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Development of antibody-near-infrared dye complexes for deep cancer treatment

Research Project

Project/Area Number 21K18984
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 34:Inorganic/coordination chemistry, analytical chemistry, and related fields
Research InstitutionRitsumeikan University (2022-2023)
Kyushu University (2021)

Principal Investigator

Furuta Hiroyuki  立命館大学, 総合科学技術研究機構, 教授 (40244157)

Co-Investigator(Kenkyū-buntansha) 石田 真敏  東京都立大学, 理学研究科, 准教授 (60706951)
Project Period (FY) 2021-07-09 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2022: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2021: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Keywords近赤外色素 / ポルフィリノイド / 第二近赤外 / 光免疫治療 / 抗体 / ポルフィリン / ヘキサフィリン / 近赤外光 / 光アンケージ
Outline of Research at the Start

がん治療において、患者への副作用の少ない治療法が求められており、近年、近赤外光免疫治療法と呼ばれる抗体と光感受性色素が複合化した薬剤の光反応性を利用してがん細胞のみを選択的に治療する本手法が注目を集めている。本研究では、照射光の細胞透過性を改善するために、より低エネルギー光感受性色素を開発し、深部がんの低侵襲的治療を目指した複合薬剤の開発を推進し、次世代光免疫治療法の確立を目指す。

Outline of Final Research Achievements

For developing the near-infrared light-sensitive drugs indispensable for near-infrared photoimmunotherapy, chemically stable near-infrared dyes incredibly responsible for the second near-infrared (NIR-II) light in the range of 1000 to 1400 nm has been demanded. Here, we conducted research aimed at creating dyes based on oligopyrroles, N-confused porphyrins, N-fused porphyrins, and ring-expanded porphyrins (sapphyrin, rosarin, hexaphyrin), including their dimers and metal complexes, and the optical properties were investigated. Platinum and palladium metal complexes of acyclic tetrapyrroles showed high photothermal conversion efficiency of over 60%. We conclude the introduction of confused pyrroles and metal complexation is a promising approach for designing dyes that respond to the NIR-II region.

Academic Significance and Societal Importance of the Research Achievements

一般に近赤外光に応答する分子は拡張したπ共役骨格を有することから高いHOMOレベルと低いLUMOレベルを示し、酸化還元活性である。そのため、化学的安定性の確保や高効率の近赤外光応答には、分子骨格に関する幅広い検討が求められる。我々は、構造修飾が容易でチューニング性の高いポルフィリン類縁体化合物、その中でもN―混乱ポルフィリン誘導体およびその金属錯体を用いた各種の分光学測定や光熱変換実験などから、その可能性があることを実証した。この結果は、近年注目されている近赤外光免疫治療法には欠かせない近赤外光感受性薬剤開発に対する重要な分子設計指針となる事が期待される。

Report

(3 results)
  • 2023 Final Research Report ( PDF )
  • 2022 Research-status Report
  • 2021 Research-status Report
  • Research Products

    (44 results)

All 2023 2022 2021 Other

All Int'l Joint Research (5 results) Journal Article (13 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 13 results,  Open Access: 4 results) Presentation (26 results) (of which Int'l Joint Research: 5 results,  Invited: 4 results)

  • [Int'l Joint Research] University of Wroclaw(ポーランド)

    • Related Report
      2022 Research-status Report
  • [Int'l Joint Research] ECUST(中国)

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

    • Related Report
      2021 Research-status Report
  • [Int'l Joint Research] GITAM(インド)

    • Related Report
      2021 Research-status Report
  • [Int'l Joint Research] University of Southern Denmark(デンマーク)

    • Related Report
      2021 Research-status Report
  • [Journal Article] Conformation-dependent photophysical properties of butadiyne-linked π-extended BODIPY dimers2023

    • Author(s)
      Sato Yuma、Shimada Takahide、Mori Shigeki、Yasutake Yuhsuke、Fukatsu Susumu、Furuta Hiroyuki、Ishida Masatoshi
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 27 Issue: 01n04 Pages: 486-492

    • DOI

      10.1142/s1088424623500232

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Redox properties of bis-cobalt(III) complex of 3,3′-linked N-confused porphyrin dimer with axial pyridine ligands2023

