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Preparaion of Novel Anticancer Agents based on Isoquinoline Marine Natural Products

Research Project

Project/Area Number 15K07873
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMeiji Pharmaceutical University

Principal Investigator

Saito Naoki  明治薬科大学, 薬学部, 教授 (80142545)

Co-Investigator(Kenkyū-buntansha) 木村 真也  明治薬科大学, 薬学部, 助手 (10632739)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords海洋天然物 / 抗腫瘍活性 / テトラヒドロイソキノリン / 全合成 / 殺細胞活性 / エクチナサイジン / レニエラマイシン / ラジカル反応 / 化学変換 / 構造活性相関 / 反応機構 / 構造解析
Outline of Final Research Achievements

① Preparation of eleven new ecteinascidin derivatives to receive some additional proof of cytotoxicity profiles; ② Preparation of a variety of renieramycin derivatives for discovering highly potent anticancer activity; ③ The first total synthesis of renieramycin T; ④ Preparation of both right-half and left-had models of saframycin-renieramycins along with evaluation for cytotoxicity profiles; ⑤Total synthesis of renieramycin I and also Structure determination of 7-desmethylrenieramycin O; ⑥ Discovered a novel photo-transformation from methoxy-p-quinone into a characteristic highly substituted A-ring of ecteinascidins and renieramycin T.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (39 results)

All 2018 2017 2016 2015

All Journal Article (14 results) (of which Int'l Joint Research: 10 results,  Peer Reviewed: 13 results,  Open Access: 12 results,  Acknowledgement Compliant: 7 results) Presentation (24 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results) Book (1 results)

  • [Journal Article] Preparation of Chiral Right-half Models of Antitumor Bistetrahydroisoquinolinequinone Natural Products2018

    • Author(s)
      Senbonmatsu Y.、Kimura S.、Akiba M.、Ando S. Saito N.
    • Journal Title

      HETEROCYCLES

      Volume: 97 Issue: 2 Pages: 1050-1067

    • DOI

      10.3987/com-18-s(t)88

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Semisynthesis and biological evaluation of prenylated resveratrol derivatives as multi-targeted agents for Alzheimer's disease2017

    • Author(s)
      Puksasook T., Kimura S., Tadtong S., Jiaranakulwanitch J., Pratungdejkul J., Kitphari W., Suwanborirux K., Saito N. Nukoolkarn V.
    • Journal Title

      J. Nat. Med.

      Volume: 71 Issue: 4 Pages: 665-682

    • DOI

      10.1007/s11418-017-1097-2

    • NAID

      40021337926

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Chemistry of renieramycins. 17. A new generation of renieramycins: 5-O-monohydroquinone analogues of renieramycin M as potential cytotoxic agents against non-small-cell lung cancer cells2017

    • Author(s)
      Chamni S., Sirimangkalakitti N., Chanvorachote P., Saito N., Suwanborirux K.
    • Journal Title

      J. Nat. Prod.

      Volume: 80 Pages: 1541-1547

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Apoptosis-inducing Effect of Hydroquinone 5-O-Cinnamoyl Ester Analog of Renieramycin M on Non-small Cell Lung Cancer Cells2017

    • Author(s)
      Matuthed A., Pinkhien T., Chamni S., Suwanborirux K., Saito N., Petpiroon N., Chanvorachote C.
    • Journal Title

      Anticancer Research

      Volume: 37 Issue: 11 Pages: 6259-6267

    • DOI

      10.21873/anticanres.12077

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] 天然物をツール・情報源とする低分子医薬品の創薬研究2017

    • Author(s)
      齋藤直樹
    • Journal Title

      ファルマシア

      Volume: 53 Pages: 555-559

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Chemistry of renieramycins. 16. Structure of 7-desmethylrenieramycin O (= 14a-hydroxyrenieramycin S) from blue sponge, Xestospongia sp.2017

    • Author(s)
      Saito N., Hiramatsu A., Hirade H., Kubota M., Toyoshima R., Fujino A., Sirimangkalakitti N., Suwanborirux K., Concepcion G. P..
    • Journal Title

      Heterocycels

      Volume: 95 Issue: 2 Pages: 748-752

    • DOI

      10.3987/com-16-s(s)77

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Chemistry of renieramycins. 17. A new generation of renieramycins: Hydroquinone 5-O-monoester analogues of renieramycin M as potential cytotoxicity agents against non-small -cell lung cancer cell2017

    • Author(s)
      Chamni S., Sirimangkalakitti N., Chanvorachote P., Saito N., Suwanborirux k.
    • Journal Title

