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Study on the key reaction mechanisms and chemical factors for high-performance luminescence in bioluminescence systems

Research Project

Project/Area Number 18K05075
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionThe University of Electro-Communications

Principal Investigator

Hirano Takashi  電気通信大学, 大学院情報理工学研究科, 教授 (20238380)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2018: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywords生物発光 / ホタル / ウミホタル / ルシフェリン / ルシフェラーゼ / 反応機構 / 酸素化 / 化学励起 / オキシルシフェリン / 酵素環境場
Outline of Final Research Achievements

Luciferin-luciferase (L-L) reactions of firefly and ostracod bioluminescence are widely applied for biological analysis and imaging. To support the development of their applications, we need to understand the mechanisms of the L-L reactions made up by several elemental processes. For the purpose, we carried out mechanistic studies on the three important processes, oxygenation, chemiexcitation, and emission from the excited oxyluciferins in the L-L reactions. The results provide information on the molecular mechanisms to design luciferin derivatives with high-performance luminescence property.

Academic Significance and Societal Importance of the Research Achievements

生物発光は化学反応により光子を生み出す特徴を持ち、生命科学分野の発光分析やイメージング技術を支える。生物発光の分析利用を発展させるには、基盤となる反応機構の理解が不可欠であり、本研究で得られた素反応過程の分子機構に関する知見は、高性能な生物発光を模倣した発光基質の分子設計指針を提供するため学術的意義が大きい。さらに、生物発光の分析利用法の高性能化に寄与することで、医療を含めた生命科学分野の発展にも貢献する。

Report

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

    (47 results)

All 2021 2020 2019 2018 Other

All Int'l Joint Research (3 results) Journal Article (11 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 11 results,  Open Access: 5 results) Presentation (30 results) (of which Int'l Joint Research: 6 results) Book (2 results) Remarks (1 results)

  • [Int'l Joint Research] Federal University of Sao Carlos(ブラジル)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] Federal University of Sao Carlos(ブラジル)

    • Related Report
      2019 Research-status Report
  • [Int'l Joint Research] Federal University of Sao Carlos(ブラジル)

    • Related Report
      2018 Research-status Report
  • [Journal Article] Color-tunable bioluminescence imaging portfolio for cell imaging2021

    • Author(s)
      Tamaki Shota、Kitada Nobuo、Kiyama Masahiro、Fujii Rika、Hirano Takashi、Kim Sung Bae、Maki Shojiro
    • Journal Title

      Scientific Reports

      Volume: 11 Issue: 1 Pages: 2219-2219

    • DOI

      10.1038/s41598-021-81430-1

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of polyenylpyrrole derivatives with selective growth inhibitory activity against T-cell acute lymphoblastic leukemia cells2021

    • Author(s)
      Yoshida Chihiro、Higashi Tomoya、Hachiro Yoshifumi、Fujita Yuki、Yagi Takuya、Takechi Azusa、Nakata Chihiro、Miyashita Kazuya、Kitada Nobuo、Saito Ryohei、Obata Rika、Hirano Takashi、Hara Takahiko、Maki Shojiro A.
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 37 Pages: 127837-127837

    • DOI

      10.1016/j.bmcl.2021.127837

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of near‐infrared firefly luciferin analogue reacted with wild‐type and mutant luciferases2020

    • Author(s)
      Kitada Nobuo、Saito Ryohei、Obata Rika、Iwano Satoshi、Karube Kazuma、Miyawaki Atsushi、Hirano Takashi、Maki Shojiro A.
    • Journal Title

      Chirality

      Volume: 32 Issue: 7 Pages: 922-931

    • DOI

      10.1002/chir.23236

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Very Bright Far-Red Bioluminescence Emitting Combination Based on Engineered Railroad Worm Luciferase and 6′-Amino-Analogs for Bioimaging Purposes2020

