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Application of heteroatom-embedded porphyrins to photodynamic therapy

Research Project

Project/Area Number 19KK0138
Research Category

Fund for the Promotion of Joint International Research (Fostering Joint International Research (B))

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 33:Organic chemistry and related fields
Research InstitutionNagoya University

Principal Investigator

Shinokubo Hiroshi  名古屋大学, 工学研究科, 教授 (50281100)

Co-Investigator(Kenkyū-buntansha) 三宅 由寛  兵庫県立大学, 理学研究科, 教授 (00347270)
Shin Jiyoung  名古屋大学, 工学研究科(国際), 教授 (30622295)
福井 識人  名古屋大学, 工学研究科, 講師 (70823277)
Project Period (FY) 2019-10-07 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥18,330,000 (Direct Cost: ¥14,100,000、Indirect Cost: ¥4,230,000)
Fiscal Year 2021: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2020: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2019: ¥7,410,000 (Direct Cost: ¥5,700,000、Indirect Cost: ¥1,710,000)
Keywordsジアザポルフィリン / ヘテロ元素 / 光線力学的療法 / がん / 色素 / 一重項酸素 / 光線力学療法 / ポルフィリン / クロリン / がん細胞 / 近赤外
Outline of Research at the Start

光線力学療法(Photodynamic Therapy = PDT)とは、光励起による一重項酸素発生に基づく癌治療であり、低侵襲癌治療法として注目される。しかし、深部癌を治療するには生体透過性の高い近赤外光で励起できる増感剤を開発する必要がある。そこで本研究では、日本ー韓国ーフランスの三国間で国際共同研究を行い、ヘテロ元素を含む新規ポルフィリン誘導体を用いて高活性近赤外PDT光増感剤を開発することを目指す。

Outline of Final Research Achievements

Photodynamic therapy (PDT) is a non-invasive cancer treatment that employs photosensitizers and light to generate singlet oxygen. In this research, we elucidated that 5,15-diazaporphyrin appended with D-mannose moieties was sufficiently soluble in water and exhibited the strong PDT activity toward human breast adenocarcinoma at a nanomolar level with short light irradiation time.

Academic Significance and Societal Importance of the Research Achievements

光線力学療法(Photodynamic Therapy = PDT)とは、光増感による一重項酸素発生を利用する癌治療法である。正常な組織への影響が少ない低侵襲な癌治療法として実用化が進められている。本研究では、糖を導入したジアザポルフィリン色素が低濃度でヒトの乳がん細胞に対して優れたPDT活性を示すことを見い出した。この結果は、ヘテロ原子を含有するポルフィリン誘導体の光線力学療法における可能性を示すものである。

Report

(5 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (55 results)

All 2023 2022 2021 2020 2019 Other

All Int'l Joint Research (8 results) Journal Article (12 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 12 results) Presentation (29 results) (of which Int'l Joint Research: 7 results,  Invited: 8 results) Remarks (6 results)

  • [Int'l Joint Research] Montpellier University(フランス)

    • Related Report
      2022 Annual Research Report
  • [Int'l Joint Research] Yonsei University(韓国)

    • Related Report
      2022 Annual Research Report
  • [Int'l Joint Research] Montpellier University(フランス)

    • Related Report
      2021 Research-status Report
  • [Int'l Joint Research] Yonsei University(韓国)

    • Related Report
      2021 Research-status Report
  • [Int'l Joint Research] Yonsei University(韓国)

    • Related Report
      2020 Research-status Report
  • [Int'l Joint Research] University of Montpellier(フランス)

    • Related Report
      2020 Research-status Report
  • [Int'l Joint Research] モンペリエ大学(フランス)

    • Related Report
      2019 Research-status Report
  • [Int'l Joint Research] 延世大学(韓国)

    • Related Report
      2019 Research-status Report
  • [Journal Article] D-Mannose-appended 5,15-diazaporphyrin for photodynamic therapy2022

    • Author(s)
      Ali Lamiaa M. A.、Miyagawa Kazuya、Fukui Norihito、Onofre Melanie、El Cheikh Khaled、Morere Alain、Clement Sebastien、Gary-Bobo Magali、Richeter Sebastien、Shinokubo Hiroshi
    • Journal Title

