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Synthesis of stimuli-responsive cyclophane oligomers for controlled catch and release of guest molecules

Research Project

Project/Area Number 24550166
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
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)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2012: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsシクロファン / ホストゲスト化学 / 還元応答性 / 分子認識化学 / クラスター効果 / 刺激応答
Outline of Final Research Achievements

In order to enhance guest-binding affinities, water-soluble cyclophane oligomers was synthesized by click chemistry. The present cyclophane oligomers demonstrated enhanced guest-binding affinities toward fluorescent guests such as 6-p-toluidinonaphthalene- 2-sulfonate, in comparison with those of monomeric cyclophane, reflecting multivalency effects in macrocycles. In addition, water-soluble anionic cyclophane having diphenyl disulfide moieties was also synthesized as a reduction-responsive degradable host. The anionic cyclophane binds cationic anticancer drugs such as daunorubicin hydrochloride (DNR). Reduction of disulfide bonds of the host by dithiothreitol gave its reduced form having poor guest-binding affinity that led to release of the entrapped guest molecules to the bulk aqueous phase.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (27 results)

All 2015 2014 2013 2012 Other

All Journal Article (13 results) (of which Peer Reviewed: 11 results,  Acknowledgement Compliant: 3 results) Presentation (13 results) (of which Invited: 1 results) Book (1 results)

  • [Journal Article] Entrapment and Release of Guest Molecules by Reduction-Responsive Cyclophane Dimers Based on Disulfide Linkage2015

    • Author(s)
      Osamu Hayashida*, Keiko Kojima
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 88 Issue: 5 Pages: 729-735

    • DOI

      10.1246/bcsj.20140370

    • NAID

      130005069505

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of A Rhodamine-Appended Cyclophane as A Fluorescence Host in Water2014

    • Author(s)
      Osamu Hayashida*, Yu Kaku,
    • Journal Title

      Adv. Chem. Eng. Sci.

      Volume: 4 Issue: 04 Pages: 401-408

    • DOI

      10.4236/aces.2014.44044

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Guest-Binding Behavior of Water-Soluble Cyclophanes Bearing PEG Residues2014

    • Author(s)
      Osamu Hayashida*, Yuki Nakamura, Takuya Sato
    • Journal Title

      Adv. Chem. Eng. Sci.

      Volume: 4 Issue: 04 Pages: 409-416

    • DOI

      10.4236/aces.2014.44045

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Degradation Properties and pH-Responsive Guest-Release of Cyclophanes Having Four Ester Side Chains with Terminal Choline Residues2014

    • Author(s)
      Osamu Hayashida*, Daisuke Sato
    • Journal Title

      Chem. Lett

      Volume: 43 Pages: 322-324

    • NAID

      130004868009

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Guest-Binding, and Reduction-Responsive Degradation Properties of Water-Soluble Cyclophanes Having Disulfide Moieties2013

    • Author(s)
      Osamu Hayashida, Kazuaki Ichimura, Daisuke Sato, Terutaka Yasunaga
    • Journal Title

      J. Org. Chem.

      Volume: 78 Issue: 11 Pages: 5463-5469

    • DOI

      10.1021/jo400591w

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Dabsyl-Appended Cyclophanes and Their Heterodimer Formation with Pyrene-Appended Cyclophanes2013

    • Author(s)
      Osamu Hayashida, Yu Kaku
    • Journal Title

      J. Org. Chem

      Volume: 78 Issue: 20 Pages: 10437-10442

    • DOI

      10.1021/jo4018843

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] クラスター効果によって機能化された水溶性 シクロファン類の創製とゲスト捕捉能2013

    • Author(s)
      林田 修、市村 和明、木村 圭一朗、中村 勇気、中島 智美
    • Journal Title

      福岡大学理学集報

      Volume: 43 Pages: 87-95

    • NAID

      110009558621

    • Related Report
      2013 Research-status Report
  • [Journal Article] 機能性ナノ分子研究2013

    • Author(s)
      林田 修、松原 公紀、安東 勢津子、古賀 裕二
    • Journal Title

      Research

      Volume: 18 Pages: 36-37

    • Related Report
      2013 Research-status Report
  • [Journal Article] Synthesis of Water-Soluble Cyclophane Pentamers Using Click Chemistry as a Multivalent Host for Daunorubicin and Doxorubicin2013

    • Author(s)
      O. Hayashida, Y. Nakamura
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 86 Issue: 2 Pages: 223-229

    • DOI

      10.1246/bcsj.20120296

    • NAID

      10031155743

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] 林田 修、市村 和明、木村 圭一朗、中村 勇気、中島 智美2013

    • Author(s)
      クラスター効果によって機能化された水溶性 シクロファン類の創製とゲスト捕捉能
    • Journal Title

      福岡大学理学集報

      Volume: 43 Pages: 87-95

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and enhanced guest-binding affinities of dendrimer-based cyclophane tetramer and octamer2013

    • Author(s)
      O. Hayashida, Y. Nakamura, Y. Kaku
    • Journal Title

      Adv. Chem. Eng. Sci.

