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Development of synthetic receptors for heme based on a supramolecular chemistry approach and applications toward chemical biology

Research Project

Project/Area Number 18K06551
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionNagoya City University

Principal Investigator

Yosuke Hisamatsu  名古屋市立大学, 医薬学総合研究院(薬学), 講師 (80587270)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2020: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2019: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsヘム / 蛍光 / 人工レセプター / ホスト・ゲスト化学 / 超分子化学 / ホストゲスト化学 / 超分子 / 自己集合 / プロトポルフィリンIX / 光増感剤 / 光線力学療法 / 蛍光プローブ / ピンセット分子
Outline of Final Research Achievements

Heme plays important roles in a variety of biological systems and the development of tools for the detection of heme in living cells is important for understanding of physiological roles of heme. In this research project, new tweezer-type synthetic receptors that form stable complexes with heme were developed. Moreover, the fluorescent synthetic receptor exhibits a heme-concentration dependent fluorescence response in aqueous solution at neutral pH.

Academic Significance and Societal Importance of the Research Achievements

生体分子を水中で精密に認識する人工レセプターの開発と応用は、ホスト・ゲスト化学の分野において重要な研究課題の一つである。本研究期間において、生体内で重要な役割を持つヘムに対して高い結合親和性と蛍光応答性をもつ新規人工レセプターを開発した。今後、本研究で得られた知見を活用し改善を加えることで、ヘムの研究に貢献できる実用的なツールへと発展させたい。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report

Research Products

(19 results)

All 2021 2020 2019 2018

All Journal Article (13 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 13 results,  Open Access: 5 results) Presentation (6 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results)

  • [Journal Article] Fluorescence Response and Self‐Assembly of a Tweezer‐Type Synthetic Receptor Triggered by Complexation with Heme and Its Catabolites2021

    • Author(s)
      Hisamatsu Yosuke、Otani Koki、Takase Hiroshi、Umezawa Naoki、Higuchi Tsunehiko
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Pages: 6489-6499

    • DOI

      10.1002/chem.202003872

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structure-Based Identification of Potent Lysine-Specific Demethylase 1 Inhibitor Peptides and Temporary Cyclization to Enhance Proteolytic Stability and Cell Growth-Inhibitory Activity2021

    • Author(s)
      Kitagawa Hiroki、Kikuchi Masaki、Sato Shin、Watanabe Hisami、Umezawa Naoki、Kato Maiko、Hisamatsu Yosuke、Umehara Takashi、Higuchi Tsunehiko
    • Journal Title

      Journal of Medicinal Chemistry

      Volume: 64 Pages: 3707-3719

    • DOI

      10.1021/acs.jmedchem.0c01371

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Hydrolysis of Phosphate Monoester by Supramolecular Complexes Formed by the Self-Assembly of a Hydrophobic Bis(Zn2+-cyclen) Complex, Copper, and Barbital Units That Are Functionalized with Amino Acids in a Two-Phase Solvent System2019

    • Author(s)
      Yuya Miyazawa, Akib Bin Rahaman, Yutaka Saga, Hiroki Imafuku, Yosuke Hisamatsu, Shin Aoki
    • Journal Title

      Micromachines

      Volume: 10 Pages: 452-452

    • DOI

      10.3390/mi10070452

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Methylene chain ruler for evaluating the regioselectivity of a substrate-recognising oxidation catalyst2019

    • Author(s)
      Teramae Shota、Kito Akane、Shingaki Tomoteru、Hamaguchi Yu、Yano Yuuki、Nakayama Takamori、Kobayashi Yuko、Kato Nobuki、Umezawa Naoki、Hisamatsu Yosuke、Nagano Tetsuo、Higuchi Tsunehiko
    • Journal Title

      Chemical Communications

      Volume: 55 Pages: 8378-8381

    • DOI

      10.1039/c9cc03041g

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Design, synthesis, and anticancer activity of iridium(III) complex-peptide hybrids that contain hydrophobic acyl groups at the N-terminus of the peptide units2019

    • Author(s)
      Naito Kana、Yokoi Kenta、Balachandran Chandrasekar、Hisamatsu Yosuke、Aoki Shin
    • Journal Title

      J. Inorg. Biochem.

      Volume: 199 Pages: 110785-110785

    • DOI

      10.1016/j.jinorgbio.2019.110785

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stable Iron Porphyrin Intramolecularly Coordinated by Alcoholate Anion: Synthesis and Evaluation of Axial Ligand Effect of Alcoholate on Spectroscopy and Catalytic Activity2019

    • Author(s)
      Yoshinori Shirakawa, Yuuki Yano, Yuki Niwa, Kanako Inabe, Naoki Umezawa, Nobuki Kato, Yosuke Hisamatsu and Tsunehiko Higuchi
    • Journal Title

      Inorganic Chemistry

      Volume: 58 Pages: 4268-4274

    • DOI

      10.1021/acs.inorgchem.8b03384

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore2019

    • Author(s)
      Yosuke Hisamatsu, Takehiro Fukiage, Kojiro Honma, Andrii G. Balia, Naoki Umezawa, Nobuki Kato and Tsunehiko Higuchi
    • Journal Title