    • Author(s)
      Viviani Vadim R.、Bevilaqua Vanessa R.、de Souza Daniel R.、Pelentir Gabriel F.、Kakiuchi Michio、Hirano Takashi
    • Journal Title

      International Journal of Molecular Sciences

      Volume: 22 Issue: 1 Pages: 303-303

    • DOI

      10.3390/ijms22010303

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Isomeric difference in the crystalline-state chemiluminescence property of an adamantylideneadamantane 1,2-dioxetane with a phthalimide chromophore2020

    • Author(s)
      Matsuhashi Chihiro、Ueno Takuya、Uekusa Hidehiro、Sato-Tomita Ayana、Ichiyanagi Kouhei、Maki Shojiro、Hirano Takashi
    • Journal Title

      Chemical Communications

      Volume: 56 Issue: 23 Pages: 3369-3372

    • DOI

      10.1039/c9cc10012a

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Bright near-infrared chemiluminescent dyes: Phthalhydrazides conjugated with fluorescent BODIPYs2020

    • Author(s)
      Li Guanglei、Hirano Takashi、Yamada Koji
    • Journal Title

      Dyes and Pigments

      Volume: 178 Pages: 108339-108339

    • DOI

      10.1016/j.dyepig.2020.108339

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Phrixotrix luciferase and 6′-aminoluciferins reveal a larger luciferin phenolate binding site and provide novel far-red combinations for bioimaging purposes2019

    • Author(s)
      Bevilaqua V. R.、Matsuhashi T.、Oliveira G.、Oliveira P. S. L.、Hirano T.、Viviani V. R.
    • Journal Title

      Scientific Reports

      Volume: 9 Issue: 1

    • DOI

      10.1038/s41598-019-44534-3

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Halogen-substituent effect on the spectroscopic properties of 2-phenyl-6-dimethylaminobenzothiazoles2019

    • Author(s)
      Misawa Rena、Matsuhashi Chihiro、Yamaji Minoru、Mutai Toshiki、Yoshikawa Isao、Houjou Hirohiko、Noguchi Keiichi、Maki Shojiro、Hirano Takashi
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 26 Pages: 1702-1705

    • DOI

      10.1016/j.tetlet.2019.05.052

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and luminescence properties of near-infrared N-heterocyclic luciferin analogues for in vivo optical imaging2019

    • Author(s)
      Ryohei Saito, Takahiro Kuchimaru, Shoko Higashi, Shijia W. Lu, Masahiro Kiyama, Satoshi Iwano, Rika Obata, Takashi Hirano, Shinae Kizaka-Kondoh, Shojiro A. Maki
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 92 Issue: 3 Pages: 608-618

    • DOI

      10.1246/bcsj.20180350

    • NAID

      130007612635

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Spectroscopic properties of push-pull 2-(4-carboxyphenyl-6-dimethylaminobenzothiazole derivatives in solution and the solid state2019

    • Author(s)
      Takahashi, Yusuke; Uehara, Takuya; Matsuhashi, Chihiro; Yamaji, Minoru; Mutai, Toshiki; Yoshikawa, Isao; Houjou, Hirohiko; Kitagawa, Kota; Suenobu, Tomoyoshi; Maki, Shojiro; Hirano, Takashi
    • Journal Title

      Journal of Photochemistry and Photobiology, A: Chemistry

      Volume: 376 Pages: 324-332

    • DOI

      10.1016/j.jphotochem.2019.03.021

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] The proton and metal binding sites responsible for the pH-dependent green-red bioluminescence color tuning in firefly luciferases2018

    • Author(s)
      Vadim R. Viviani, Gabriele V. M. Gabriel, Vanessa R. Bevilaqua, A. F. Simoes, T. Hirano, P. S. Lopes-de-Oliveira
    • Journal Title

      Sci. Rep.

