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Synthesis of high-valent metal porphyrins considering bacterial cell accumulation and the photobactericidal activity

Research Project

Project/Area Number 16K05847
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bio-related chemistry
Research InstitutionUniversity of Miyazaki

Principal Investigator

Matsumoto Jin  宮崎大学, 工学部, 准教授 (90363572)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords光増感剤 / ポルフィリン / 高原子価金属 / 光殺菌 / 光線力学療法
Outline of Final Research Achievements

We synthesized water-soluble P- and Sb-porphyrin complexes containing axial amphiphilic ligands, such as alkyl pyridimium moieties, in order to develop a photosensitizer for the photosterilization. The photobactericidal effects of the complexes were evaluated using nonpathogenic model cells, such as Saccharomyces cerevisiae and Escherichia coli. Optimization of the axial ligand by the introduction of appropriate alkyl groups improved the photobactericidal activities. Moreover, we succeeded in conversion of the complexes to the hydroporphyrin complexes with visible light absorption band at the longer wavelength in the phototherapeutic window. These complexes were exhibited to be promising as the photosensitizer for the photosterilization.

Academic Significance and Societal Importance of the Research Achievements

光増感剤と可視光照射による殺菌方法は、抗生物質を用いる殺菌方法と作用機構が異なるため、薬剤耐性菌を生まない利点を有する。ポルフィリン錯体の軸配位子を最適化する簡便な方法で、真菌やグラム陰性菌に対する殺菌活性を向上できることが示され、感染症治療にも有効な光増感剤が開発できたものと考えられる。また、酵母菌に対する光殺菌活性を有する錯体は、癌細胞にも光毒性を示すことから、がん治療を目的とする光線力学療法にも適用できるものと期待される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (26 results)

All 2019 2018 2017 2016

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 2 results) Presentation (17 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results) Book (2 results)

  • [Journal Article] Non-aggregated Porphyrins: An Approach to Develop High-performance PDT Sensitizers2018

    • Author(s)
      Matsumoto Jin、Yasuda Masahide
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 76 Issue: 6 Pages: 566-574

    • DOI

      10.5059/yukigoseikyokaishi.76.566

    • NAID

      130007384676

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2018-06-01
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and spectroscopic analysis of benzylidene imidazolone linked to P-porphyrins through axial ligand2018

    • Author(s)
      Matsumoto Jin、Takemori Kyosuke、Ishikawa Jun、Nabetani Yu、Fujitsuka Mamoru、Majima Tetsuro、Yasuda Masahide
    • Journal Title

      Medicinal Chemistry Research

      Volume: 27 Issue: 11-12 Pages: 2530-2537

    • DOI

      10.1007/s00044-018-2255-0

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Optimal axial alkylpyridinium-bonded tricationic P-porphyrin in photodynamic inactivation of Escherichia coli2018

    • Author(s)
      Jin Matsumoto, Masahide Yasuda
    • Journal Title

      Medicinal Chemistry Research

      Volume: 27 Issue: 5 Pages: 1478-1484

    • DOI

      10.1007/s00044-018-2166-0

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Additive effect of heparin on the photoinactivation of Escherichia coli using tricationic P-porphyrins2017

    • Author(s)
      Jin Matsumoto, Kou Suzuki, Hidekazu Uezono, Kaho Watanabe, Masahide Yasuda
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 27 Issue: 23 Pages: 5258-5261

    • DOI

      10.1016/j.bmcl.2017.10.032

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photodynamic therapy of human biliary cancer cell line using combination of phosphorus porphyrins and light emitting diode2017

    • Author(s)
      Jin Matsumoto, Kou Suzuki, Masahide Yasuda, Yuya Yamaguchi, Yoshitaka Hishikawa, Naoya Imamura, Atsushi Nanashima
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 25 Issue: 24 Pages: 6536-6541

    • DOI

      10.1016/j.bmc.2017.10.031

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Alkyl substituent effect on photosensitized inactivation of Escherichia coli2017

    • Author(s)
      J. Matsumoto, Y. Suemoto, H. Kanemaru, K. Takemori, M. Shigehara, A. Miyamoto, H. Yokoi, M. Yasuda
    • Journal Title

      Journal of Photochemistry & Photobiology, B: Biology

      Volume: 168 Pages: 124-131

    • DOI

      10.1016/j.jphotobiol.2017.02.001

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Assistance of human serum albumin to photo-sensitized inactivation of Saccharomyces cerevisiae with axially pyridinio-bonded P-porphyrins2016

    • Author(s)
      J. Matsumoto, Y. Kai, H. Yokoi, S. Okazaki, M. Yasuda
    • Journal Title

      Journal of Photochemistry & Photobiology, B: Biology

      Volume: 161 Pages: 279-283

    • DOI

      10.1016/j.jphotobiol.2016.05.024

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 菌体の光不活性化を目的とした水溶液リンポルフィリン錯体の開発2018

    • Author(s)
      松本 仁
    • Organizer
      第40回日本光医学・光生物学会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 軸配位アミノ基を有するリンポルフィリン錯体の蛍光特性 とそのpH 応答性2018

    • Author(s)
      上園 英知、松本 仁、白上 努
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] リンポルフィリン錯体への水素添加によるフロリンおよび クロリン錯体の合成とその光増感作用2018

