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Development of Conceputually New Photonics Materials Based on New Luciferins

Research Project

Project/Area Number 14580608
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionThe University of Electro-Communications

Principal Investigator

NIWA Haruki  The University of Electro-Communications, Faculty of Electro-Communications Applied Physics and Chemistry, Professor, 電気通信学部, 教授 (20135297)

Co-Investigator(Kenkyū-buntansha) HIRANO Takashi  The University of Electro-Communications, Faculty of Electro-Communications Applied Physics and Chemistry, Associate Professor, 電気通信学部, 助教授 (20238380)
MAKI Shojiro  The University of Electro-Communications, Faculty of Electro-Communications Applied Physics and Chemistry, Research Associate, 電気通信学部, 助手 (20266349)
Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2003: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2002: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsBioluminescence / Odontosyllis / Plocamopherus imperialis / Mycea chlorophos / luciferin / luciferase / firefly / imidazopilazinone / 発光生物 / ヨコスジタマキビモドキ / アミノピラジン / Odontosyllis / 単離
Research Abstract

Molecular basis of light emitting system of various bioluminescent organisms were investigated. The bioluminescence system of the marine sea fire worm Odontosyllis undecimdonta was found to exhibit typical luciferin-luciferase reaction. The luciferin was found to be able to extract with methanol, and the luciferase with hot water. The emition of bluewish green light was observed by mixing the methanol extract and the water extract. The isolation of luciferin from the methanol extract was attempted by using HPLC, and we found that the luciferin to be acidic substance(s) with high polarity. Owing to low quantity of the luciferin content, we could not determine the chemical structure so far.
The bioluminescence system of the sea hare Plocamopherus imperialis was found also o exhibited luciferin-luciferase reaction. The sample was found to keep the bioluminescence ability even after storing at low temperature (below-80℃) for years.
In connection of exploration of bioluminescence system of th … More e mushroom Mycea chlorophos, we isolated basidiospores from the fruit-body of the mushroom collected from Hatijuo Island. The basidospores were germinated, from which a single strain of the fruiting mycelium was isolated. Using the single strain of the fruiting mycelium, we succeeded laboratory cultivation of fruiting body. We attempted the isolation of fluorescent substance(s) with the maximum around green light(510nm), resulting to the identification of lumichrom.
In the course of the construction of Bioluminescence Resonance Energy Transfer (BRET) system utilizing the firefly bioluminescence system coupled with Aequorea green fluorescence protein (GFP), the molecular design of blue light-producing firefly luciferin analogs was performed. After brief studies on the structure-bioluminescence activity relation ship, we succeeded the synthesis of an analog having a bioluminescence maximum shorter than that of native firefly luciferin.
In connection with the development of new photonics materials based on bioluminescence systems, we succeeded new imidazopilazinone derivatives with extended π-systems. Less

Report

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

    (20 results)

All 2005 2004 2003 2002 Other

All Journal Article (14 results) Book (1 results) Patent(Industrial Property Rights) (2 results) Publications (3 results)

  • [Journal Article] Bioluminescence Activity of Latia Luciferin Analogues : Replacement of the 2,6,6-Trimethylcyclohexene Ring into the Methyl-substituted Phenyl Groups2005

    • Author(s)
      Mitsuhiro Nakamura
    • Journal Title

      Tetrahedron Letters Vol. 46

      Pages: 53-56

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Metal-ion Complexation of Imidazo[1,2-a]pyrazin-3(7H)-ones : Continous Change in Absorption Spectra of Complexs Depending on the Lewis Acidity of the Metal Ion2004

    • Author(s)
      Takashi Sekiguchi ら
    • Journal Title

      Chemistry Letters Vol. 33

      Pages: 1484-1485

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Regioselective phenyl-substitution effects on the solvatochromism of 2-phenylimidazo[1,2-a]pyrazin-3(7H)-one derivatives : Expansion of the color variation range of a visible-indicator for the proton donor ability of solvents2004

    • Author(s)
      Shunsuke Fujio ら
    • Journal Title

      Tetrahedron Letters Vol. 45

      Pages: 8531-8534

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Substituent Effects on the Solvatochromism of 2-Phenylimidazopyrazinones : Effective Control of the Color Variation Range and Sensitivity toward an Indication of the Proton-Donor Ability of Solvents by an Electron-withdrawing Group Substitutionsolvents2004

    • Author(s)
      Yoshiharu Takamuki ら
    • Journal Title

      Chemistry Letters Vol. 33

      Pages: 1484-1485

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Synthesis of Latia Luciferin Benzoate Analogues and those Bioluminescent Activity2004

    • Author(s)
      Mitsuhiro Nakamura
    • Journal Title

      Tetrahedron Letters Vol. 45

      Pages: 2203-2205

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Metal-ion Complexation of Imidazo[1,2-a]pyrazin-3(7H)-ones : Continous Change in Absorption Spectra of Complexs Depending on the Lewis Acidity ofthe Metal Ion.2004

