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Design and Synthesis of Caged Compound with High Two-Photon Absorption Character in Near IR Region :Its Application to Physiological Experiments

Research Project

Project/Area Number 21K20539
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeMulti-year Fund
Review Section 0501:Physical chemistry, functional solid state chemistry, organic chemistry, polymers, organic materials, biomolecular chemistry, and related fields
Research InstitutionKyushu University (2022)
Hiroshima University (2021)

Principal Investigator

Chitose Youhei  九州大学, 工学研究院, 助教 (60911534)

Project Period (FY) 2021-08-30 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Fiscal Year 2022: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2021: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords2光子吸収 / ケージド化合物 / 光解離性保護基 / 反応中間体 / D-π-D / 安息香酸 / 生物活性物質 / 励起状態
Outline of Research at the Start

本研究では,理論計算によって高い近赤外2光子吸収能を有する光解離性保護基を設計し,合成を行う.有機溶媒中での光脱保護効率を確認したのち,保護基部位に十分な水溶性を有する置換基を導入することで細胞実験への応用を試みる.グルタミン酸や抗がん剤などの生物活性物質を保護したケージド化合物を合成し,生体内において,近赤外光を用いて活性物質の濃度上昇を時空間的に制御し,これまで未知であった活性発現機構の解明に貢献する.

Outline of Final Research Achievements

In this study, we developed a Donor-π-Donor (D-π-D) based coumarin derivative. Its two-photon absorption (TPA) cross-section was determined to be 498 GM at 700 nm by two-photon excited fluorescence method. The two-photon uncaging efficiency of D-π-D based caged benzoic acid was also determined to be 134 GM at 700 nm, which indicates relatively high two-photon responsive chromophore. In addition, we investigated the detail mechanism of bond cleavage steps in the uncaging reaction of caged benzoic acid. The laser flash photolysis experiments and product analysis suggested the presence of methyl cation intermediate which indicated the heterolysis of C-O bond.

Academic Significance and Societal Importance of the Research Achievements

既存の7-ジエチルアミノクマリン骨格の3位に2重結合を持つ電子供与基部位を導入することで、比較的高い2光子吸収断面積を付与することができた。今後、D-π-D型クマリン誘導体を基盤骨格とする光解離性保護基を用いたケージド化合物を開発することで、低毒性かつ生体透過性の高い近赤外領域の2光子励起を用いて生物活性物質の濃度上昇を時空間的に制御することができる。こうした技術を応用することによって、生体深部における疾患部位の回復や、脳内における神経伝達物質の機能解明に繋がると期待される。

Report

(3 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • Research Products

    (6 results)

All 2022 2021

All Journal Article (3 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 3 results,  Open Access: 1 results) Presentation (3 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Assemblies of 1,4-Bis(diarylamino)naphthalene and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water2022

    • Author(s)
      Yuki Hyodo, Keigo Takahashi, Youhei Chitose, Manabu Abe, Michito Yoshizawa, Takashi Koike, Munetaka Akita
    • Journal Title

      Synlett

      Volume: 33 Issue: 12 Pages: 1184-1188

    • DOI

      10.1055/a-1652-2707

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins2021

    • Author(s)
      Morofuji Tatsuya、Nagai Shota、Chitose Youhei、Abe Manabu、Kano Naokazu
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 16 Pages: 6257-6261

    • DOI

      10.1021/acs.orglett.1c02026

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Impact of Five-membered Heterocyclic Rings on Photophysical Properties Including Two-photon Absorption Character2021

    • Author(s)
      Pham Thuy Thi Thu、Chitose Youhei、Tam Tran Thi Thanh、Tseng Wei-Lun、Lin Tzu-Chau、Abe Manabu
    • Journal Title

      Chemistry Letters

      Volume: 50 Issue: 10 Pages: 1810-1813

    • DOI

      10.1246/cl.210420

    • NAID

      130008101919

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] Design, Synthesis, and Photoreactions of Near Infrared Two-photon Responsive Caged Compounds Bearing Coumarin Scaffold2021

    • Author(s)
      Youhei Chitose, Manabu Abe, Tzu-Chau Lin, Claudine Katan
    • Organizer
      Joint Symposium between CSIR-CDRI and HiU-P-DDS
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] 近赤外二光子吸収能を有するケージド化合物の設計,合成,光反応2021

    • Author(s)
      千歳 洋平, 安倍 学, 林 子超, クラウディン カタン
    • Organizer
      第10回JACI/GSCシンポジウム
    • Related Report
      2021 Research-status Report
  • [Presentation] D-π-D 構造を有する近赤外二光子応答性クマリン型ケージド化合物の設計、合成、光反応2021

    • Author(s)
      千歳 洋平, 安倍 学, 林 子超, クラウディン カタン
    • Organizer
      第37回有機合成化学セミナー
    • Related Report
      2021 Research-status Report

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Published: 2021-10-22   Modified: 2024-01-30  

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