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Development of copper(I) fluorescent sensors based on photoinduced electron transfer mechanism and their application to optical imaging of cells

Research Project

Project/Area Number 21750168
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemistry related to living body
Research InstitutionKyoto University

Principal Investigator

TAKI Masayasu  Kyoto University, 地球環境学堂, 助教 (70378850)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2009: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Keywords生物無機化学 / バイオセンサー / 銅一価蛍光プローブ / 蛍光イメージング / 還元型フルオレセイン / ミトコンドリア局在型 / ローダミン誘導体 / チオエーテル配位子 / 光誘起電子移動 / 銅一価イオン / 蛍光プローブ / 結晶構造 / 酸化還元電位
Research Abstract

We have developed copper(I)-selective fluorescent probes as a chemical tool for monitoring behavior of copper ions in living cells. We initially synthesized various tioether-containing ligands and prepared the corresponding copper(I) complexes. Spectroscopic measurements and X-ray crystal structure analysis of these copper(I) complexes indicate that the linker chain length of the thioether ligand strongly affect the affinity toward copper(I) ion, binding fashion, and redox potential of copper. We next developed novel copper(I) fluorescent probes based on the oxidative cleavage mechanism. These probes contain a reduced form of fluorescein and TPA tetradentate ligand, those are linked through a benzyl ether group. We found that strong fluorescence is observed when copper(I) is added to the probe solution containing sub mM of gluthatione in water. The same reaction undergoes even in cells. Therefore, this will be useful chemical tool to probe intracellular copper(I) ion behavior.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (39 results)

All 2011 2010 2009 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (29 results) Remarks (1 results)

  • [Journal Article] Electron microscopic visualization of the filament binding mode of actin binding proteins.2011

    • Author(s)
      T.Ito, T.Hirayama, M.Taki, S.Iyoshi, S.Dai, S.Takeda, C.Kimura-Sakiyama, T.Oda, Y.Yamamoto, Y.Maeda, A.Narita
    • Journal Title

      Journal of Molecular Biology 408

      Pages: 26-39

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Human spire interacts with the barbed end of the actin filament.2011

    • Author(s)
      T.Ito, A.Narita, T.Hirayama, M.Taki, S.Iyoshi, Y.Yamamoto, Y.Maeda, T.Oda
    • Journal Title

      Journal of Molecular Biology 408

      Pages: 18-25

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Fluorescent Probe for Polyhistidine Tag Using Macrocyclic Nickel(II) Complex and Fluorescein Conjugate.2011

    • Author(s)
      M.Taki, F.Asahi, T.Hirayama, Y.Yamamoto
    • Journal Title

      Bulletin of the Chemical Society of Japan 84

      Pages: 386-394

    • NAID

      10028046840

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Human spire interacts with the barbed end of the actin filament.2011

    • Author(s)
      T.Ito, A.Narita, T.Hirayama, M.Taki, S.Iyoshi, Y.Yamamoto, Y.Maeda, T.Oda
    • Journal Title

      Journal of Molecular Biology

      Volume: 408 Pages: 18-25

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electron Microscopic Visualization of the Filament Binding Mode of Actin-Binding Proteins2011

    • Author(s)
      T.Ito, T.Hirayama, M.Taki, S.Iyoshi, S.Dai, S.Takeda, C.Kimura-Sakiyama, T.Oda, Y.Yamamoto, Y.Maeda, A.Narita
    • Journal Title

      Journal of Molecular Biology

      Volume: 408 Pages: 26-39

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Highly Sensitive Fluorescent Probes for Detection of Intracellular Copper(I) in Living Systems.2010

    • Author(s)
      M.Taki, S.Iyoshi, A.Ojida, I.Hamachi, Y.Yamamoto
    • Journal Title

      Journal of the American Chemical Society 132

      Pages: 5938-5939

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Development of Highly Sensitive Fluorescent Probes for Detection of Intracellular Copper(I) in Living Systems.2010

    • Author(s)
      M.Taki, S.Iyoshi, A.Ojida, I.Hamachi, Y.Yamamoto
    • Journal Title

      Journal of the American Chemical Society

      Volume: 132 Pages: 5938-5939

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective labeling of tag-fused protein by tryptophan-sensitized luminescence of a terbium complex.2009

    • Author(s)
      T.Hirayama, M.Taki, A.Kodan, H.Kato, Y.Yamamoto
    • Journal Title

      Chemical Communications

      Pages: 3196-3198

    • Related Report
      2010 Final Research Report 2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of ratiometric fluorescent probe for zinc ion based on indole fluorophore.2009

