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Synthetic Studies of Maitotoxin to Elucidate Mode-of-Action

Research Project

Project/Area Number 24245009
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKyushu University

Principal Investigator

Oishi Tohru  九州大学, 理学(系)研究科(研究院), 教授 (90241520)

Co-Investigator(Kenkyū-buntansha) KONOKI Keiichi  東北大学, 大学院農学研究科, 准教授 (40292825)
TORIKAI Kohei  九州大学, 大学院理学研究院, 助教 (20456990)
EBINE Makoto  九州大学, 大学院理学研究院, 助教 (70545574)
Project Period (FY) 2012-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥46,930,000 (Direct Cost: ¥36,100,000、Indirect Cost: ¥10,830,000)
Fiscal Year 2015: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2014: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥9,100,000 (Direct Cost: ¥7,000,000、Indirect Cost: ¥2,100,000)
Fiscal Year 2012: ¥27,430,000 (Direct Cost: ¥21,100,000、Indirect Cost: ¥6,330,000)
Keywordsマイトトキシン / 梯子状ポリエーテル / 化学合成 / カルシウムイオン流入活性 / 部分構造 / 生物活性 / カルシウムイオン / 有機合成化学 / 構造活性相関 / 分子プローブ / 作用標的タンパク質
Outline of Final Research Achievements

Maitotoxin (MTX) is a marine toxin produced by the dinoflagellate. The structure-activity relationship of MTX was studied by using synthetic partial structures of MTX. MTX induced Ca2+ influx activity was inhibited by the hydrophobic part corresponding to the C’-F’ and QRS ring, and the IC50 values were estimated to be ca.50 microM, respectively. The inhibitory activity of the QR(S) ring in which the seven-membered S-ring was substituted with six-membered ring, was reduced in ca. six times. However, the NOPQR(S) ring possessing both hydrophobic and hydrophilic moiety was not active. The inhibitory activity of the LMNO ring corresponding to the hydrophilic moiety was less active than that of the hydrophobic part, and there was no significant difference between the enantiomers.

Report

(5 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (47 results)

All 2016 2015 2014 2013 2012 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Acknowledgement Compliant: 1 results) Presentation (36 results) (of which Int'l Joint Research: 5 results,  Invited: 10 results) Book (1 results) Remarks (2 results)

  • [Journal Article] Synthesis and Biological Activity of the QRS Ring System of Maitotoxin2014

    • Author(s)
      Hisaaki Onoue, Tomomi Baba, Keiichi Konoki, Kohei Torikai, Makoto Ebine, and Tohru Oishi
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 12 Pages: 1904-1906

    • DOI

      10.1246/cl.140789

    • NAID

      130004690780

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Biological Activity of the C'D'E'F' Ring System of Maitotoxin2014

    • Author(s)
      Kunitake, M.; Oshima, T.; Konoki, K.; Ebine, M.; Torikai, K.; Murata, M.; Oishi, T.
    • Journal Title

      J. Org. Chem.

      Volume: (in press) Issue: 11 Pages: 4948-4962

    • DOI

      10.1021/jo5005235

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and structure revision of the C43-C67 part of amphidinol 32013

    • Author(s)
      M. Ebine, M. Kanemoto, Y. Manabe, Y. Konno, K. Sakai, N. Matsumori, M. Murata, T. Oish
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 11 Pages: 2846-2849

    • DOI

      10.1021/ol401176a

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Novel Sperm-Activating and Attracting Factor (SAAF) from the Ascidian Ascidia sydneiensis.2013

    • Author(s)
      Matsumori, N., Hiradate, Y., Shibata, H., Oishi, T., Simma, S., Toyoda, M., Hayashi, F., Yoshida, M, Murata, M, and Morisawa, M.
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 2 Pages: 294-297

    • DOI

      10.1021/ol303172n

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Convergent Method via α-Cyano Ethers: A Powerful Strategy for Synthesizing Ladder-Shaped Polyethers2012

    • Author(s)
      Tohru Oishi
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 70 Issue: 11 Pages: 1170-1177

    • DOI

      10.5059/yukigoseikyokaishi.70.1170

    • NAID

      10031131196

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Confirmation of the Absolute Configuration at C45 of Amphidinol 32012

    • Author(s)
      Yoshiyuki Manabe
    • Journal Title

      Journal of Natural Products

      Volume: 75 Issue: 11 Pages: 2003-2006

    • DOI

      10.1021/np300604w

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Artificial ladder-shaped polyethers that inhibit maitotoxin-induced Ca2+ influx in rat glioma C6 cells2012

    • Author(s)
      Oishi, T.; Konoki, K.; Tamate, R.; Torikai, K.; Hasegawa, F.; Matsumori, N.; Murata, M.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 22 Issue: 11 Pages: 3619-3622