    • Author(s)
      Iwanaga Osamu、Yoshida Naoya、Miyazaki Takaaki、Tani Fumito、Mori Shigeki、Shimizu Soji、Ishida Masatoshi、Furuta Hiroyuki
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 27 Issue: 07n10 Pages: 1074-1082

    • DOI

      10.1142/s1088424623500281

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Organometallic chemistry confined within a porphyrin-like framework2023

    • Author(s)
      Bialek Michal J.、Hurej Karolina、Furuta Hiroyuki、Latos-Grazynski Lechoslaw
    • Journal Title

      Chemical Society Reviews

      Volume: 52 Issue: 6 Pages: 2082-2144

    • DOI

      10.1039/d2cs00784c

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry2022

    • Author(s)
      Toganoh Motoki、Furuta Hiroyuki
    • Journal Title

      Chemical Reviews

      Volume: 122 Issue: 9 Pages: 8313-8437

    • DOI

      10.1021/acs.chemrev.1c00065

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective hetero-bis-metalation of a cisoid isomer of doubly N-confused dioxohexaphyrin2022

    • Author(s)
      Shimomura Keito、Nakamura Yuma、Kai Hiroto、Saito Kyosuke、Furukawa Ko、Mori Shigeki、Ishida Masatoshi、Furuta Hiroyuki
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 26 Issue: 12 Pages: 807-814

    • DOI

      10.1142/s1088424622500456

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Computational Study on the Mechanism of Catalytic Cyclopropanation Reaction with Cobalt N-Confused Porphyrin: The Effects of Inner Carbon and Intramolecular Axial Ligand2022

    • Author(s)
      Iwanaga Osamu、Miyanishi Mayuko、Tachibana Toshihiro、Miyazaki Takaaki、Shiota Yoshihito、Yoshizawa Kazunari、Furuta Hiroyuki
    • Journal Title

      Molecules

      Volume: 27 Issue: 21 Pages: 7266-7266

    • DOI

      10.3390/molecules27217266

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Metal complexes of 5,10,15-tris(pentafluorophenyl)-20-pyrrolyl N-confused porphyrin and its meso-pyrrolyl-bridged dimers: Synthesis and optical properties2021

    • Author(s)
      Yamasumi Kazuhisa、Mori Shigeki、Tanaka Takayuki、Ishida Masatoshi、Furuta Hiroyuki
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 25 Issue: 05n06 Pages: 447-455

    • DOI

      10.1142/s1088424621500255

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Solvent-Controlled Self-Assembled Oligopyrrolic Receptor2021

    • Author(s)
      Wang Fei、Liang Kejiang、Larsen Mads Christian、Bahring Steffen、Ishida Masatoshi、Furuta Hiroyuki、Jana Atanu
    • Journal Title

      Molecules

      Volume: 26 Issue: 6 Pages: 1771-1771

    • DOI

      10.3390/molecules26061771

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Iridium Complex of N‐Fused Bilatrienone: Oxidative Cleavage of N‐Fused Porphyrin Induced by Iridium‐Cyclooctadiene Complexation2021

    • Author(s)
      Abraham Jibin Alex、Mori Shigeki、Ishida Masatoshi、Furuta Hiroyuki
    • Journal Title

      Chemistry A European Journal

      Volume: 27 Issue: 32 Pages: 8268-8272

    • DOI

      10.1002/chem.202100789

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Heptacene and Its Hole‐Transfer Property of Stable Thin Films2021

    • Author(s)
      Miyazaki Takaaki、Watanabe Motonori、Matsushima Toshinori、Chien Ching-Ting、Adachi Chihaya、Sun Shih-Sheng、Furuta Hiroyuki、Chow Tahsin J.
    • Journal Title

      Chemistry - A European Journal

      Volume: - Issue: 41 Pages: 10677-10684

    • DOI

      10.1002/chem.202100936

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Janus Pyrrolopyrrole Aza‐dipyrrin: Hydrogen‐Bonded Assemblies and Slow Magnetic Relaxation of the Cobalt(II) Complex in the Solid State2021