      Organic Biomolecular Chemistry

      Volume: 20 Issue: 42 Pages: 8217-8222

    • DOI

      10.1039/d2ob01410f

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] 5-Thiaporphyrinium Cation: Effect of Sulphur Incorporation on Excited State Dynamics2022

    • Author(s)
      Takiguchi Aashi、Inai Naoto、Kang Seongsoo、Hagai Masaya、Lee Seokwon、Yanai Takeshi、Kim Dongho、Shinokubo Hiroshi
    • Journal Title

      Chemical Communications

      Volume: 58 Issue: 40 Pages: 5956-5959

    • DOI

      10.1039/d2cc00522k

    • Related Report
      2022 Annual Research Report 2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and Tautomerization of 5-Azaporphyrinium Cations2022

    • Author(s)
      Takiguchi Asahi、Shinokubo Hiroshi
    • Journal Title

      Chemistry Letters

      Volume: 51 Issue: 6 Pages: 590-593

    • DOI

      10.1246/cl.220122

    • Related Report
      2022 Annual Research Report 2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Nitrogen Extrusion of Diazacorrphycenes to Azacorroles and Synthesis of Two Types of Copper 10-Azacorrole Complexes2022

    • Author(s)
      Yagi Atsumi、Okada Naoya、Fukui Norihito、Tanaka Hisaaki、Hatakeyama Takuji、Shinokubo Hiroshi
    • Journal Title

      Chemistry Letters

      Volume: 51 Issue: 3 Pages: 321-324

    • DOI

      10.1246/cl.210777

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Diverse Crystal Structures of Ion Pairs Consisting of Oxaporphyrinium Cations and Pentacyanocyclopentadienide2022

    • Author(s)
      Takiguchi Asahi、Tanaka Hiroki、Maeda Hiromitsu、Shinokubo Hiroshi
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 95 Issue: 5 Pages: 796-801

    • DOI

      10.1246/bcsj.20220026

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Heme‐Acquisition Protein Reconstructed with a Cobalt 5‐Oxaporphyrinium Cation and Its Growth‐Inhibition Activity Toward Multidrug‐Resistant Pseudomonas aeruginosa2022

    • Author(s)
      Takiguchi Asahi、Sakakibara Erika、Sugimoto Hiroshi、Shoji Osami、Shinokubo Hiroshi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61 Issue: 7 Pages: 202112456-202112456

    • DOI

      10.1002/anie.202112456

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Antiaromatic 1,5‐Diaza‐s‐indacenes2021

    • Author(s)
      Hanida Kensuke、Kim Jinseok、Fukui Norihito、Tsutsui Yusuke、Seki Shu、Kim Dongho、Shinokubo Hiroshi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 38 Pages: 20765-20770

    • DOI

      10.1002/anie.202109003

    • NAID

      120007192017

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Dual Emission of a Free‐Base 5‐Oxaporphyrinium Cation from its cis‐ and trans‐NH Tautomers2020

    • Author(s)
      Takiguchi Asahi、Kang Seongsoo、Fukui Norihito、Kim Dongho、Shinokubo Hiroshi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 6 Pages: 2915-2919

    • DOI

      10.1002/anie.202013542

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Site-selective halogenation on meso-mesityl substituents of 10,20-dimesityl-5,15-diazaporphyrins with an AuX3/AgOTf combination2020

    • Author(s)
      Longevial Jean-Francois、Miyagawa Kazuya、Shinokubo Hiroshi
    • Journal Title

      Dalton Transactions

      Volume: 49 Issue: 42 Pages: 14786-14789

    • DOI

      10.1039/d0dt02727h

    • NAID

      120007145964

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] meso‐Diazacorrphycenes: Neighboring Effect of Two Nitrogen Atoms2020

    • Author(s)
      Yagi Atsumi、Shinokubo Hiroshi
    • Journal Title

      Chemistry A European Journal

      Volume: 26 Issue: 37 Pages: 8210-8213

    • DOI

      10.1002/chem.202002053

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and properties of 5-aza-15-thiaporphyrins2020