    • DOI

      10.1016/j.bmcl.2012.04.053

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Comprehensive Molecular Motion Capture for Sphingomyelin by Site-Specific Deuterium Labeling2012

    • Author(s)
      Nobuaki Matsumori
    • Journal Title

      Biochemistry

      Volume: 51 Issue: 42 Pages: 8363-8370

    • DOI

      10.1021/bi3009399

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] マイトトキシンのLM環部の合成研究2016

    • Author(s)
      岸上隼大・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-25
    • Related Report
      2015 Annual Research Report
  • [Presentation] マイトトキシンの C5-C15 部分の合成研究2016

    • Author(s)
      柿山 和輝・海老根 真琴・鳥飼 浩平・大石 徹
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-25
    • Related Report
      2015 Annual Research Report
  • [Presentation] C-グリコピラノシドのフローマイクロ合成2016

    • Author(s)
      神徳 瑞生・岸上 隼人・鳥飼 浩平・海老根 真琴・大石 徹
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-25
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthetic Study of the C1-C15 Part of Maitotoxin2016

    • Author(s)
      Kazuteru Kakiyama, Kohei Torikai, Makoto Ebine, Tohru Oishi
    • Organizer
      The 5th International Conference on MEXT Project of Integrated Research on Chemical Synthesis
    • Place of Presentation
      名古屋大学
    • Year and Date
      2016-01-29
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthetic Study of the LM Ring of Maitotoxin2015

    • Author(s)
      Hayato Kishigami, Kohei Torikai, Makto Ebine, Tohru Oishi
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      ハワイ,米国
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and biological activity of the NOPQRS ring system of maitotoxin2015

    • Author(s)
      Hisaaki Onoue, Kohei Torikai, Makoto Ebine, Tohru Oishi
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      ハワイ,米国
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis of Partial Structures2015

    • Author(s)
      Tohru Oishi
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      ハワイ,米国
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] マイトトキシンのBCD環部の合成研究2015

    • Author(s)
      藥師寺 宏幸・久保 拓也・鳥飼 浩平・海老根 真琴・大石 徹
    • Organizer
      第5回CSJフェスタ2015
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] マイトトキシンのent-LMNO環部の合成研究2015

    • Author(s)
      丸林里帆、鳥飼浩平、海老根真琴、大石 徹
    • Organizer
      第27回若手研究者のためのセミナー
    • Place of Presentation
      九州大学 馬出キャンパス コラボステーション
    • Year and Date
      2015-08-29
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] マイトトキシンのLM環部の合成研究2015

    • Author(s)
      岸上隼大、鳥飼浩平、海老根真琴、大石 徹
    • Organizer
      第27回若手研究者のためのセミナー
    • Place of Presentation
      九州大学 馬出キャンパス コラボステーション
    • Year and Date
      2015-08-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] マイトトキシンのent-LMNO環部の合成研究2015

    • Author(s)
      丸林里帆、鳥飼浩平、海老根真琴、大石 徹
    • Organizer
      第52回化学関連合同支部大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] マイトトキシンのL環部の合成研究2015

    • Author(s)
      岸上 隼大、鳥飼 浩平、海老根 真琴、大石 徹
    • Organizer
      第52回化学関連合同支部大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] マイトトキシンのWXYZ環部の合成研究2015

    • Author(s)
      當間佳樹、鳥飼浩平、海老根真琴、大石 徹
    • Organizer
      第52回化学関連合同支部大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthetic Study of the NOPQRS Ring System of Maitotoxin2015

    • Author(s)
      Hisaaki Onoue, Kohei Torikai, Makoto Ebine, Tohru Oishi
    • Organizer
      日本化学会九州支部設立100周年記念国際シンポジウム
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] マイトトキシンのQRS環部およびNOPQR(S)環部の合成研究2015

    • Author(s)
      尾上久晃、鳥飼浩平、海老根真琴、大石 徹
    • Organizer
      第26回万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター
    • Year and Date
      2015-06-06
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] マイトトキシンのQRS環部およびNOPQR(S)環部の合成研究2015

    • Author(s)
      尾上久晃、鳥飼浩平、海老根真琴、大石 徹
    • Organizer
      第25回記念万有福岡シンポジウム
    • Place of Presentation
      九州大学医学部百年講堂
    • Year and Date
      2015-05-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] マイトトキシンのWXYZ環部の合成研究2015

    • Author(s)
      當間 佳樹・鳥飼 浩平・海老根 真琴・大石 徹
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 船橋キャンパス
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] マイトトキシンのent-LMNO環部の合成研究2015

    • Author(s)
      丸林 里帆・鳥飼 浩平・海老根 真琴・大石 徹
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 船橋キャンパス
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] マイトトキシンのNOPQRS環部の合成研究2015

