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Synthesis of Cyclophane Oligomers Having Multivalently Enhanced Guest-Binding Affinity Based on Cluster Effect

Research Project

Project/Area Number 21550136
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionFukuoka University

Principal Investigator

HAYASHIDA Osamu  福岡大学, 理学部, 教授 (20231532)

Co-Investigator(Kenkyū-buntansha) ANDO Setsuko  福岡大学, 理学部, 講師 (20078562)
Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsホストゲスト化学 / シクロファン / クラスター効果 / ホストゲスト / 分子認識
Research Abstract

Water-soluble cyclophane dimer, trimer, tetramer, and pentamer were prepared by aminolysis of succinimidyl ester derivative of tetraaza[6.1.6.1] paracyclophane with lysine and the corresponding lysine peptide as a scaffold, followed by removal of the protecting groups. The present cyclophane oligomers showed enhanced guest-binding affinities toward fluorescent guests such as 6-p-toluidino-naphthalene-2-sulfonate, in comparison with those of monocyclic cyclophane, reflecting multivalency effects in macrocycles. The effects of multivalent macrocycles on the guest-binding of the present cyclophane oligomers were also confirmed by SPR measurements.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (17 results)

All 2012 2011 2010 2009

All Journal Article (9 results) (of which Peer Reviewed: 8 results) Presentation (8 results)

  • [Journal Article] Synthesis of peptide-based cyclophane oligomers having multivalently enhanced guest-binding affinity2012

    • Author(s)
      Osamu Hayashida, Tomomi Nakashima
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: (印刷中) Issue: 6 Pages: 715-723

    • DOI

      10.1246/bcsj.20120076

    • NAID

      130004059044

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of cyclophane dimer using cyclophane-tethered Fmoc-amino acid derivatives as a multivalent host2011

    • Author(s)
      Osamu Hayahsida, Tomomi Nakashima
    • Journal Title

      Chemistry Letters

      Volume: 40 Pages: 134-135

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Cyclophane Dimer Using Cyclophane-tethered Fmoc-Amino Acid Derivatives as a Multivalent Host2011

    • Author(s)
      Osamu Hayahsida
    • Journal Title

      Chemistry Letters

      Volume: 40 Pages: 134-135

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Surface plasmon resonance study on binding interactions of multivalent cyclophane hosts with immobilized guests2010

    • Author(s)
      Osamu Hayahsida, Daisuke Sato
    • Journal Title

      Polym. Adv. Technol

      Volume: 21 Pages: 96-99

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Guest-binding, cellular uptake, and molecular delivery of water-soluble cyclophanes having a pyrene moiety2010

    • Author(s)
      Osamu Hayahsida, Chika Eguchi, Keiichiro Kimura, Yu Oyama, Tomomi Nakashima, Kosei Shioji
    • Journal Title

      Chemistry Letters

      Volume: 39 Pages: 1321-1322

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Guest-binding, Cellular Uptake, and Molecular Delivery of Water-soluble Cyclophanes Having a Pyrene Moiety2010

    • Author(s)
      Osamu Hayahsida
    • Journal Title

      Chemistry Letters

      Volume: 39 Pages: 1321-1322

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Coordination Polymers of A Carboxylato Cyclophane with Metal[Zn(II)and Cd(II)]-2, 20-Bipyridines2010

    • Author(s)
      Osamu Hayahsida
    • Journal Title

      Polyhedron

      Volume: 29 Pages: 2755-2761

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Surface plasmon resonance study on binding interactions of multivalent cyclophane hosts with immobilized guests2010

    • Author(s)
      Osamu Hayahsida
    • Journal Title

      Polym.Adv.Technol. 21

      Pages: 96-99

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article]2009

    • Author(s)
      (監修)国武豊喜
    • Journal Title

      超分子サイエンス&テクノロジー(株式会社エヌ・ティー・エス)

      Pages: 83-94

    • Related Report
      2009 Annual Research Report
  • [Presentation] ペプチドを基本骨格としたシクロファン多量体の合成とゲスト捕捉能の比較評価2012

    • Author(s)
      中島智美・中村勇気・林田修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] ペプチドを基本骨格としたシクロファン多量体の合成とゲスト捕捉能の比較評価2012

    • Author(s)
      中島智美、中村勇気、林田修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜市
    • Related Report
      2011 Final Research Report
  • [Presentation] ペプチドを基本骨格としたシクロファンオリゴマーの合成とゲストとの結合親和性評価2011

    • Author(s)
      中島智美、中村勇気、林田修
    • Organizer
      第5回バイオ関連化学シンポジウム
    • Place of Presentation
      つくば市
    • Related Report
      2011 Final Research Report
  • [Presentation] Syntheses and guest-binding behaviors of peptide-based cyclophane oligomers2010

    • Author(s)
      Osamu Hayahsida
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ホノルル、アメリカ
    • Year and Date
      2010-12-17
    • Related Report
      2011 Final Research Report
  • [Presentation] Syntheses and guest-binding behaviors of peptide-based cyclophane oligomers2010

    • Author(s)
      Osamu Hayahsida
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ホノルル(アメリカ)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] ペプチドを基盤とするシクロファン多量体の合成とゲスト取り込みにおけるクラスター効果2010

    • Author(s)
      中島智美、中村勇気、林田修
    • Organizer
      第4回バイオ関連化学シンポジウム
    • Place of Presentation
      大阪市
    • Related Report
      2011 Final Research Report
  • [Presentation] Preparation and multivalently enhanced guest-binding affinity of peptide-based cyclophane oligomers2010

    • Author(s)
      Tomomi Nakashima, Osamu Hayashida
    • Organizer
      Fukuoka Univ. Ulsan Univ. Joint Seminar
    • Place of Presentation
      ウルサン、韓国
    • Related Report
      2011 Final Research Report
  • [Presentation] タンパク質の表面認識能を有するシクロファン集積型ホストの合成2009

    • Author(s)
      林田修
    • Organizer
      第24回生体機能関連化学シンポジウム
    • Place of Presentation
      九州大学
    • Year and Date
      2009-09-14
    • Related Report
      2009 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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