    • Author(s)
      M.Taki, Y.Watanabe, Y.Yamamoto
    • Journal Title

      Tetrahedron Letters 50

      Pages: 1345-1347

    • Related Report
      2010 Final Research Report 2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] TPA型四座配位子を用いた銅-活性酸素錯体によるC-H結合活性化機構の解明2011

    • Author(s)
      水川友章・酒井尚子・多喜正泰・山本行男
    • Organizer
      日本化学会第91春季年会,日本化学会第91春季年会(2011)講演予稿集
    • Year and Date
      2011-03-11
    • Related Report
      2010 Final Research Report
  • [Presentation] TPA型四座配位子を用いた銅-活性酸素錯体によるC-H結合活性化機構の解明2011

    • Author(s)
      水川友章・酒井尚子・多喜正泰・山本行男
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (日本化学会第91春季年会(2011)講演予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] CS124骨格を有する時間分解型亜鉛蛍光プローブの開発2011

    • Author(s)
      山元雅信・伊吉祥平・多喜正泰・山本行男
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (日本化学会第91春季年会(2011)講演予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] 還元型フルオレセイン骨格を有する新規レシオ型銅一価蛍光プローブの開発2011

    • Author(s)
      伊吉祥平・多喜正泰・山本行男
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (日本化学会第91春季年会(2011)講演予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] 新規Ni-NTAオリゴマーの開発とポリヒスチジンとの結合挙動2011

    • Author(s)
      赤岡一志・多喜正泰・山本行男
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (日本化学会第91春季年会(2011)講演予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] 細胞膜外縁部における局所的亜鉛濃度変化の検出を指向した新規蛍光プローブの開発2011

    • Author(s)
      伊吉祥平・多喜正泰・山本行男
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (日本化学会第91春季年会(2011)講演予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] チオエーテル配位子を有する銅一価錯体の構造及び物理化学的性質2011

    • Author(s)
      吉田兆志・伊吉祥平・多喜正泰・山本行男
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (日本化学会第91春季年会(2011)講演予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] 様々な配位子を有する還元型フルオレセイン誘導体の開発2011

    • Author(s)
      阿部瑞紀・多喜正泰・山本行男
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (日本化学会第91春季年会(2011)講演予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] Development of a novel copper(I) fluorescent probe utilizing copper-dioxygen activation mechanism2010

    • Author(s)
      M.Taki, S.Iyoshi, Y.Yamamoto
    • Organizer
      Pacifichem2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Mechanistic studies on the intramolecular debenzylation by copper-dioxygen complexes supported by TPA derivatives2010

    • Author(s)
      Tomoaki Mizukawa, Masayasu Taki, Naoko Sakai, Yukio Yamamoto
    • Organizer
      Pacifichem2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Structural, electrochemical, and photophysical properties of fluorescent copper probes containing multidentate thioether ligand2010

    • Author(s)
      Shohei Iyoshi, Masayasu Taki, Yukio Yamamoto
    • Organizer
      Pacifichem2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Development of Copper(I)-selective Fluorescent Probes Based on a Reduced Form of Fluorescein2010

    • Author(s)
      M.Taki, S.Iyoshi, Y.Yamamoto
    • Organizer
      60th Anniversary Conference on Coordination Chemistry in OSAKA, Osaka (大阪国際交流センター)
    • Place of Presentation
      Japan
    • Year and Date
      2010-09-28
    • Related Report
      2010 Final Research Report
  • [Presentation] Development of Copper(I)-selective Fluorescent Probes Based on a Reduced Form of Fluorescein2010

    • Author(s)
      Masayasu Taki, Shohei Iyoshi, Yukio Yamamoto
    • Organizer
      60CCCO
    • Place of Presentation
      大阪国際交流センター(大阪市)
    • Year and Date
      2010-09-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] フェノキシメチル基を有するTPA四座配位子の銅一価およひ〓二価錯体の構造と反応性2010

    • Author(s)
      水川友章・酒井尚子・多喜正泰・山本行男
    • Organizer
      第60回錯体化学討論会
    • Place of Presentation
      大阪国際交流センター(大阪市)
    • Year and Date
      2010-09-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] 局所的亜鉛濃度変化の検出を指向した新規蛍光センサーの開発2010

    • Author(s)
      伊吉祥平・多喜正泰・山本行男
    • Organizer
      生体機能関連化学若手の会 第22回サマースクール
    • Place of Presentation
      関ロッジ(三重県亀山市)
    • Year and Date
      2010-07-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] 局所的亜鉛濃度変化の検出を指向した新規蛍光センサーの開発2010