      Volume: 8 Issue: 1 Pages: 17594-17594

    • DOI

      10.1038/s41598-018-33252-x

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] アミノルシフェリンアナログのホタル生物発光特性2021

    • Author(s)
      鈴木雄大, 牧昌次郎,平野 誉
    • Organizer
      日本化学会第101春季年会(web開催)
    • Related Report
      2020 Annual Research Report
  • [Presentation] マルチカラー発光を示す海洋生物由来発光システムの開発2021

    • Author(s)
      北田昇雄,玉城翔太,木山正啓,金 誠培,平野 誉,牧昌次郎
    • Organizer
      日本化学会第101春季年会(web開催)
    • Related Report
      2020 Annual Research Report
  • [Presentation] 置換基導入型アミノルシフェリンのホタル生物発光特性2020

    • Author(s)
      鈴木雄大, 牧昌次郎,平野 誉
    • Organizer
      2020年web光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Modulation of firefly bioluminescence with aminoluciferin analogues having an additional substituent2020

    • Author(s)
      Yudai Suzuki, Shojiro Maki, Takashi Hirano
    • Organizer
      Virtual Irago Conference 2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] 長波長発光を示すセレンテラジン類縁体の開発2020

    • Author(s)
      玉城翔太,木山正啓,北田昇雄,盛満 玲,金 誠培,平野 誉,牧昌次郎
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 近赤外発光を示すホタルルシフェリンアナログの合成2020

    • Author(s)
      神谷弦汰,北田昇雄,齊藤亮平,岩野 智,宮脇敦史,平野 誉,牧昌次郎
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] ルシフェリン構造改変によるホタル生物発光機構の解明2020

    • Author(s)
      伊藤真一,牧昌次郎,平野 誉
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 置換基導入型アミノルシフェリンによるホタル生物発光特性制御2020

    • Author(s)
      鈴木雄大,牧昌次郎,平野 誉
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] ルシフェリン構造改変に基づくホタル生物発光の反応機構解明2019

    • Author(s)
      伊藤真一,牧昌次郎,平野 誉
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] ホタル発光系の波長制御機構研究:エノール型発光体の蛍光特性評価2019

    • Author(s)
      平賀詩織,山路 稔,牧昌次郎,平野 誉
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 長波長発光を示すセレンテラジン類縁体2019

    • Author(s)
      玉城翔太,木山正啓,盛満 玲,平野 誉,牧昌次郎
    • Organizer
      生物発光化学発光研究会第35回学術講演会
    • Related Report
      2019 Research-status Report
  • [Presentation] ホタル生物発光系の波長制御機構の解明:エノール型オキシルシフェリンの蛍光特性評価2019

    • Author(s)
      平賀詩織,山路 稔,牧昌次郎,平野 誉
    • Organizer
      生物発光化学発光研究会第35回学術講演会
    • Related Report
      2019 Research-status Report
  • [Presentation] ホタル生物発光における酸素化のモデル反応による反応機構解明2019

    • Author(s)
      伊藤真一,牧昌次郎,平野 誉
    • Organizer
      生物発光化学発光研究会第35回学術講演会
    • Related Report
      2019 Research-status Report
  • [Presentation] Color Modulation in the Firefly Bioluminescence: Mechanism Elucidation Based on the Fluorescence Property of the Enol-form of Oxyluciferins2019

    • Author(s)
      Shiori Hiraga, Michio Kakiuchi, Shojiro Maki, Takashi Hirano
    • Organizer
      The Irago Conference 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Oxygenation Model Reactions of the Firefly Bioluminescence2019

    • Author(s)
      Shinichi Ito, Shojiro Maki, Takashi Hirano
    • Organizer
      The Irago Conference 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] ホタル生物発光の酸素化反応機構2019

    • Author(s)
      伊藤真一,牧昌次郎,平野 誉
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ホタル生物発光系の波長制御機構の解明:エノール型オキシルシフェリンの蛍光特性の評価2019

    • Author(s)
      平賀詩織,山路 稔,牧昌次郎,平野 誉
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ホタル型マルチカラー蛍光色素構造を用いたラベル化試薬の合成2019

