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Development of small thermodynamically stable NIR-II dyes, and their application as fluorescent probes.

Research Project

Project/Area Number 22K15259
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionUniversity of Toyama

Principal Investigator

Tanioka Masaru  富山大学, 学術研究部薬学・和漢系, 助教 (40846359)

Project Period (FY) 2022-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2023: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2022: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywords近赤外光 / キサンテン色素 / 架橋キサンテン色素 / 低分子量 / 熱力学的安定性 / 架橋フルオレセイン / 架橋ロドール / 無極性選択発光 / 光レドックス触媒反応 / 近赤外 / 光治療 / 近赤外蛍光 / NIR-II / 熱力学的安定 / 蛍光プローブ
Outline of Research at the Start

本研究は,波長 1000 nm ~ 1400 nm の第 2 近赤外光学窓領域で光吸収・蛍光を示す色素小分子(NIR-II 色素)をデザイン・創製し,蛍光プローブとして応用可能性を検討する。本研究の特徴は,申請者オリジナルの架橋キサンテン色素を分子デザイン・合成のプラットフォームとし,分子内の電荷を非局在化させることで,小さな分子サイズと熱力学的安定性を両立した新たな NIR-II 色素を創製することである。実験化学と計算化学を組み合わせた本研究は,小さな NIR-II 色素の設計指針の構築につながるとともに,医療・薬学分野および有機合成化学分野に資する機能性分子を提供する基盤研究となる。

Outline of Final Research Achievements

We developed small and thermodynamically stable near-infrared dyes based on "bridged xanthene dyes". Through this study, we succeeded in obtaining two new results, as described below. [1] We have clarified the synthetic method and optical properties of fluorescein-type bridged xanthene dyes (BFLs), and have succeeded in developing small-molecule NIR-I and -II dyes with less than 350 g/mol. [2] We discovered that rhodol-type bridged xanthene dyes (BRO) exhibit a new phenomenon called "non-polar selective emission (NPSE)," in which they emit light only in non-polar environments, and also found their potential as emission sensors and security inks.

Academic Significance and Societal Importance of the Research Achievements

「大きく・不安定であった」近赤外色素を「小さく・安定」にするための方法論は、新たな近赤外テクノロジーの開拓を可能にする点で材料化学分野に対して学術的意義を有する。また、本研究で発見した「無極性選択発光」現象は、新たな光物理現象として、光化学や理論化学分野の発展に資する。さらに、本研究で創出した色素を用いた水中での近赤外光レドックス触媒反応は、『生体の光レドックス治療』の第一歩と考えられるため、新たな光治療の創出に貢献する点で社会的な意義を有する。

Report

(3 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • Research Products

    (9 results)

All 2024 2023 2022

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 1 results) Presentation (4 results) (of which Invited: 1 results)

  • [Journal Article] Coerulein B: a water-soluble and water-compatible near-infrared photoredox catalyst2024

    • Author(s)
      Tanioka Masaru、Oyama Masaya、Nakajima Kaito、Mori Minori、Harada Mei、Matsuya Yuji、Kamino Shinichiro
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 26 Issue: 5 Pages: 4474-4479

    • DOI

      10.1039/d3cp05585j

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Controllable conformation and reactivity of bicyclic α-methylene cyclopentanones and their NF-κB pathway inhibitory activity2023

    • Author(s)
      Kohyama Aki、Shiuchi Aya、Zhou Yue、Tanioka Masaru、Sugimoto Kenji、Sakurai Hiroaki、Matsuya Yuji
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 21 Issue: 22 Pages: 4656-4660

    • DOI

      10.1039/d3ob00357d

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nucleophile‐Triggered π‐Topological Transformation: A New Synthetic Approach to Near‐Infrared‐Emissive Rhodamines2023

    • Author(s)
      Harada Mei、Kutsuna Misa、Kitamura Taichi、Usui Yusuke、Ujiki Masayoshi、Nakamura Yuka、Obata Tohru、Tanioka Masaru、Uchiyama Masanobu、Sawada Daisuke、Kamino Shinichiro
    • Journal Title

      Chemistry A European Journal

      Volume: 29 Issue: 59

    • DOI

      10.1002/chem.202301969

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bridged eosin Y: a visible and near-infrared photoredox catalyst2022

    • Author(s)
      Tanioka Masaru、Kuromiya Ayako、Ueda Rina、Obata Tohru、Muranaka Atsuya、Uchiyama Masanobu、Kamino Shinichiro
    • Journal Title

      Chemical Communications

      Volume: 58 Issue: 56 Pages: 7825-7828

    • DOI

      10.1039/d2cc02907c

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Visualization of the photodegradation of a therapeutic drug by chemometric-assisted fluorescence spectroscopy2022

    • Author(s)
      Tanioka Masaru、Ebihana Tsugumi、Uraguchi Manae、Shoji Haruka、Nakamura Yuka、Ueda Rina、Ogura Shota、Wakiya Yoshifumi、Obata Tohru、Ida Takahiro、Horigome Jun、Kamino Shinichiro
    • Journal Title

      RSC Advances

      Volume: 12 Issue: 32 Pages: 20714-20720

    • DOI

      10.1039/d2ra03534k

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] 近赤外光を利用可能な光レドックス触媒の開発2023

    • Author(s)
      〇谷岡卓
    • Organizer
      Toyama Academic GALA 2023
    • Related Report
      2023 Annual Research Report
  • [Presentation] フルオレセイン型色素の分子内架橋を鍵とする近赤外色素の合成と応用2023

    • Author(s)
      〇谷岡卓,尾山雅弥,松谷裕二
    • Organizer
      第49回反応と合成の進歩シンポジウム
    • Related Report
      2023 Annual Research Report
  • [Presentation] 近赤外光を利活用可能な分子の創出と光触媒への応用2022

    • Author(s)
      〇谷岡卓
    • Organizer
      令和4年度トメックス第20回研究会
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] 近赤外光物性を示す分子内架橋ロドールの合成と応用2022

    • Author(s)
      〇谷岡卓,清水璃音,中村あすか,森みのり,松谷裕二,神野伸一郎
    • Organizer
      2022年度北陸支部 第134回例会
    • Related Report
      2022 Research-status Report

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Published: 2022-04-19   Modified: 2025-01-30  

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