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Design and synthesis of artificial receptors for disease-related oligosaccharides, and their applications for controlling cell functions

Research Project

Project/Area Number 22710220
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Living organism molecular science
Research InstitutionKeio University

Principal Investigator

TAKAHASHI Daisuke  慶應義塾大学, 理工学部, 助教 (00509929)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2011: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords糖鎖 / 分子デザイン / 合成 / ボロン酸 / 分子認識 / 低分子レセプター / 結核 / シアル酸 / 糖鎖認識 / ガン転移 / ガラクトフラノシド / 人工低分子レセプター / 光分解 / 人工レセプター
Research Abstract

Small molecules, which selectively bind to and effectively photodegrade target disease-related oligosaccharides under mild conditions, were designed and synthesized. It was found that synthesized anthraquinone(AQ)-or fullerene-boronic acid hybrids selectively bound to and photodegraded.-D-galactofuranoside, which is a sugar component of mycobacterial cell wall. In addition, it was found that photodegradation of the target oligosaccharides on the bacterial cell wall by AQ-boronic acid hybrid took place and induced significant whole-cell destruction. Furthermore, several molecules that bind to sialic acid were designed and synthesized. The results obtained from this study will contribute to the molecular design of photodegrading agents for cancer-related oligosaccharides.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (20 results)

All 2012 2011 2010 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (13 results) Remarks (2 results)

  • [Journal Article] Chemical methods for degradation of target oligosaccharides using designed light-activatable organic molecules2012

    • Author(s)
      高橋大介
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 37 Pages: 4397-4407

    • DOI

      10.1039/c2cc17384k

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Target-selective photodegradation of oligosaccharides by a fullerene-boronic acid hybrid upon visible light irradiation2011

    • Author(s)
      D. Takahashi, K. Toshima
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 11712-11714

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Target-selective photodegradation of oligosaccharides by a fullerene-boronic acid hybrid upon visible light irradiation2011

    • Author(s)
      高橋大介
    • Journal Title

      Chemical Communications

      Volume: 47 Issue: 42 Pages: 11712-11714

    • DOI

      10.1039/c1cc15646b

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Target-selective photodegradation of oligosaccharides by light-activated small molecules2010

    • Author(s)
      D. Takahashi, S. Hirono, C. Hayashi, M. Igarashi, Y. Nishimura, K. Toshima
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 49 Pages: 10096-10100

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Photodegradation of Target Oligosaccharides by Light-Activated Small Molecules.2010

    • Author(s)
      高橋大介
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 49 Pages: 10096-10100

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Target-selective photodegradation of oligosaccharides by light-activated small molecules2011

    • Author(s)
      D. Takahashi, S. Hirono, K. Toshima
    • Organizer
      MDF International Workshop : Open-shell Organic Molecules-Synthesis and Electronic Structure Freedom-;"New Frontier of Materials Science Opened by Molecular Degree of Freedom"
    • Place of Presentation
      Osaka
    • Year and Date
      2011-10-07
    • Related Report
      2011 Final Research Report
  • [Presentation] Target-selective photodegradation of oligosaccharides by light-activated small molecules2011

    • Author(s)
      高橋大介
    • Organizer
      MDF International Workshop : Open-shell Organic Molecules-Synthesis and Electronic Structure Freedom-
    • Place of Presentation
      梅田スカイビル(大阪)
    • Year and Date
      2011-10-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] Development of an inovative method for target-selective photodegradation of oligosaccharides by light-activated small molecules2011

    • Author(s)
      D. Takahashi, S. Hirono, C. Hayashi, M. Igarashi, Y. Nishimura, K. Toshima
    • Organizer
      The 31th Naito Conference on Glycan Expression and Regulation [II]
    • Place of Presentation
      Sapporo
    • Year and Date
      2011-09-14
    • Related Report
      2011 Final Research Report
  • [Presentation] Development of an innovative method for target-selective photodegradation of oligosaccharides by light-activated small molecules2011