      J. Nat. Prod.

      Volume: 80 Issue: 5 Pages: 1541-1547

    • DOI

      10.1021/acs.jnatprod.7b00068

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Chemistry of renieramycins. Part 15. Synthesis of 22-O-ester derivatives of jorunnamycin A and their cytotoxicity against nonsmall lung cancer cells2016

    • Author(s)
      Sirimangkalakitti N., Chamni S., Charupant K., Chanvorachote P., Mori N., Saito N., Suwanborirux K.
    • Journal Title

      J. Nat. Prod.,

      Volume: 79 Issue: 8 Pages: 2089-2093

    • DOI

      10.1021/acs.jnatprod.6b00433

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Bishydroquinone renieramycin M induced human lung cancer cell apoptosis through mitochondria-dependent pathway2016

    • Author(s)
      Pinkhien T., Maiuthes A., Chamni S., Suwanborirux K., Saito N., Chanvorachote P.
    • Journal Title

      Anticancer Res.

      Volume: 36 Issue: 12 Pages: 6327-6333

    • DOI

      10.21873/anticanres.11229

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Practical synthesis of tricyclic lactam model of antitumor renieramycin-saframycin natural products2016

    • Author(s)
      Yokoya M., Fujino A., Yaguchi A., Yamazaki M., Saito N.
    • Journal Title

      Heterocycles

      Volume: 93 Issue: 2 Pages: 802-802

    • DOI

      10.3987/com-15-s(t)53

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Stereoselective total synthesis of (-)-renieramycin T2016

    • Author(s)
      Yokoya M., Toyoshima R., Suzuki T., Le V. H., Williams R. M., Saito N.
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 10 Pages: 0001-0009

    • DOI

      10.1021/acs.joc.6b00327

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Chemistry of ecteinascidins. Part 5. An additional proof of cytotoxicity evaluation of ecteinascidin 770 derivatives2016

    • Author(s)
      Toyoshima R., Mori N., Suzuki T., Lowtangkicharoen W., Suwanborirux K., Saito N.
    • Journal Title

      Chem. Pharm. Bull.

      Volume: 65 Pages: 0000-0007

    • NAID

      130005160038

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Chemistry of renieramycins. Part 14. Total synthesis of renieramycin I and practical synthesis of cribrostatin 4 (renieramycin H)2015

    • Author(s)
      Yokoya M., Kobayashi K. Sato M., Saito N.
    • Journal Title

      Marine Drugs

      Volume: 13 Issue: 8 Pages: 4915-4933

    • DOI

      10.3390/md13084915

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] 抗腫瘍活性レニエラマイシン海洋天然物の化学的研究2015

    • Author(s)
      横屋正志、齋藤直樹
    • Journal Title

      有機合成化学協会誌

      Volume: 73 Pages: 723-736

    • NAID

      130005093745

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] 1.3-ジオキサシクロペンタン環を生じる新規光反応前駆体の柔軟な合成法の開発2018

    • Author(s)
      高橋昇平、横屋正志、齋藤直樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 含窒素複素環キノンに対する新規光反応の開発2018

    • Author(s)
      望月 萌、横屋正志、齋藤直樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Renieramycin類の光学活性CDE環モデルの合成2018

    • Author(s)
      松原健治、横屋正志、Nachanun Sirimangkalakitti、齋藤直樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 生物活性イソキノリン抗生物質を基軸とする新規認知症改善薬の創製2018

    • Author(s)
      Nachanun Sirimangkalakitti、中井啓陽、山﨑未来、紀嘉浩、佐藤準一,、齋藤直樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 新規極微量海洋天然物7-demethylrenieramycin Oと誘導体の合成研究2018

    • Author(s)
      門傅研人、横屋正志、佐藤充浩、小林恵一郎、齋藤直樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 抗腫瘍活性を有するテトラヒドロイソキノリン系天然物の合成研究2018

    • Author(s)
      木村真也、齋藤直樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 新規極微量海洋天然物レニエラマイシンYの合成アプローチ2018

    • Author(s)
      小林 翔、横屋正志、丸山 崚、齋藤直樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 生物活性新規イソキノリンアルカロイドFennebricin A及びBの全合成研究2017

    • Author(s)
      門傅 研人、横屋 正志、佐藤 充浩、小林 恵一郎、齋藤 直樹
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学(仙台)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 光変換反応を利用した1,3-ジオキサシクロペンタン環の形成2017

    • Author(s)
      高橋 昌平、横屋 正志、山﨑 未来、齋藤 直樹
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学(仙台)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 強力な抗腫瘍活性を有するビステトラヒドロイソキノリン系天然物の合成研究2017