      Organic Letters

      Volume: 21 Pages: 1258-1262

    • DOI

      10.1021/acs.orglett.8b03913

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Inhibition of FAD-dependent lysine-specific demethylases by chiral polyamine analogues2018

    • Author(s)
      Naoki Umezawa, Kasumi Tsuji, Shin Sato, Masaaki Kikuchi, Hisami Watanabe, Yuhei Horai, Masashi Yamaguchi, Yosuke Hisamatsu, Takeshi Umehara and Tsunehiko Higuchi
    • Journal Title

      RSC Advances

      Volume: 8 Pages: 36895-36902

    • DOI

      10.1039/c8ra07879c

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Design and Synthesis of a 4-Aminoquinoline-Based Molecular Tweezer That Recognizes Protoporphyrin IX and Iron(III) Protoporphyrin IX and Its Application as a Supramolecular Photosensitizer2018

    • Author(s)
      Yosuke Hisamatsu, Naoki Umezawa, Hirokazu Yagi, Koichi Kato and Tsunehiko Higuchi
    • Journal Title

      Chemical Science

      Volume: 9 Pages: 7455-7467

    • DOI

      10.1039/c8sc02133c

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Potent Antimalarial Activity of Two Arenes Linked with Triamine Designed To Have Multiple Interactions with Heme2018

    • Author(s)
      Yosuke Sakata, Kosuke Yabunaka, Yuko Kobayashi, Hirohisa Omiya, Naoki Umezawa, Hye- Sook Kim, Yusuke Wataya, Yoshimi Tomita, Yosuke Hisamatsu, Nobuki Kato, Hirokazu Yagi, Tadashi Satoh, Koichi Kato, Haruto Ishikawa and Tsunehiko Higuchi
    • Journal Title

      ACS Medicinal Chemistry Letters

      Volume: 9 Pages: 980-985

    • DOI

      10.1021/acsmedchemlett.8b00222

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Luminescent Iridium Complex-Peptide Hybrids (IPHs) for Therapeutics of Cancer: Design and Synthesis of IPHs for Detection of Cancer Cells and Induction of Their Necrosis-type Cell Death2018

    • Author(s)
      Abdullah-Al Masum, Yosuke Hisamatsu, Kenta Yokoi, and Shin Aoki
    • Journal Title

      Bioinorganic Chemistry and Applications

      Volume: 2018

    • DOI

      10.1155/2018/7578965

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Design and Synthesis of a Luminescent Iridium Complex-Peptide (IPH) that Detects Cancer Cells and Induces Their Apoptosis2018

    • Author(s)
      Abdullah-Al Masum, Kenta Yokoi, Yosuke Hisamatsu, Kana Naito, Babita Shashni, and Shin Aoki,
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 26 Pages: 4804-4816

    • DOI

      10.1016/j.bmc.2018.08.016

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereospecific Synthesis of Tris-heteroleptic Tris-cyclometalated Iridium(III) Complexes via Different Heteroleptic Halogen-Bridged Iridium(III) Dimers and Their Photophysical Properties2018

    • Author(s)
      Yuichi Tamura, Yosuke Hisamatsu, Ayami Kazama, Kenji Yoza, Kyouhei, Sato, Reiko Kuroda, Shin Aok
    • Journal Title

      Inorganic Chemistry

      Volume: 57 Pages: 4571-4589

    • DOI

      10.1021/acs.inorgchem.8b00323

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Design, Synthesis and Biological Applications of 4-Aminoquinoline-Based Molecular Tweezers That Recognize Protoporphyrin IX and Heme2020

    • Author(s)
      Hisamatsu Yosuke
    • Organizer
      7th International Postgraduate Conference on Pharmaceutical Sciences (iPoPS2020)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ヘム認識能を有する蛍光性分子ピンセットの設計・合成2019

    • Author(s)
      大谷紘生、久松洋介、梅澤直樹、樋口恒彦
    • Organizer
      日本ケミカルバイオロジー学会第14回年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 水中でヘムを認識する蛍光性人工レセプターの開発2019

    • Author(s)
      久松洋介、大谷紘生、梅澤直樹、樋口恒彦
    • Organizer
      第13回バイオ関連化学シンポジウム2019
    • Related Report
      2019 Research-status Report
  • [Presentation] プロトポルフィリンIXと分子ピンセットからなる超分子型光増感剤の光線力学療法への応用2019

    • Author(s)
      久松洋介、梅澤直樹、矢木宏和、加藤晃一、樋口恒彦
    • Organizer
      日本酸化ストレス学会東海支部 第7回学術集会
    • Related Report
      2018 Research-status Report
  • [Presentation] 光線力学療法への応用を指向した超分子型光増感剤の開発2018

    • Author(s)
      久松洋介、大谷紘生、梅澤直樹、矢木宏和、加藤晃一、樋口恒彦
    • Organizer
      第12回バイオ関連化学シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] プロトポルフィリンIX及びその鉄(III)錯体を認識する分子ピンセットの設計・合成と超分子型光増感剤への応用2018

    • Author(s)
      久松洋介、大谷紘生、梅澤直樹、矢木宏和、加藤晃一、樋口恒彦
    • Organizer
      第16回ホスト-ゲスト・超分子化学シンポジウム
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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