    • Author(s)
      高橋大介
    • Organizer
      The 31th Naito Conference on Glycan Expression and Regulation [II]
    • Place of Presentation
      シャトレーゼガトーキングダム札幌(北海道)
    • Year and Date
      2011-09-14
    • Related Report
      2011 Annual Research Report
  • [Presentation] フラーレン-ボロン酸ハイブリッドによる標的糖鎖の選択的光分解2011

    • Author(s)
      廣野信悟、高橋大介、戸嶋一敦
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学
    • Year and Date
      2011-03-27
    • Related Report
      2011 Final Research Report
  • [Presentation] 結核菌の構成糖鎖を選択的に光分解する光感受性人工生体機能分子の創製2010

    • Author(s)
      高橋大介、廣野信悟、林千草、五十嵐雅之、西村吉雄、戸嶋一敦
    • Organizer
      GlycoTOKYO2010シンポジウム
    • Place of Presentation
      東京大学本郷キャンパス
    • Year and Date
      2010-11-27
    • Related Report
      2011 Final Research Report
  • [Presentation] 結核菌の構成糖鎖を選択的に光分解する光感受性人工生体機能分子の創製2010

    • Author(s)
      高橋大介
    • Organizer
      GlycoTOKYO2010シンポジウム
    • Place of Presentation
      東京大学(本郷キャンパス、東京)
    • Year and Date
      2010-11-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] Target-selective photodegradation of oligosaccharides by light-activated small molecules2010

    • Author(s)
      D. Takahashi, S. Hirono, C. Hayashi, M. Igarashi, Y. Nishimura, K. Toshima
    • Organizer
      25^<th> International Carbohydrate Symposium
    • Place of Presentation
      Chiba
    • Year and Date
      2010-08-02
    • Related Report
      2011 Final Research Report
  • [Presentation] Target-selective Photodegradation of Oligosaccharides by Light-activated Small Molecules.2010

    • Author(s)
      高橋大介
    • Organizer
      25th International Carbohydrate Symposium
    • Place of Presentation
      幕張メッセ(千葉)
    • Year and Date
      2010-08-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] 標的糖鎖を選択的に光分解する生体機能分子の有機合成化学的創製~アントラキノン-ボロン酸ハイブリッドによる結核菌糖鎖の光分解~2010

    • Author(s)
      高橋大介、廣野信吾、戸嶋一敦
    • Organizer
      第97回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部芝共立キャンパス
    • Year and Date
      2010-06-18
    • Related Report
      2011 Final Research Report
  • [Presentation] 標的糖鎖を選択的に光分解する生体機能分子の有機合成化学的創製~アントラキノン-ボロン酸ハイブリッドによる結核菌糖鎖の光分解~2010

    • Author(s)
      高橋大介
    • Organizer
      第97回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学(芝共立キャンパス、東京)
    • Year and Date
      2010-06-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] アントラキノン-ボロン酸ハイブリッドによる標的糖鎖の選択的光分解と抗結核菌作用2010

    • Author(s)
      廣野信悟、林千草、五十嵐雅之、西村吉雄、高橋大介、戸嶋一敦
    • Organizer
      日本ケミカルバイオロジー学会第5回年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス
    • Year and Date
      2010-05-18
    • Related Report
      2011 Final Research Report
  • [Presentation] アントラキノン-ボロン酸ハイブリッドによる標的糖鎖の選択的光分解と抗結核菌作用2010

    • Author(s)
      廣野信悟
    • Organizer
      日本ケミカルバイオロジー学会 第5回年会
    • Place of Presentation
      慶應義塾大学(日吉キャンパス、神奈川)
    • Year and Date
      2010-05-18
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.applc.keio.ac.jp/~toshima/takahashi.html

    • Related Report
      2011 Annual Research Report

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Published: 2010-08-23   Modified: 2016-04-21  

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