    • Author(s)
      佐藤 加奈、松本 仁、白上 努
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 大腸菌の多価カチオンP-ポルフィリン増感不活性化に対するアルキル置換基効果2018

    • Author(s)
      渡辺 華帆、松本 仁、白上 努
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] P-ポルフィリン錯体による大腸菌の光不活性化に及ぼすアルキル基導入効果2018

    • Author(s)
      松本 仁、末元悠策、横井春比古、保田昌秀
    • Organizer
      第39回日本光医学・光生物学会
    • Related Report
      2017 Research-status Report
  • [Presentation] エチレングリコール型水溶性リンポルフィリン錯体の癌細胞における親和性と光線力学活性2018

    • Author(s)
      松本 仁、鈴木 巧、山口優也、菱川善隆、七島篤志、保田昌秀
    • Organizer
      第27回日本光線力学学会学術講演会
    • Related Report
      2017 Research-status Report
  • [Presentation] 軸配位子にフェニルボロン酸を有するSb ポルフィリン錯体の糖認識特性2018

    • Author(s)
      鈴木 巧、松本 仁、保田昌秀
    • Organizer
      2017年光化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 長波長域に吸収を有するフロリンへの金属導入による光安定化と光酸化活性2018

    • Author(s)
      繁原万里、松本 仁、保田昌秀
    • Organizer
      2017年光化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Photodynamic therapy of human biliary cancer cell using phosphorus porphyrins under irradiation with light emitting diode2018

    • Author(s)
      Kou Suzuki, Jin Matsumoto, Masahide Yasuda
    • Organizer
      2017 Korean-Japan Bilateral Symposium on Frontier Photoscience
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Photostability of phlorin metal complex and their photooxidation activity2018

    • Author(s)
      Masato Shigehara, Jin Matsumoto, Masahide Yasuda
    • Organizer
      2017 Korean-Japan Bilateral Symposium on Frontier Photoscience
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Kyosuke Takemori, Jin Matsumoto, Masahide Yasuda2018

    • Author(s)
      Synthesis and fluorescence properties of high-valent metal porphyrin complex with benzylidenimidazolone
    • Organizer
      2017 Korean-Japan Bilateral Symposium on Frontier Photoscience
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 生体親和性を考慮した水溶性高原子価金属ポルフィリン錯体の開発2017

    • Author(s)
      松本 仁
    • Organizer
      フォトダイナミックセラノスティクス研究会
    • Place of Presentation
      静岡大学浜松キャンパス
    • Year and Date
      2017-01-21
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 大腸菌のポルフィリン増感可視光殺菌に対するヘキシルピリジニウム置換基の効果2016

    • Author(s)
      末元悠策、松本 仁、横井春比古、保田昌秀
    • Organizer
      2016 年光化学討論会
    • Place of Presentation
      東京大学駒場第一キャンパス
    • Year and Date
      2016-09-06
    • Related Report
      2016 Research-status Report
  • [Presentation] 軸配位子にGFP発色団を有するSbポルフィリン錯体の合成と蛍光特性2016

    • Author(s)
      竹森恭佑、松本 仁、白上 努、保田昌秀
    • Organizer
      2016 年光化学討論会
    • Place of Presentation
      東京大学駒場第一キャンパス
    • Year and Date
      2016-09-06
    • Related Report
      2016 Research-status Report
  • [Presentation] カチオン性基の導入とHSA複合化によるポルフィリン増感可視光殺菌の高効率化2016

    • Author(s)
      松本 仁、白上 努、保田 昌秀
    • Organizer
      第38回日本光医学・光生物学会
    • Place of Presentation
      京都リサーチパーク サイエンスホール
    • Year and Date
      2016-07-22
    • Related Report
      2016 Research-status Report
  • [Presentation] 水溶性高原子価金属ポルフィリン錯体の合成と生体親和性評価2016

    • Author(s)
      松本 仁
    • Organizer
      第26回日本光線力学学会学術講演会
    • Place of Presentation
      はまぎんホール ヴィアマーレ
    • Year and Date
      2016-06-25
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis and spectroscopic properties of phosphorous hydroporphyrin complex with long-wavelength absorption bands2016

    • Author(s)
      J. Matsumoto, K. Tanimura, T. Shiragami, M. Yasuda
    • Organizer
      The 26th IUPAC Symposium on Photochemistry
    • Place of Presentation
      大阪市中央公会堂
    • Year and Date
      2016-04-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Book] Photodynamic Inactivation of Escherichia coli with Cationic Porphyrin Sensitizers2019

    • Author(s)
      Jin Matsumoto, Tomoko Matsumoto, Kazuya Yasuda, Masahide Yasuda (分担執筆)
    • Total Pages
      16
    • Publisher
      IntechOpen
    • Related Report
      2018 Annual Research Report
  • [Book] Silica Gel Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria2018

    • Author(s)
      Masahide Yasuda, Jin Matsumoto (分担執筆)
    • Total Pages
      17
    • Publisher
      IntechOpen
    • ISBN
      9781789230291
    • Related Report
      2018 Annual Research Report

URL: 

Published: 2016-04-21   Modified: 2020-03-30  

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