    • Author(s)
      Ishizaki Toshiharu、Karasaki Hideaki、Kage Yuto、Kamioka Misaki、Wang Yitong、Mori Shigeki、Ishikawa Naoto、Fukuda Takamitsu、Furuta Hiroyuki、Shimizu Soji
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Issue: 49 Pages: 12686-12692

    • DOI

      10.1002/chem.202101755

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of N-Fused Porphyrin Rhodium Complex with an Isomerized Cyclooctadiene Ligand2021

    • Author(s)
      Abraham Jibin Alex、Mori Shigeki、Ishida Masatoshi、Furuta Hiroyuki
    • Journal Title

      Chemistry Letters

      Volume: 50 Issue: 9 Pages: 1707-1709

    • DOI

      10.1246/cl.210381

    • NAID

      130008088227

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ruthenium(IV) N-confused porphyrin μ-oxo-bridged dimers: acid-responsive molecular rotors2021

    • Author(s)
      Iwanaga Osamu、Fukuyama Kazuki、Mori Shigeki、Song Jun Tae、Ishihara Tatsumi、Miyazaki Takaaki、Ishida Masatoshi、Furuta Hiroyuki
    • Journal Title

      RSC Advances

      Volume: 11 Issue: 40 Pages: 24575-24579

    • DOI

      10.1039/d1ra05063j

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] Modulation of Aromatic Circuits in the Triply Fused N-Confused Porphyrin Dimer System2022

    • Author(s)
      Furuta Hiroyuki
    • Organizer
      12th International Conference of Porphyrins and Phthalocyanines (ICPP-12)
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] N-Confused Porphyrinoids: Directional Evolution from Porphyrin Isomer to Functional NIR Dyes2022

    • Author(s)
      Furuta Hiroyuki
    • Organizer
      XX Brazilian Meeting on Inorganic Chemistry (XXBMIC)
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 「混乱から創造へ」 混乱型ポルフィリノイドの創製と展開2022

    • Author(s)
      古田弘幸
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] 三重縮環N-混乱ポルフィリン二量体の合成と物性2022

    • Author(s)
      岩永 修、石田 真敏、古田 弘幸
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] 二光子励起光音響イメージング応用を目指した近赤外吸収BODIPY誘導体の合成と光物性2022

    • Author(s)
      嶋田 隆秀、石田 真敏、古田 弘幸
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] Synthesis and Optical Properties of Donor-Acceptor-Donor Pyrrolopyrrole aza-BODIPYs2022

    • Author(s)
      Yitong Wang, Shigeki Mori, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] Synthesis of tetraaryl-substituted 5,15-dioxaporphyrin and its oxidation to the aromatic dication2022

    • Author(s)
      Jiping Hao, Shigeki Mori, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] ケイ素テトラアザポルフィリンμ-oxo二量体の合成と分光・電気化学特性2022

    • Author(s)
      井口 まり、森 重樹、古田 弘幸、清水 宗治
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] BO縮環構造を有するピロロピロールaza-BODIPYの合成とキラル光学縮環構造を有するピロロピロールaza-BODIPYの合成とキラル光学特性2022

    • Author(s)
      深水 柊兵、森 重樹、古田 弘幸、清水 宗治
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] Push-Pull 置換基を有するケイ素テトラアザポルフィリンの合成とμ-oxo 二量化2022

    • Author(s)
      金森 隆太郎、森 重樹、古田 弘幸、清水 宗治
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] Synthesis and Ring Rotation of Ruthenium μ-Oxo N-Confused Porphyrin Dimer2021

    • Author(s)
      Osamu Iwanaga, Kazuki Fukuyama, Takaaki Miyazaki, Masatoshi Ishida, Hiroyuki Furuta
    • Organizer
      第31回万有福岡シンポジウム
    • Related Report
      2021 Research-status Report
  • [Presentation] Copper 1,19-Diazadibenzonorrole: Rational Synthesis of a Porphyrin Analogue Containing N-N Direct Linkage2021

    • Author(s)
      Biju Basumatary, Masatoshi Ishida, Hiroyuki Furuta
    • Organizer
      International Conference on Porphyrins and Phthalocyanines -11
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Ring Rotation Behavior of Ruthenium N-Confused Porphyrin [mu]-Oxo Dimers2021

