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Development and Application of Blue-Light-Emitting Fluorophores Extremely Stable to Ultraviolet Excitation

Research Project

Project/Area Number 15K13667
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionUniversity of Toyama

Principal Investigator

Inouye Masahiko  富山大学, 大学院医学薬学研究部(薬学), 教授 (60211752)

Co-Investigator(Renkei-kenkyūsha) FUJIMOTO Kazuhisa  九州産業大学, 工学部, 准教授 (40334718)
Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsロタキサン / 蛍光色素 / 高光耐久性 / バイオプローブ / 光安定性 / シクロデキストリン / 一重項酸素
Outline of Final Research Achievements

We have developed [3]rotaxane-type fluorophores, in which an alkynylpyrene is encapsulated with two permethyl α -cyclodextrins (PM α-CD). Conclusive proof for the [3]rotaxane structure was obtained on the basis of its X-ray structure analysis. This fluorophore showed extremely high photo-stability because PM α-CD, like bulletproof glass, protected the alkynylpyrene core from the attack of reactive species. Fluorescence spectrum measurement revealed that the [3]rotaxane-type alkynylpyrene emitted only blue light of monomeric pyrene in the various circumstances such as lipophilic, hydrophilic, and even condensed states.
Aiming at evolution of the rotaxane-type fluorophore to biomolecule-labeling agents, we synthesized new [3]rotaxane-type alkynylpyrens with succinimidyl ester. After labeling the protein with this rotaxane, photo-bleaching experiment was executed. It was found that the extremely high photostability of the rotaxane is maintained even after labeling the protein.

Report

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

    (11 results)

All 2017 2016 2015

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 1 results) Presentation (6 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Kinetic Switching of Achirality/Chirality Memorization of meta-Ethynylpyridine Polymer by Coordination of Cu(II) Outside the Polymer2017

    • Author(s)
      H. Abe, S. Takashima, M. Inouye
    • Journal Title

      Heterocycles

      Volume: 印刷中 Issue: 2 Pages: 730-730

    • DOI

      10.3987/com-16-s(s)64

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Helix-Rotaxane Hybrid Systems: Rotaxane-Stabilized, Saccharide-Induced Chiral Ethynylpyridine Helices by a Thermodynamic Process2017

    • Author(s)
      S. Hirokane, S. Takashima, H. Abe, M. Inouye
    • Journal Title

      Eur. J. Org. Chem.

      Volume: - Issue: 3 Pages: 726-733

    • DOI

      10.1002/ejoc.201601323

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A D3h-Symmetric Macrocycle Alternatingly Composed of Pyridine and Benzyl Alcohol Units Linked with Acetylene Bonds2016

    • Author(s)
      H. Abe, R. Yumoto, M. Inouye
    • Journal Title

      Heterocycles

      Volume: 93 Issue: 2 Pages: 580-592

    • DOI

      10.3987/com-15-s(t)44

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] D3h-Symmetrical Shape-Persistent Macrocycles Consisting of Pyridine-Acetylene-Phenol Conjugates as a Highly Efficient Host Architecture for Saccharide Recognition2016

    • Author(s)
      H. Abe, T. Yoneda, Y. Ohishi, M. Inouye
    • Journal Title

      Chem.-Eur. J.

      Volume: 22 Issue: 52 Pages: 18944-18952

    • DOI

      10.1002/chem.201603987

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cyclodextrin-Isolated Alkynylpyrenes as UV-Stable and Blue-Light-Emitting Molecules Even in Condensed States2016

    • Author(s)
      5.M. Inouye, A. Yoshizawa, M. Shibata, Y. Yonenaga, K. Fujimoto, T. Sakata, S. Matsumoto, M. Shiro
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 9 Pages: 1960-1963

    • DOI

      10.1021/acs.orglett.6b00420

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 短波長励起光に安定なロタキサン型ビスフェニルエチニルピレンの生体分子標識への応用2017

    • Author(s)
      由澤敦史・井上将彦
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-15
    • Related Report
      2016 Annual Research Report
  • [Presentation] テンプレートクリック法による青色発光を示すアルキニルピレン型ロタキサンの合成2017

    • Author(s)
      菅原颯馬・林滉一朗・由澤敦史・井上将彦
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-15
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of [3]Rotaxane-type Bis(phenylethynyl)pyrenes and Their Application to Biomolecular Labeling2017

    • Author(s)
      由澤敦史・井上将彦
    • Organizer
      感応性化学種が拓く新物質科学 第2回国際シンポジウム
    • Place of Presentation
      東広島
    • Year and Date
      2017-03-06
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 高い紫外光耐久性と環境非依存的発光特性を示す[3]ロタキサン型アルキニルピレンの開発2016

    • Author(s)
      由澤敦史、藤本和久、佐方拓馬、松本慎哉、城始勇、井上将彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 分子レベルでの被覆を利用した高光安定性ロタキサン型アルキニルピレンの開発2015

    • Author(s)
      由澤敦史、伊藤達哉、藤本和久、佐方拓馬、松本慎哉、城始勇、井上将彦
    • Organizer
      第16回リングチューブ研究会シンポジウム
    • Place of Presentation
      つくば
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 環境非応答的にモノマー発光のみを示す高光安定性ロタキサン型アルキニルピレンの開発2015

    • Author(s)
      由澤敦史、伊藤達哉、藤本和久、井上将彦
    • Organizer
      第13回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2015-06-06
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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