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Development of novel caged compounds that can report the yield of uncaged products

Research Project

Project/Area Number 13557209
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 医薬分子機能学
Research InstitutionThe University of Tokyo

Principal Investigator

URANO Yasuteru  The University of Tokyo, Graduate School of Pharmaceutical Sciences, Research Associate, 大学院・薬学系研究科, 助手 (20292956)

Co-Investigator(Kenkyū-buntansha) FUKASAKU Noboru  Daiichi Pure Chemicals Co., Ltd., Synthesis Technology Research Lab., General Manager (Researcher), 合成研究所, 所長(研究職)
HIROSE Kenzo  The University of Tokyo, Graduate School of Medicine, Associate Professor, 大学院・医学系研究科, 助教授 (00292730)
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥14,000,000 (Direct Cost: ¥14,000,000)
Fiscal Year 2003: ¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 2002: ¥4,000,000 (Direct Cost: ¥4,000,000)
Fiscal Year 2001: ¥6,200,000 (Direct Cost: ¥6,200,000)
KeywordsFluorescein / Caged compounds / Photoinduced Electron Tranfer / Nitrobenzyl group / 7 -Hydroxycoumarin / Marcus theory / Confocal fluorescence microscope / Photo-functional molecule / o-Nitrobenzyl基 / 計算化学 / 電荷分離状態 / レーザーフラッシュフォトリシス / o-nitrobenzyl基
Research Abstract

Fluorescence imaging is the most powerful technique currently available for continuous observation of dynamic intracellular processes in living cells. Suitable fluorescence probes are naturally of critical importance for fluorescence imaging, but only a very limited range of biomolecules can currently be visualized because of the lack of flexible design strategies for fluorescence probes. At present, design is largely empirical. We demonstrated here that the fluorescein molecule, which has been widely employed as a core of fluorescence probes, could be understood as a directly linked electron donor -fluorophore acceptor system and that the fluorescence properties of fluorescein derivatives could be controlled by intramolecular photoinduced electron tranfer. Based on these photo-physical findings, we could construct the first and totally rational design strategy for novel fluorescence probes. We could develop so far the following novel fluorescence probes; (a) DPAXs and DMAXs for singlet oxygen, (b) DAFs and DAMBOs for nitric oxide, (c) HPF and AIPF for highly reactive oxygen species including hydroxyl radical and peroxynitrite, and so on. Further, we succeeded in developing novel caged compounds that can report the yield of uncaged products as an increase of fluorescence intensity by employing a nitrobeuzyl moiety as a caging protective group and fluorescein as a reporting fluorophore.

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (26 results)

All Other

All Publications (26 results)

