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Ligand-Directed Selective Protein Modification Based on Local Single- Electron-Transfer Catalysis

Research Project

Project/Area Number 25810104
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Bio-related chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

SATO Shinichi  東京工業大学, 資源化学研究所, 助教 (20633134)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2014: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsタンパク質化学修飾 / ケミカルラベリング / チロシン残基修飾 / タンパク質機能化 / 標的タンパク質 / 光触媒 / Ru(bpy)3 / 一電子移動反応 / タンパク質ラベル化 / 一電子酸化 / 選択的ラベル化 / チロシン修飾 / ラジカル反応 / タンパク質分子修飾
Outline of Final Research Achievements

The chemical modification of proteins with synthetic probes is an important technique in chemical biology, protein-based therapy, and material science. It is an essential tool for the development of antibody-drug conjugates and protein-based drug delivery agents. Furthermore, The target-protein-selective chemical modification with small-molecule probes has received much interest as a powerful method for the study of individual proteins in their native environments.
We developed tyrosine-selective bioconjugation reaction using single-electron-transfer (SET) reaction. We found tyrosine modification reaction using a Ru(bpy)3 photocatalyst as a SET catalyst. N’-acetyl-N,N-dimethyl-1,4-phenylenediamine was found to be a suitable tyrosine modifier under the reaction condition with Ru(bpy)3 and visible light irradiation even in mild pH conditions (pH 6.0-7.4).
The target-selective protein modification was achieved using a ligand-conjugated Ru(bpy)3.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (33 results)

All 2015 2014 2013 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 3 results) Presentation (23 results) (of which Invited: 1 results) Remarks (2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Regulation of Target Protein Knockdown and Labeling Using Ligand-Directed Ru(bpy)3 Photocatalyst2015

    • Author(s)
      Sato S., Morita M., Nakamura H.
    • Journal Title

      Bioconjugate Chem

      Volume: 26 Issue: 2 Pages: 250-256

    • DOI

      10.1021/bc500518t

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Diaryl-substituted ortho-carboranes as a new class of hypoxia inducible factor-1α inhibitors2014

    • Author(s)
      H. Nakamura, L. Tazaki, D. Kanoh, S. Sato, H. H. Ban
    • Journal Title

      J. Chem. Soc., Dalton Trans

      Volume: 43 Issue: 13 Pages: 4941-4944

    • DOI

      10.1039/c3dt52828f

    • Related Report
      2014 Annual Research Report 2013 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of protoporphyrin lipids and biological evaluation of micelles and liposomes2014

    • Author(s)
      S. Tachikawa, M. E. El-Zaria, R. Inomata, S. Sato, H. Nakamura
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 22 Issue: 17 Pages: 4745-4751

    • DOI

      10.1016/j.bmc.2014.07.003

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Design of Photoaffinity Probe Molecules for Identification and Modification of Target Proteins2014

    • Author(s)
      Nakamura H., Ban H. S., Shimizu K.., Minegishi H., Sato S.
    • Journal Title

      Journal of Photopolymer Science and Technology

      Volume: 27 Issue: 4 Pages: 453-458

    • DOI

      10.2494/photopolymer.27.453

    • NAID

      130004687610

    • ISSN
      0914-9244, 1349-6336
    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Hypoxia-Inducible Factor (HIF)-1α Inhibitors: Effect of ortho-Carborane Substituents on HIF Transcriptional -Activity under Hypoxia 23, 1455-1461 (2013).2013

    • Author(s)
      H. Nakamura, Y. Yasui, M. Maruyama, H. Minegishi, H. S. Ban, S. Sato,
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 23 Issue: 3 Pages: 1455-1461

    • DOI

      10.1016/j.bmcl.2012.11.081

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ligand-directed Selective Protein Modification Based on Local Single Electron Transfer Catalysis2013

    • Author(s)
      S. Sato and H. Nakamura
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52 Issue: 33 Pages: 8681-8684

    • DOI

      10.1002/anie.201303831

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chemically Programmed Antibodies As HIV-1 Attachment Inhibitors.2013

    • Author(s)
      S. Sato, T. Inokuma, N. Otsubo, D. R. Burton, C. F. Barbas III
    • Journal Title

      ACS Med. Chem. Lett.

