-hepatitis C virus medicine.
    In this three years project, we developed the novel promising lead compounds for anti-cancer, anti-HIV, and anti-HCV medicine.

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  • コレステロール生合成阻害剤トリパラノールの光学活性体の合成とその生物活性

    Grant number：07772107  1995

    日本学術振興会  科学研究費助成事業  奨励研究(A)

    高橋 恭子

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    Grant amount：\800000 （ Direct Cost: \800000 ）

    ラセミ体のトリパラノールは4-ヒドロキシベンズアルデヒドから4工程、約60%で合成した。光学分割剤として種々の光学活性カルボン酸類を検討した結果、光学活性タートラニル酸を用いる方法のみが光学活性体を与えた。ラセミ体からの収率は10-20%とやや低いものの、得られるトリパラノールの光学純度は両対掌体とも98%以上であることを光学活性カラムを用いるHPLCにより確認した。得られた光学活性トリパラノールの阻害活性を調べるため、阻害活性試験条件を探索した。ラット肝のホモジネートを酵素源とし、^<13>C-ラベルしたデスモステロールを基質としてインキュベートすると相当する^<13>C-ラベルしたコレステロールが得られ、その変換率は^<13>C-NMRの各ピーク積分値から算出できる。この酵素反応を詳細な検討により最適化し、変換率80-90%の条件を確立した。阻害剤としてトリパラノールのラセミ体、(+)-体、(-)-体をそれぞれ基質と同量(280μM)添加すると、コレステロールへの変換はいずれもほぼ完全に阻害された。また阻害剤の量を基質に対し5-50%としてそれぞれ試験した結果、阻害活性は用量依存性であること、10%(28μM)使用にて阻害率は約50%であることがわかった。ラセミ体、(+)-体、(-)-体の阻害活性の強さに有意差は見られなかった。本研究によりトリパラノールは両対掌ともにラット肝におけるコレステロール生合成(デスモステロールの還元反応)を阻害することが明らかとなった。唯一の不斉部位である3級アルコールは活性発現に必須であると考えられるが、その立体配置は活性に影響しないという結果は興味深い。さらに副作用である白内障誘発について活性と立体配置の関係を調査し、作用福作用の分離を試みたい。

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Teaching Experience

  • CHEMISTRY OF BIOACTIVE SUBSTANCES

    Institution：Keio University

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  • DOCTORAL LECTURE ON CHEMICAL PHARMACY 1

    Institution：Keio University

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  • 卒業研究１（薬学科）

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  • PHARMACEUTICAL-ENGLISH SEMINAR

    Institution：Keio University

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  • RESEARCH FOR BACHELOR'S THESIS 1

    Institution：Keio University

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  • DRUG DISCOVERY SCIENCES

    Institution：Keio University

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  • MEDICINAL CHEMISTRY 1

    Institution：Keio University

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  • 医薬品製造化学

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  • 創薬・有機化学特論

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  • 卒業研究（薬科学科）

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  • ADVANCED MEDICINAL AND ORGANIC CHEMISTRY

    Institution：Keio University

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  • BACHELOR'S THESIS

    Institution：Keio University

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  • EARLY EXPOSURE TO INDUSTRY

    Institution：Keio University

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  • ENGLISH EXERCISES FOR PHARMACEUTICAL SCIENCES

    Institution：Keio University

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  • DRUG SYNTHESIS AND PROCESS CHEMISTRY

    Institution：Keio University

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  • DRUG SYNTHESIS LABORATORY COURSE

    Institution：Keio University

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  • PHARMACEUTICAL-ENGLISH SEMINAR A

    Institution：Keio University

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  • RESEARCH APPARATUS LABORATORY COURSE

    Institution：Keio University

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  • MOLECULAR DESIGN OF MEDICINE

    Institution：Keio University

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  • ORGANIC SYNTHESIS

    Institution：Keio University

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  • SEMINAR: (BIOORGANIC AND MEDICINAL CHEMISTRY)

    Institution：Keio University

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  • STUDY OF MAJOR FIELD: (BIOORGANIC AND MEDICINAL CHEMISTRY)

    Institution：Keio University

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  • RESEARCH FOR BACHELOR'S THESIS A

    Institution：Keio University

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  • 化学系薬学特論Ⅰ

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  • 英語演習（薬科学科）

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  • 医薬分子設計化学

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  • 医薬品化学実習

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  • 早期体験学習（薬科学科）

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  • 高度研究機器特別演習

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  • 卒業研究Ａ

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  • 精密有機合成

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  • 薬学英語演習Ａ

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  • 演習（医薬品化学）

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  • 課題研究（医薬品化学）

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  • 創薬科学特論

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  • 医薬品化学１

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  • 生理活性物質化学特論

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