    • Author(s)
      Yamashita Daisuke、Omori Hiroto、Fukui Norihito、Shinokubo Hiroshi
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 24 Issue: 01n03 Pages: 84-89

    • DOI

      10.1142/s108842461950069x

    • NAID

      120006848966

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Site‐Selective N‐Methylation of 5,15‐Diazaporphyrins: Reactive Cationic Porphyrinoids that Provide Isoporphyrin Analogues2020

    • Author(s)
      Chia Wen Xi、Nishijo Mayu、Kang Seongsoo、Oh Juwon、Nishimura Tsubasa、Omori Hiroto、Longevial Jean‐Fran?ois、Miyake Yoshihiro、Kim Dongho、Shinokubo Hiroshi
    • Journal Title

      Chemistry European Journal

      Volume: 26 Issue: 12 Pages: 2754-2760

    • DOI

      10.1002/chem.201905402

    • NAID

      120006848960

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] 水素結合を利用した5,15-ジアザポルフィリンの構造制御2023

    • Author(s)
      櫻井貴浩,森しほ,西村翼,三宅由寛,忍久保洋
    • Organizer
      日本化学会第103回春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 10-プラチナコロールの合成と物性2023

    • Author(s)
      三輪一樹,櫻井貴浩, 横田智也, 忍久保洋
    • Organizer
      日本化学会第103回春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] meso 位にエステル基をもつジピリン錯体からのポルフィリノイ ド合成2023

    • Author(s)
      平松 永伍、木野 翔太、劉 思雨、忍久保 洋
    • Organizer
      日本化学会第103回春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 反芳香族化合物の近接積層2022

    • Author(s)
      忍久保 洋
    • Organizer
      第16回物性科学領域横断研究会
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] プラチナコロールの合成と物性2022

    • Author(s)
      三輪一樹,横田智也,忍久保洋
    • Organizer
      第53回中部化学関係学協会支部連合秋季大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] ポルフィリンのちょい足しとちょい引きの化学:芳香族性をひっくり返す2022

    • Author(s)
      忍久保 洋
    • Organizer
      CSJ化学フェスタ2022
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] 反芳香族ポルフィリン:ノルコロールの化学2022

    • Author(s)
      忍久保 洋
    • Organizer
      化学部門特別講演会, 北海道大学
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] Switching off antiaromaticity by stacking: close stacking of norcorroles2022

    • Author(s)
      忍久保 洋
    • Organizer
      Lecture at Hunan Normal University
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] プラチナコロールの合成と物性2022

    • Author(s)
      三輪一樹・横田智也・忍久保 洋
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] ジアザゼトレンビスイミドの反応性と光物性2022

    • Author(s)
      田島慶太,福井識人,忍久保洋
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 外周部に金属配位したテトラピリジルジアザポルフィリンパラジウム錯体の 還元挙動と芳香族性2022

    • Author(s)
      櫻井貴浩,三宅由寛,忍久保洋
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Synthesis and Properties of Outer-Palladated Tetrapyridyldiazaporphyrin Complexes2022

    • Author(s)
      櫻井貴浩,三宅由寛,忍久保洋
    • Organizer
      11th International Conference on Porphyrins and Phthalocyanines (ICPP-11)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Close stacking of antiaromatic norcorrole complexes2022

    • Author(s)
      忍久保 洋
    • Organizer
      19th International Symposium on Novel Aromatic Compounds (ISNA 19)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 反芳香族ポルフィリン:ノルコロールの化学2022

    • Author(s)
      忍久保 洋
    • Organizer
      大阪公立大学大学院工学研究科講演会
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] 外周部に金属配位したテトラピリジルジアザポルフィリンパラジウム錯体の合成と物性2022

    • Author(s)
      櫻井 貴浩, 三宅 由寛, 忍久保 洋
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] テトラブロモジピリンを基盤とするβ位修飾ジアザポルフィリンの合成2021

    • Author(s)
      櫻井貴浩,西村翼, 三宅由寛,忍久保洋
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] オキサポルフィリニウムカチオンの構造・物性と生物活性2021