      Volume: 4 Issue: 5 Pages: 460-465

    • DOI

      10.1021/ml400097z

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] ルミノール誘導体を用いた鉄触媒存在下でのTyr 残基特異的タ ンパク質ラベル化反応2015

    • Author(s)
      中村公亮、佐藤伸一、中村 浩之
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 中性子捕捉療法のための血清アルブミンを用いた新しいホウ素 送達法の開発2015

    • Author(s)
      菊地俊介、加納大輔、佐藤伸一、中 村浩之
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] リガンド連結型Ru光触媒を用いたタンパク質ノックダウンとラベル化の制御2015

    • Author(s)
      佐藤伸一、森田耕平、中村浩之
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 標的タンパク質のラベル化を指向した一電子酸化的チロシン残基修飾反応の開発2014

    • Author(s)
      佐藤伸一、中村浩之
    • Organizer
      第68回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] Target-selective Protein Modification Based on Local Environmental Single Electron Transfer Catalysis2014

    • Author(s)
      S. Sato, H. Nakamaura
    • Organizer
      18th Malaysian International Chemical Congress
    • Place of Presentation
      Kuala Lumpur, Malaysia
    • Year and Date
      2014-11-03 – 2014-11-05
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 一電子酸化触媒を用いたタンパク質のチロシン残基修飾法開発と応用2014

    • Author(s)
      佐藤伸一
    • Organizer
      第1回 資源研フォーラム
    • Place of Presentation
      東京
    • Year and Date
      2014-10-21 – 2014-10-22
    • Related Report
      2014 Annual Research Report
  • [Presentation] Diaryl-substituted carboranes as inhibitors of hypoxia inducible factor-1 transcriptional activity2014

    • Author(s)
      H. Nakamura, L. Tazaki, D. Kanoh, S. Sato, H. S. Ban,
    • Organizer
      XV Internationl Meeting of Boron Chemistry, Key Note Lecture
    • Place of Presentation
      Prague, Zech
    • Year and Date
      2014-08-24 – 2014-08-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Target-selective Protein Modification Using Ligand-conjugated Ru(bpy)3 Catalyst2014

    • Author(s)
      H.Nakamaura, S. Sato
    • Organizer
      XXVI International Congress of Organometallic Chemistry
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] がん光線力学的治療のためのポルフィリン脂質の開発とナノキャリアへの応用2014

    • Author(s)
      立川将士、佐藤伸一、間久直、粟津邦男、金田安史、中村浩之
    • Organizer
      創薬懇親会2014
    • Place of Presentation
      岐阜
    • Year and Date
      2014-07-10 – 2014-07-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] カルボラン骨格を有する新規Hsp60阻害剤の開発2014

    • Author(s)
      東礎代子、李廣哲、佐藤伸一、中村浩之
    • Organizer
      創薬懇親会2014
    • Place of Presentation
      岐阜
    • Year and Date
      2014-07-10 – 2014-07-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] Design of Photoaffinity Proble Molecules for Identification and Modification of Target Proteins2014

    • Author(s)
      H. Nakamura, H. S. Ban, K. Shimizu, H. Minegishi, S. Sato
    • Organizer
      The 31st International Conference of Photopolymer Science and Technology Materials & Processes for Advanced Microlithography, Nanotechnology and Phototechnology
    • Place of Presentation
      千葉
    • Year and Date
      2014-07-08 – 2014-07-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] 生体高分子をキャリアとしたホウ素デリバリーシステム:マレイミドドデカボレート(MID)の開発と生物活性評価2014

    • Author(s)
      加納大輔、立川将士、佐藤伸一、近藤夏子、鈴木実、桜井良憲、小野公二、中村浩之
    • Organizer
      第11回日本中性子捕捉療法学会学術大会
    • Place of Presentation
      大阪
    • Year and Date
      2014-07-05 – 2014-07-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] Development of Albumin-bound closo-Dodecaborate and its Promising Boron Delivery Efficacy to Tumor2014