    • Author(s)
      Osamu Iwanaga, Kazuki Fukuyama, Takaaki Miyazaki, Masatoshi Ishida, Hiroyuki Furuta
    • Organizer
      International Conference on Porphyrins and Phthalocyanines -11
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] "Synthesis of α- and β-Alkynylated BODIPYs via Gold(I)-catalyzed Direct C-H Functionalization and Their Photophysical Properties"2021

    • Author(s)
      Takahide Shimada, Masatoshi Ishida, Hiroyuki Furuta
    • Organizer
      "International Conference on Porphyrins and Phthalocyanines -11"
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Azabora[6]helicene誘導体の合成および光学特性2021

    • Author(s)
      水口波暉, 古田弘幸, 清水宗治
    • Organizer
      第58回 化学関連支部合同九州大会
    • Related Report
      2021 Research-status Report
  • [Presentation] N-混乱金属ポルフィリン修飾KTaO3;系光触媒による完全水分解2021

    • Author(s)
      吉田直也, 石田真敏, 古田弘幸
    • Organizer
      第58回 化学関連支部合同九州大会
    • Related Report
      2021 Research-status Report
  • [Presentation] 近赤外光吸収色素の分子構造と光熱変換特性の相関関係2021

    • Author(s)
      鶴田英寿, BijuBasumatary, 石田真敏, 古田弘幸
    • Organizer
      第58回 化学関連支部合同九州大会
    • Related Report
      2021 Research-status Report
  • [Presentation] 外部配位能を有する四置換ジオキサポルフィリンの合成2021

    • Author(s)
      池本彪流, 古田弘幸, 清水宗治
    • Organizer
      第58回 化学関連支部合同九州大会
    • Related Report
      2021 Research-status Report
  • [Presentation] 二重N-混乱ジオキソヘキサフィリンを基盤とした光音響イメージング造影剤の開発2021

    • Author(s)
      甲斐浩太郎, 甲斐寛人, 石田真敏, 古田弘幸
    • Organizer
      第58回 化学関連支部合同九州大会
    • Related Report
      2021 Research-status Report
  • [Presentation] N-混乱ポルフィリンルテニウムμ-オキソ二量体の環回転制御2021

    • Author(s)
      岩永修、福山和希、宮﨑隆聡、石田真敏、古田弘幸
    • Organizer
      九州錯体化学懇談会第261回例会
    • Related Report
      2021 Research-status Report
  • [Presentation] N-混乱金属ポルフィリン修飾Pt/KTa(Zr)O3 光触媒による水分解反応2021

    • Author(s)
      吉田直也、石田真敏、古田弘幸
    • Organizer
      第33回 若手研究者のためのセミナー
    • Related Report
      2021 Research-status Report
  • [Presentation] Ring Rotation and Restriction of Ruthenium μ-Oxo N-Confused Porphyrin Dimer2021

    • Author(s)
      Osamu Iwanaga, Kazuki Fukuyama, Takaaki Miyazaki, Masatoshi Ishida, Hiroyuki Furuta
    • Organizer
      錯体化学会第71回討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] 混乱アプローチ法による新規ポルフィリノイドの創製と機能化2021

    • Author(s)
      古田弘幸
    • Organizer
      第31回基礎有機化学討論
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] ブタジイン架橋π共役 BODIPY 二量体の合成と物性2021

    • Author(s)
      佐藤優真・石田真敏・古田弘幸
    • Organizer
      第31回基礎有機化学討論
    • Related Report
      2021 Research-status Report
  • [Presentation] ケイ素テトラアザポルフィリンμ-oxo 二量体の合成と分光特性の解明2021

    • Author(s)
      井口まり・森重樹・古田弘幸・清水宗治
    • Organizer
      第31回基礎有機化学討論
    • Related Report
      2021 Research-status Report
  • [Presentation] α-アリールエチニル BODIPY 誘導体の合成と光物性2021

    • Author(s)
      佐藤優真・石田真敏・古田弘幸
    • Organizer
      2021ハロゲン利用ミニシンポジウム
    • Related Report
      2021 Research-status Report

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Published: 2021-07-13   Modified: 2025-01-30  

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