    • Author(s)
      瀧口 あさひ、榊原 えりか、杉本 宏、荘司 長三、忍久保 洋
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] Facile Synthesis of Bilindione and Optical Property of 5-Oxaporphyrinium Cation2021

    • Author(s)
      瀧口 あさひ, Seongsoo Kang, 福井 識人, Dongho Kim, 忍久保 洋
    • Organizer
      11th International Conference on Porphyrins and Phthalocyanines (ICPP-11)
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Property of 14,15-Diazacorrphycene Palladium Complex2021

    • Author(s)
      八木 篤実, 忍久保 洋
    • Organizer
      11th International Conference on Porphyrins and Phthalocyanines (ICPP-11)
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Redox-Induced Reversible [2+2] Cycloaddition of Etheno-Fused Diporphyrin2021

    • Author(s)
      宮川 和弥, 福井 識人, 忍久保 洋
    • Organizer
      11th International Conference on Porphyrins and Phthalocyanines (ICPP-11)
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] ビリンジオンの簡易合成法と5-オキサポルフィリニウムカチオンの光学特性2021

    • Author(s)
      Asahi Takiguchi, Seongsoo Kang, Norihito Fukui, Dongho Kim, Hiroshi Shinokubo
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] アザインドール骨格をもつオクタアザ[8]サーキュレンの合成とそのプロトン化挙動2021

    • Author(s)
      Shuhei Akahori, Hiroshi Shinokubo, Yoshihiro Miyake
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] Synthesis and Properties of 5-Oxaporphyrinium Cation and Its Application2021

    • Author(s)
      Asahi Takiguchi, Norihito Fukui, Hiroshi Shinokubo
    • Organizer
      GTR年次報告会
    • Related Report
      2020 Research-status Report
  • [Presentation] Synthesis and Property of 14,15-Diazacorrphycene Metal Complex2021

    • Author(s)
      Atsumi Yagi, Hiroshi Shinokubo
    • Organizer
      GTR年次報告会
    • Related Report
      2020 Research-status Report
  • [Presentation] ジアザ-s-インダセンの合成と物性2020

    • Author(s)
      Kensuke Hanida, Norihito Fukui, Hiroshi Shinokubo
    • Organizer
      若手オンラインシンポジウム
    • Related Report
      2020 Research-status Report
  • [Presentation] 14,15-ジアザコルフィセンパラジウム錯体の合成と物性2020

    • Author(s)
      八木 篤実
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Fusion of Porphyrin Chemistry and Organic Chemistry2020

    • Author(s)
      Hiroshi Shinokubo
    • Organizer
      Commemorative symposium in Kyoto on the retirement of Prof. Atsuhiro Osuka
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ジアザコルフィセンの合成と物性2019

    • Author(s)
      八木 篤実
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] ヘテロ元素含有ポルフィリンの合成と その機能探索2019

    • Author(s)
      忍久保 洋
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Remarks] 忍久保研究室ホームページ

    • URL

      http://www.chembio.nagoya-u.ac.jp/labhp/organic1/index.html

    • Related Report
      2022 Annual Research Report 2021 Research-status Report 2020 Research-status Report
  • [Remarks] Dongho Kim Group

    • URL

      https://www.fpieslab.com/

    • Related Report
      2020 Research-status Report
  • [Remarks] Institut Charles Gerhardt Montpellier

    • URL

      https://www.icgm.fr/sebastien-richeter

    • Related Report
      2020 Research-status Report
  • [Remarks] Institut des Biomolécules Max Mousseron

    • URL

      https://ibmm.umontpellier.fr/spip.php?page=pageperso&id_user=366&lang=fr

    • Related Report
      2020 Research-status Report
  • [Remarks] 有機合成で拓く新しい分子の世界

    • URL

      http://www.chembio.nagoya-u.ac.jp/labhp/organic1/research.html

    • Related Report
      2019 Research-status Report
  • [Remarks] Sebastien Richeter

    • URL

      https://www.icgm.fr/sebastien-richeter

    • Related Report
      2019 Research-status Report

URL: 

Published: 2019-10-10   Modified: 2024-01-30  

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