    • Author(s)
      Daisuke Kanoh, Shoji Tachikawa, Shinich Sato, Hiroyuki Nakamura
    • Organizer
      16th International Congress on Neutron Capture Therapy
    • Place of Presentation
      Finland
    • Year and Date
      2014-06-14 – 2014-06-19
    • Related Report
      2014 Annual Research Report
  • [Presentation] リガンド連結型Ru(bpy)3触媒を用いた標的選択的タンパク質光分解とラベル化反応の制御2014

    • Author(s)
      佐藤伸一、森田耕平、中村浩之
    • Organizer
      日本ケミカルバイオロジー学会 第9回年会
    • Place of Presentation
      大阪
    • Year and Date
      2014-06-11 – 2014-06-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] Luminol誘導体を用いた鉄触媒存在下でのTyr残基高選択的ラベル化反応2014

    • Author(s)
      中村公亮、佐藤伸一、中村浩之
    • Organizer
      日本ケミカルバイオロジー学会 第9回年会
    • Place of Presentation
      大阪
    • Year and Date
      2014-06-11 – 2014-06-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] 光触媒を利用した生体内標的タンパク質ラベル化法の開発2014

    • Author(s)
      佐藤伸一、中村浩之
    • Organizer
      新学術領域研究「天然物ケミカルバイオロジー~分子標的と活性制御~」 第6回公開シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2014-05-28 – 2014-05-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] カルボラン骨格を基盤とした新規Hsp60阻害剤の開発2014

    • Author(s)
      東礎代子、佐藤伸一、安井友香、丸山美菜子、潘鉉承、中村浩之
    • Organizer
      文科省新学術領域研究・がん支援「化学療法基盤支援活動」第3回シンポジウム
    • Place of Presentation
      沖縄
    • Year and Date
      2014-05-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] インデノピラゾール化合物による低酸素応答および細胞増殖に対する効果2014

    • Author(s)
      峯岸秀充、深代真司、佐藤伸一、中村浩之
    • Organizer
      文科省新学術領域研究・がん支援「化学療法基盤支援活動」第3回シンポジウム
    • Place of Presentation
      沖縄
    • Year and Date
      2014-05-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] 一電子酸化反応に基づくチロシン残基修飾法の開発と標的タンパク質選択的ラベル化法への応用2014

    • Author(s)
      佐藤 伸一、中村 浩之
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] 標的指向性Ru(bpy)3錯体をもちいた局所環境での一電子酸化反応の制御と標的タンパク質選択ラベル化法への応用2013

    • Author(s)
      佐藤 伸一、中村 浩之
    • Organizer
      第60回有機金属討論会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] Target-selective Protein Labeling Based on Local Single Electron Transfer Catalysis2013

    • Author(s)
      Shinichi Sato, Hiroyuki Nakamura
    • Organizer
      The 2nd International Symposium on Chemical Biology of Natural Products: Target ID and Regulation of Bioactivity
    • Place of Presentation
      横浜
    • Related Report
      2013 Research-status Report
  • [Presentation] Ligand-directed Selective Protein Modification Based on Local Environmental Single Electron Transfer Catalysis2013

    • Author(s)
      Shinichi Sato, Hiroyuki Nakamura
    • Organizer
      International Chemical Biology Society 2nd Annual Conference ICBS2013
    • Place of Presentation
      京都
    • Related Report
      2013 Research-status Report
  • [Presentation] 局所環境での一電子酸化反応を利用した標的タンパク質選択的ラベル化法の開発2013

    • Author(s)
      佐藤 伸一、中村 浩之
    • Organizer
      日本ケミカルバイオロジー学会第8回年会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Remarks] 東京工業大学 資源化学研究所合成化学部門 中村・布施研究室ホームページ

    • URL

      http://www.syn.res.titech.ac.jp/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 東京工業大学資源化学研究所 中村・谷口研HP

    • URL

      http://www.syn.res.titech.ac.jp/research.htm

    • Related Report
      2013 Research-status Report
  • [Patent(Industrial Property Rights)] チロシンの修飾方法2014

    • Inventor(s)
      佐藤伸一、中村浩之
    • Industrial Property Rights Holder
      佐藤伸一、中村浩之
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-246487
    • Filing Date
      2014-12-05
    • Related Report
      2014 Annual Research Report

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Published: 2014-07-25   Modified: 2019-07-29  

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