      Volume: 3

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [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
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and characterization of reduction- responsive cyclophane dimer based on disulfide linkage2012

    • Author(s)
      O. Hayashida, K. Ichimura
    • Journal Title

      Chem. Lett.

      Volume: 41 Issue: 12 Pages: 1650-1651

    • DOI

      10.1246/cl.2012.1650

    • NAID

      10031135781

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 動的共有結合を有する水溶性シクロファン多量体の合成とゲスト捕捉能の制御2014

    • Author(s)
      大野 達矢・松下 幸司・林田 修
    • Organizer
      第8回バイオ関連化学シンポジウム2014
    • Place of Presentation
      岡山大学津島キャンパス
    • Year and Date
      2014-09-11 – 2014-09-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] シスチンで連結したシクロファン2量体の合成と還元応答性2014

    • Author(s)
      小島 恵子・中村 湧・林田 修
    • Organizer
      第8回バイオ関連化学シンポジウム2014
    • Place of Presentation
      岡山大学津島キャンパス
    • Year and Date
      2014-09-11 – 2014-09-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] シクロファン多量体の合成とゲスト捕捉能の制御2014

    • Author(s)
      中村 湧・小島 恵子・林田 修
    • Organizer
      第8回バイオ関連化学シンポジウム2014
    • Place of Presentation
      岡山大学津島キャンパス
    • Year and Date
      2014-09-11 – 2014-09-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] オキシエチレン基で連結したシクロファン2量体の合成と機能2014

    • Author(s)
      松下 幸司・大野 達矢・林田 修
    • Organizer
      第8回バイオ関連化学シンポジウム2014
    • Place of Presentation
      岡山大学津島キャンパス
    • Year and Date
      2014-09-11 – 2014-09-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] ジスルフィド結合で連結したシクロファン5量体の合成と性質2014

    • Author(s)
      中村 湧・林田 修
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 種々のスペーサーで連結したシクロファン2量体の合成とホスト機能2014

    • Author(s)
      松下 幸司・大野 達矢・林田 修
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ローダミン部位を有するシクロファンの合成と細胞内ゲスト送達2014

    • Author(s)
      加來 悠・小島 恵子・林田 修
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] シスチンで連結した蛍光性シクロファン2量体の合成と機能2013

    • Author(s)
      小島 恵子・加來 悠・林田 修
    • Organizer
      第7回バイオ関連化学シンポジウム
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 蛍光消光法によるシクロファンの細胞内取り込みとゲスト送達の評価2012

    • Author(s)
      加來 悠、木村 圭一朗、林田 修
    • Organizer
      第6回バイオ関連化学シンポジウム
    • Place of Presentation
      北海道大学
    • Related Report
      2012 Research-status Report
  • [Presentation] ジスルフィド結合を環骨格に組み込んだシクロファンの合成と 還元応答によるゲスト捕捉の制御2012

    • Author(s)
      市村 和明、林田 修
    • Organizer
      第6回バイオ関連化学シンポジウム
    • Place of Presentation
      北海道大学
    • Related Report
      2012 Research-status Report
  • [Presentation] SPR and Fluorescence Study on Host-guest Interactions of Cyclophane Oligomers Having Multivalently Enhanced Guest-binding Affinity2012

    • Author(s)
      O. Hayashida, K. Ichimura, K. Kimura, Y. Nakamura, T. Nakashima
    • Organizer
      Label-Free Technologies: Advances and Applications
    • Place of Presentation
      NH Grand Krasnapolsky, Amsterdam, The Netherlands
    • Related Report
      2012 Research-status Report
  • [Presentation] ジスルフィド部位を有する水溶性シクロファンの合成と分子認識

    • Author(s)
      市村和明、林田修
    • 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 Research-status Report
  • [Presentation] シクロファン多量体を用いたアニオン性ゲストのHepG2 細胞内取り込み

    • Author(s)
      木村 圭一朗、塩路 幸生、林田 修
    • Organizer
      第24回若手研究者のためのセミナー
    • Place of Presentation
      九州大学
    • Related Report
      2012 Research-status Report
    • Invited
  • [Book] 薬物送達のためのホストゲスト分子システムの構築2015

    • Author(s)
      林田 修
    • Total Pages
      3
    • Publisher
      福岡大学理学集報
    • Related Report
      2014 Annual Research Report

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Published: 2013-05-31   Modified: 2019-07-29  

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