    • Author(s)
      伊吉祥平・多喜正泰・山本行男
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学(大阪府)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] 蛍光性希土類錯体を用いた亜鉛センサーペプチドの開発2010

    • Author(s)
      白川佳徳・多喜正泰・山本行男
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学(大阪府)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] フルオレセイン結合型環状配位子を用いたニッケル錯体の合成と性質2010

    • Author(s)
      旭史悦・多喜正泰・山本行男
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学(大阪府)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] 還元型フルオレセイン骨格を利用した銅一価イオン蛍光検出機構の解明2010

    • Author(s)
      水川友章・多喜正泰・山本行男
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学(大阪府)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] Design and Synthesis of Visible-Excitable Fluorescent Probe for Polyhistidine Tag Using Macrocyclic Nickel (II) Complex2010

    • Author(s)
      M.Taki, F.Asahi, Y.Yamamoto
    • Organizer
      The 5th Asian Biological Inorganic Chemistry Conference
    • Place of Presentation
      Kaohsiung, Taiwan
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Development of Novel Fluorescent Zinc Probe that Localizes at Plasma Membrane to Enable Site- Specific Detection of Zinc Ion2010

    • Author(s)
      Shohei Ioshi, Masayasu Taki, Yukio Yamamoto
    • Organizer
      The 5th Asian Biological Inorganic Chemistry Conference
    • Place of Presentation
      Kaohsiung, Taiwan
    • Related Report
      2010 Annual Research Report
  • [Presentation] 金属錯体を利用した活性酸素種の特異的検出法の開発2009

    • Author(s)
      水川友章・多喜正泰・山本行男
    • Organizer
      第59回錯体化学討論会
    • Place of Presentation
      長崎大学(長崎市)
    • Year and Date
      2009-09-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] 各種チオエーテル系配位子を含む銅一価蛍光プローブの開発2009

    • Author(s)
      伊吉祥平・多喜正泰・山本行男
    • Organizer
      第59回錯体化学討論会
    • Place of Presentation
      長崎大学(長崎市)
    • Year and Date
      2009-09-25
    • Related Report
      2009 Annual Research Report
  • [Presentation] 還元型フルオレセイン骨格を利用した新規銅一価蛍光センサーの開発2009

    • Author(s)
      多喜正泰・山本行男
    • Organizer
      第24回生体機能関連化学シンポジウム
    • Place of Presentation
      九州大学
    • Year and Date
      2009-09-14
    • Related Report
      2010 Final Research Report
  • [Presentation] 還元型フルオレセイン骨格を利用した新規銅一価蛍光センサーの開発2009

    • Author(s)
      多喜正泰・山本行男
    • Organizer
      第24回生体機能関連化学シンポジウム
    • Place of Presentation
      九州大学(福岡市)
    • Year and Date
      2009-09-14
    • Related Report
      2009 Annual Research Report
  • [Presentation] Ratiometric Imaging of Cadmium Ion Using A Novel Fluorescent Sensor Based on 7-Amino-4-methylcoumarin2009

    • Author(s)
      M.Taki, A.Ojida, I.Hamachi, Y.Yamamoto
    • Organizer
      14th International Conference on Biological Inorganic Chemistry
    • Place of Presentation
      名古屋国際会議場
    • Year and Date
      2009-07-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Structure and Photophysical Properties of Fluorescent Metal Sensors Containing Thioether Ligand2009

    • Author(s)
      S.Iyoshi, M.Taki, Y.Yamamoto
    • Organizer
      14th International Conference on Biological Inorganic Chemistry
    • Place of Presentation
      名古屋国際会議場
    • Year and Date
      2009-07-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] Lanthanide Complex bearing Two Zinc Complexes for Artificial Peptide Tag Recognition2009

    • Author(s)
      T.Hirayama, M.Taki, Y. Yamamoto
    • Organizer
      14th International Conference on Biological Inorganic Chemistry
    • Place of Presentation
      名古屋国際会議場
    • Year and Date
      2009-07-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] Ratiometric Imaging of Cadmium Ion Using A Novel Fluorescent Sensor Based on 7-Amino-4-methylcoumarin2009

    • Author(s)
      M.Taki, A.Ojida, I.Hamachi, Y.Yamamoto
    • Organizer
      14th International Conference on Biological Inorganic Chemistry, Nagoya (名古屋国際会議場)
    • Place of Presentation
      Japan
    • Related Report
      2010 Final Research Report
  • [Remarks] ホームページ

    • URL

      http://www.users.iimc.kyoto-u.ac.jp/~z59219/index.html

    • Related Report
      2010 Final Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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