    • Author(s)
      尾上 久晃・石川 絵理奈・鳥飼 浩平・海老根 真琴・此木 敬一・大石 徹
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 船橋キャンパス
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] マイトトキシンのNOPQRS環部の合成研究2014

    • Author(s)
      尾上久晃・石川絵理奈・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      第26回若手研究者のためのセミナー
    • Place of Presentation
      九州大学 馬出キャンパス コラボステーション
    • Year and Date
      2014-11-22
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] マイトトキシンのNOPQRS環部の合成研究2014

    • Author(s)
      尾上久晃・石川絵理奈・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      第31回有機合成化学セミナー
    • Place of Presentation
      休暇村 志賀島
    • Year and Date
      2014-09-17 – 2014-09-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] 人工梯子状ポリエーテルの超効率的合成法の開発とイオンチャネルに対する作用解明2014

    • Author(s)
      大石 徹
    • Organizer
      2014旭硝子財団助成研究発表会
    • Place of Presentation
      ホテルグランドヒル市ヶ谷
    • Year and Date
      2014-07-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] マイトトキシンのNOPQRS環部の合成研究2014

    • Author(s)
      尾上久晃・石川絵理奈・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      第51回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2014-06-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] マイトトキシンのLMNO環部の合成研究2014

    • Author(s)
      丸林 里帆・石川絵理奈・鳥飼 浩平・海老根 真琴・大石 徹
    • Organizer
      第51回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2014-06-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] マイトトキシンのQRS環部およびC’D’E’F’環部の合成と生物活性2014

    • Author(s)
      尾上久晃・國武政宏・鳥飼浩平・海老根真琴・此木敬一・村田道雄・大石 徹
    • Organizer
      日本ケミカルバイオロジー学会 第9回年会
    • Place of Presentation
      大阪大学豊中キャンパス
    • Year and Date
      2014-06-11 – 2014-06-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of Ladder-shaped Polyethers by Using Microflow Reactors2013

    • Author(s)
      Tohru Oishi
    • Organizer
      The Eighth International Symposium on Integrated Synthesis (ISIS-8)
    • Place of Presentation
      Todaiji Temple Cultural Center, Nara, Japan
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Fluorine Labeled Natural Products for Solid-State NMR Measurements2013

    • Author(s)
      Tohru Oishi
    • Organizer
      4 th International Fluorine Workshop, Tokyo
    • Place of Presentation
      Tokyo Institute of Technology, Tokyo, Japan
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 機能解明を志向した生物活性分子の設計・合成・評価2013

    • Author(s)
      大石 徹
    • Organizer
      第24回 万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 機能解明を志向した生物活性分子の設計・合成・評価2013

    • Author(s)
      大石 徹
    • Organizer
      第25回 若手研究者のためのセミナー
    • Place of Presentation
      九州大学馬出キャンパス・コラボステーション
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 膜タンパク質との相互作用解明を志向した梯子状ポリエーテルの設計と合成

    • Author(s)
      大石 徹
    • Organizer
      第49回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] マイトトキシンのQRS環部の合成研究

    • Author(s)
      馬場萌未・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      第22回万有福岡シンポジウム
    • Place of Presentation
      九州大学医学部百年講堂
    • Related Report
      2012 Annual Research Report
  • [Presentation] マイトトキシンのQRS環部の合成研究

    • Author(s)
      馬場萌未・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      第49回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Related Report
      2012 Annual Research Report
  • [Presentation] マイトトキシンのC’D’E’F’環部の合成研究

    • Author(s)
      國武政宏・大島崇宏・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      第49回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Related Report
      2012 Annual Research Report
  • [Presentation] マイトトキシンのNOPQRS環部の合成研究

    • Author(s)
      馬場萌未・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      第24回若手研究者のためのセミナー
    • Place of Presentation
      九州大学馬出キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] マイトトキシンのQRS環部の合成研究

    • Author(s)
      馬場萌未・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      日本化学会第93春季年会(2013)
    • Place of Presentation
      立命館大学くさつ・びわこキャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] マイトトキシンのQRS環部の合成研究

    • Author(s)
      國武政宏・鳥飼浩平・海老根真琴・大石 徹
    • Organizer
      日本化学会第93春季年会(2013)
    • Place of Presentation
      立命館大学くさつ・びわこキャンパス
    • Related Report
      2012 Annual Research Report
  • [Book] Chembiomolecular Science: At the Frontier of Chemistry and Biology2012

    • Author(s)
      Tohru Oishi
    • Total Pages
      341
    • Publisher
      Springer
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.scc.kyushu-u.ac.jp/Seibutsuyuki/index.htm

    • Related Report
      2015 Annual Research Report
  • [Remarks] 九州大学理学部化学科生物有機化学研究室

    • URL

      http://www.scc.kyushu-u.ac.jp/Seibutsuyuki/index.htm

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2013-05-15   Modified: 2019-07-29  

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