  • [Publications] Yu Gabe: "Highly Sensitive Fluorescence Probes for Nitric Oxide Based on Boron Dipyrromethene Chromophore. -Rational Design of Potentially Useful Bioimaging Fluorescence Probe-"J.Am.Chem.Soc.. 126. 3357-3367 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Tetsuo Miura: "Rational Design Principle for Modulating Fluorescence Properties of Fluorescein-based Probes by Photoinduced Electron Transfer"J.Am.Chem.Soc.. 125. 8666-8671 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Ken-ichi Setsukinai: "Development of Novel Fluorescence Probes That Can Reliably Detect Reactive Oxygen Species and Distinguish Specific Species."J.Biol.Chem.. 278. 3170-3175 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Noriyuki Suzuki: "Orthogonality of Calcium Concentration and Ability of 4,5-Diaminofluorescein (DAF-2) to Detect NO"J.Biol.Chem.. 277. 47-49 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kumi Tanaka: "Rational Design of Fluorescein-based Fluorescence Probes. -Mechanism-based Design of a Maximum Fluorescence Probe for Singlet Oxygen-"J.Am.Chem.Soc.. 123. 2530-2536 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yu Gabe, Yasuteru Urano, Kazuya Kikuchi, Hirotatsu Kojima, Tetsuo Nagano: "Highly Sensitive Fluorescence Probes for Nitric Oxide Based on Boron Dipyrromethene Chromophore. -Rational Design of Fluorescence Probe-"J. Am. Chem. Soc.. 126. 3357-3367 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Tetsuo Miura, Yasuteru Urano, Kumi Tanaka, Tetsuo Nagano, Kei Ohkubo, Shunichi Fukuzumi: "Rational Design Principle for Modulating Fluorescence Properties of Fluorescein-based Probes by Photoinduced Electron Transfer"J. Am. Chem. Soc.. 125. 8666-8671 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Ken-ichi Setsukinai, Yasuteru Urano, Katsuko Kakinuma, Hideyuki J. Majima, Tetsuo Nagano: "Development of Novel Fluorescence Probes That Can Reliably Detect Reactive Oxygen Species and Distinguish Specific Species"J.Biol.Chem.. 278. 3170-3175 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Noriyuki Suzuki, Hirotatsu Kojima, Yasuteru Urano, Kazuya Kikuchi, Yasunobu Hirata, Tetsuo Nagano: "Orthogonality of Calcium Concentration and Ability of 4,5-Diaminofluorescein (DAF-2) to Detect NO."J. Biol. Chem.. 277. 47-49 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kumi Tanaka, Tetsuo Miura, Naoki Umezawa, Yasuteru Urano, Kazuya Kikuchi, Tsunehiko Higuchi, Tetsuo Nagano: "Rational Design of Fluorescein-based Fluorescence Probes. -Mechanism-based Design of a Maximum Fluorescence Probe for Singlet Oxygen-"J. Am.Chem.Soc. 123. 2530-2536 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yu Gabe: "Highly Sensitive Fluorescence Probes for Nitric Oxide Based on Boron Dipyrromethene Chromophore. -Rational Design of Potentially Useful Bioimaging Fluorescence Probe-"J.Am.Chem.Soc.. (印刷中). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Tetsuo Miura: "Rational Design Principle for Modulating Fluorescence Properties of Fluorescein-based Probes by Photoinduced Electron Transfer"J.Am.Chem.Soc.. 125. 8666-8671 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Ken-ichi Setsukinai: "Development of Novel Fluorescence Probes That Can Reliably Detect Reactive Oxygen Species and Distinguish Specific Species."J.Biol.Chem.. 278. 3170-3175 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 浦野泰照: "光誘起電子移動理論に基づく蛍光プローブの精密設計"ぶんせき. 426-432 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 長野哲雄: "活性酸素イメージングプローブ"実験医学. 21. 2144-2146 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Kenjiro Hanaoka: "Selective Detecting of Zinc Ions with Novel Luminescent Lanthanide Probes"Angewandte Chemie, Int.Ed.. 42. 2996-2999 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Ken-ichi Setsukinai: "Development of Novel Fluorescence Probes That Can Reliably Detect Reactive Oxygen Species and Distinguish Specific Species"J.Biol.Chem.. 278(印刷中). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Motohiro Nishida: "Gi and Go as a redox sensor"J.Biol.Chem.. 277. 9036-9042 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Satoko Maruyama: "A Novel, Cell-Permeable, Fluorescent Probe for Ratiometric Imaging of Zinc Ion"J.Am.Chem.Soc.. 124. 10650-10651 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 浦野 泰照: "PET理論と蛍光プローブ"現代化学. 381. 44-50 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Tomoya Hirano: "Improved Fluorescent Probes for Zinc, ZnAFs, Suitable for Biological Applications"J.Am.Chem.Soc.. 124. 6555-6562 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Hideo Takakusa: "Design and Synthesis of an Enzyme-Cleavable Sensor Molecule for Phosphodiesterase Activity Based on Fluorescence Resonance Energy Transfer"J.Am.Chem.Soc.. 124. 1653-1657 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Kumi Tanaka: "Rational Design of Fluorescein-based Fluorescence Probes. -Mechanism- based Design of a Maximum Fluorescence Probe for Singlet Oxygen-"J. Am. Chem. Soc.. 123. 2530-2536 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Mitsuo Wada: "Synthesis and Optical Properties of a New Class of Pyrromethene-BF2 complex Fused with Rigid Bicycle Rings and Benzo Derivatives"Tetrahedron Lett.. 42. 6711-6713 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Noriyuki Suzuki: "Orthogonality of Calcium Concentration and Ability of 4, 5-Diaminofluorescein(DAF-2)to Detect NO"J.Bjol.Chem.. 277. 47-49 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] 浦野 泰照: "高感度一重項酸素蛍光プローブの開発"医学のあゆみ、別冊"酸化ストレス". 131-134 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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