    • Author(s)
      木村 真也、齋藤 直樹
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学(仙台)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Succcessful international collaborative medicinal chemistry of biologically active marine natural products based on Thai marine oranagisms2017

    • Author(s)
      Saito N
    • Organizer
      The JSPS-NRCT follow-up seminar 2017 and 33rd international annual meeting in Pharmaceutical Sciences
    • Place of Presentation
      バークレーホテル(バンコク)
    • Year and Date
      2017-03-02
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry of biologically active natural 1,2,3,4-tertahydroisoquinoline: Unpredictable photochemical transformation of renieramycin type p-quinone into ecteinscidin type phenol2017

    • Author(s)
      Saito N., Nakai K., Yamazaki M., Yokoya M.
    • Organizer
      26th International synposium of heterocyclic chemistry (ISHC) congress
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 相関移動触媒を用いた光学活性チロシン誘導体の合成2017

    • Author(s)
      安齋 凌、横屋正志、齋藤直樹
    • Organizer
      第61回日本薬学会関東支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Renieramycin類の光学活性CDE環モデルの合成2017

    • Author(s)
      松原健治、横屋正志、齋藤直樹
    • Organizer
      第61回日本薬学会関東支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 抗腫瘍活性イソキノリン系天然物の化学的展開と創薬リードの創製2017

    • Author(s)
      横屋正志、Nachanun Sirimangkalakitti、Supakarn Chamni、望月 萌、鈴木俊宏、齋藤直樹
    • Organizer
      第35回メディシナルケミストリーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 強力な抗腫瘍活性を有するビステロラヒドロイソキノリン天然物の合成研究2017

    • Author(s)
      木村真也、齋藤直樹
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 海洋天然物7-デメチルレニエラマイシンOの全合成及びフェネブリシン類の合成2017

    • Author(s)
      門傅研人、佐藤充浩、小林恵一郎、横屋正志、齋藤直樹
    • Organizer
      第74回有機合成化学協会関東支部シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 新規海洋天然物レニエラマイシンYの合成研究2016

    • Author(s)
      丸山 崚、横屋 正志、齋藤 直樹
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      清水市清水文化会館(静岡)
    • Year and Date
      2016-11-06
    • Related Report
      2016 Research-status Report
  • [Presentation] Chemistry of antitumor isoquinoline marine natural products: Total synthesisi of (-)-renieramycin T2016

    • Author(s)
      Saito N.
    • Organizer
      3rd Symposium of Showa Pharmaceutical University (SPU) innovative pharmaceutical analysis of covalent modification in biomolecules
    • Place of Presentation
      昭和薬科大学(東京)
    • Year and Date
      2016-08-31
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 抗腫瘍活性エクチナサイジン海洋天然物の合成と生物活性2015

    • Author(s)
      森ななえ、豊嶋涼子、藤野晃也、鈴木俊宏、横屋正志、齋藤直樹、Khanit Suwanborirux
    • Organizer
      第33回メディシナルケミストリーシンポジウム
    • Place of Presentation
      千葉
    • Year and Date
      2015-11-25
    • Related Report
      2015 Research-status Report
  • [Presentation] 海洋天然物クリブロスタチン4の改良合成およびレニエラマイシンIの全合成2015

    • Author(s)
      佐藤充浩、小林恵一郎、横屋正志、齋藤直樹
    • Organizer
      第70回記念有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      長岡
    • Year and Date
      2015-11-21
    • Related Report
      2015 Research-status Report
  • [Presentation] 抗腫瘍活性微量天然物レニエラマイシンTの不斉全合成2015

    • Author(s)
      t豊嶋涼子、横屋正志、齋藤直樹、Le. H. V., Williams R. M.
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] レニエラマイシン系海洋天然物のキラル合成アプローチ2015

    • Author(s)
      豊嶋涼子、横屋正志、齋藤直樹
    • Organizer
      第59回日本薬学会関東支部大会
    • Place of Presentation
      千葉
    • Year and Date
      2015-09-12
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthetic studies on a total synthesis of antitumor renieramycin T2015

    • Author(s)
      Yokoya M., Toyoshima R., Saito N., Le V. H., Williams R. M.
    • Organizer
      25th International Symposium of Heterocyclic Chemistry
    • Place of Presentation
      California (USA)
    • Year and Date
      2015-08-25
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Book] アルカロイドの科学2017

    • Author(s)
      高山 廣光
    • Total Pages
      560
    • Publisher
      化学同人
    • ISBN
      9784759814187
    • Related Report
      2017 Annual Research Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

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