    • Author(s)
      Takashi Sekiguchi, Shojiro Maki, Haruki Niwa, Hiroshi Ikeda, Takashi Hirano.
    • Journal Title

      Tetrahedron Letters 45,No.5

      Pages: 1065-1069

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Synthesis of Latia Luciferin Benzoate Analogues and those Bioluminescent Activity.2004

    • Author(s)
      Mitsuhiro Nakamura, Mizuki Masaki, Shojiro Maki, Ryo Matsui, Minako Hieda, Masashi Mamino, Takashi Hirano, Yoshihiro Ohmiya, Haruki Niwa
    • Journal Title

      Tetrahedron Letters 45,No.10

      Pages: 2203-2205

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Regioselective phenyl-substitution effects on the solvatochromism of 2-phenylimidazo[1,2-a]pyrazin-3(7H)-one derivatives : Expansion on the color variation range of a visible-indicator for the proton donor ability of solvents.2004

    • Author(s)
      Shunsuke Fujio, Daisuke Hashizume, Yoshiharu Takamuki, Masanori Yasui, Fujiko Iwasaki, Shojiro Maki, Haruki Niwa, Hiroshi Ikeda, Takashi Hirano
    • Journal Title

      Terahedron Lett. 45,No.46

      Pages: 8531-8534

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Substituent Effects on the Solvatochromism of 2-Phenylimidazopyrazinones : Effective Control of the Color Variation Range and Sensitivity toward an Indication of the Proton-Donor Ability of Solvents by an Electron-with drawing Group Substitution.2004

    • Author(s)
      Yshiharu Takamuki, Shojiro Maki, Haruki Niwa, Hiroshi Ikeda, Takashi Hirano.
    • Journal Title

      Chemistry Lett. 33,No.11

      Pages: 1484-1485

    • NAID

      10013772077

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Fundamental Studies on The Structure and Spectroscopic Properties of 3,7-Dihydroimidazo[1,2-a]pyrazin-3-one Derivatives2003

    • Author(s)
      Shunichiro Nakai ら
    • Journal Title

      Bull.Chem.Soc.Jpn., Vol. 76

      Pages: 2361-2387

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Fundamental Studies on The Structure and Spectroscopic Properties of 3,7-Dihydroimidazo[1,2-a]pyrazin-3-one Derivatives.2003

    • Author(s)
      Shunnichiro Nakai, Masanori Yasui, Masaki Nakazato, Fujiko Iwasaki, Shojiro Maki, Haruki Niwa, Mamoru Ohashi, Takashi Hirano.
    • Journal Title

      Bull.Chem.Soc.Jpn. 76,No.12

      Pages: 2361-2387

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Viscosity Dependent Fluorescence Decay of the GFP Chromophore in Solution Due to Fast Internal Conversion..2002

    • Author(s)
      A.D.Kummer ら
    • Journal Title

      J.Physical Chem.B Vol. 50

      Pages: 52-57

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] 生物発光のメカニズムとその応用2002

    • Author(s)
      丹羽治樹
    • Journal Title

      現代化学 No.379

      Pages: 28-36

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Journal Article] Viscosity Dependent Fluorescence Decay of the GFP Chromophore in Solution Due to Fast Internal Conversion.2002

    • Author(s)
      Andreas D.Kummer, Christian Kompa, Haruki Niwa, Takashi Hirano, Satoshi Kojima, Maria Elisabeth Michel-Beyerle.
    • Journal Title

      J.Physical Chem.B 106,No.30

      Pages: 7554-7559

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Book] ライフサイエンス化学2003

    • Author(s)
      新井孝夫 ら
    • Total Pages
      304
    • Publisher
      東京化学同人
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 複素環化合物及び発光甲虫ルシフェラーゼ発光系用発光物質2005

    • Inventor(s)
      丹波 治樹, 牧 昌次郎, 平野 誉
    • Industrial Property Rights Holder
      電通大
    • Industrial Property Number
      2005-031574
    • Filing Date
      2005-02-08
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 天然型L-システインまたはその誘導体を用いたホタル発光基質の生合成システム及び本システムを含んだ発光基質溶液2004

    • Inventor(s)
      近江谷 克裕, 丹波 一樹, 丹波 治樹, 中村 光裕, 龍福 正行
    • Industrial Property Rights Holder
      産総研, 電通大, 東洋ビーネット
    • Industrial Property Number
      2004-379971
    • Filing Date
      2004-12-28
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Itoh: "Reduction in Desorption Mass Spectrometry : Multiple Protonation on Flavins without Charge Increment"J. Mass Spectrom. Jpn.. 50,No.2. 52-57 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] A.D.Kummer: "Viscosity Dependent Fluorescence Decay of the GFP Chromophore in Solution Due to Fast Internal Conversion"J. Physical Chem. B. 106,No.30. 7554-7559 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 丹波治樹: "生物発光のメカニズムとその応用"現代化学. No.379. 28-36 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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