    • Author(s)
      三澤玲菜,山路 稔,牧昌次郎,平野 誉
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] in vivo 光イメージングに適した新規ルシフェリンアナログの開発2019

    • Author(s)
      齊藤亮平,北田昇雄,平野 誉,牧昌次郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ホタルデヒドロルシフェリン誘導体を用いた酵素活性部位の分子環境の評価2018

    • Author(s)
      有年聖良,山路 稔,牧昌次郎,平野 誉
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ホタル型蛍光色素骨格を用いたラベル化試薬開発2018

    • Author(s)
      三澤玲菜,山路 稔,牧昌次郎,平野 誉
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ホタル発光系の波長制御機構研究:オキシ体の分子構造と蛍光特性の評価2018

    • Author(s)
      平賀詩織,垣内美知雄,牧昌次郎,平野 誉
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ホタル生物発光における酸素化過程の分子機構解明2018

    • Author(s)
      伊藤真一,牧昌次郎,平野 誉
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 置換基効果によるホタル発光系の発光特性制御2018

    • Author(s)
      垣内美知雄,伊東綜一郎,後藤史也,松橋拓人,木山正啓,山路 稔,牧昌次郎,平野 誉
    • Organizer
      生物発光化学発光研究会第34回学術講演会
    • Related Report
      2018 Research-status Report
  • [Presentation] 水溶性向上型近赤外ルシフェリンアナログの開発2018

    • Author(s)
      齊藤亮平,北田昇雄,木山正啓,東 翔子,Lu Shijia W.,小畠りか,平野 誉,牧昌次郎
    • Organizer
      生物発光化学発光研究会第34回学術講演会
    • Related Report
      2018 Research-status Report
  • [Presentation] Luminol-based chemiluminescent boron dipyrromethene dyes emitting in near-infrared (NIR) region2018

    • Author(s)
      李 光磊,福世泰秀,平野 誉,山田幸司
    • Organizer
      生物発光化学発光研究会第34回学術講演会
    • Related Report
      2018 Research-status Report
  • [Presentation] The electron transfer oxygenation mechanism in firefly bioluminescence2018

    • Author(s)
      Shinichi Ito, Shojiro Maki, Takashi Hirano
    • Organizer
      The Irago Conference 2018
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Color modulation mechanism of the firefly bioluminescence: a structure-fluorescence property relationship of oxyluciferins2018

    • Author(s)
      Shiori Hiraga, Michio Kakiuchi, Shojiro Maki, Takashi Hirano
    • Organizer
      The Irago Conference 2018
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of a thiol labeling reagent with a firefly-type fluorophore structure2018

    • Author(s)
      Rena Misawa, Minoru Yamaji, Shojiro Maki, Takashi Hirano
    • Organizer
      The Irago Conference 2018
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Characterization of the firefly luciferase property with dehydroluciferin derivatives2018

    • Author(s)
      Seira Aritoshi, Minoru Yamaji, Shojiro Maki, Takashi Hirano
    • Organizer
      The Irago Conference 2018
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Book] CSJ Current Review 36, 「生体分子反応を制御する-化学的手法による機構と反応場の解明」“10章 生物発光反応の制御方法” 担当2020

    • Author(s)
      日本化学会編(著者の一人として参加)
    • Total Pages
      212
    • Publisher
      化学同人
    • ISBN
      9784759813968
    • Related Report
      2019 Research-status Report
  • [Book] 光化学フロンティア-未来材料を生む有機光化学の基礎2018

    • Author(s)
      平野 誉(「第15章光生命科学」担当)(編集:水野一彦,宮坂 博,池田 浩)
    • Total Pages
      436
    • Publisher
      化学同人
    • ISBN
      9784759814194
    • Related Report
      2018 Research-status Report
  • [Remarks] 電気通信大学 研究者情報総覧

    • URL

      http://kjk.office.uec.ac.jp/Profiles/4/0000395/profile.html

    • Related Report
      2020 Annual Research Report

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

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