• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Fundamental Research on Chemi-and Bioluminescence for High-Efficiency Light Emission

Research Project

Project/Area Number 06303003
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionOchanomizu University

Principal Investigator

MAEDA Koko  Ochanomizu Univ., Dept.of Chemistry, Professor, 理学部, 教授 (40017190)

Co-Investigator(Kenkyū-buntansha) IMAI Kazuhiro  The University of Tokyo, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (50012620)
MATSUMOTO Masakatsu  Kanagawa Univ., Dept.of Chemistry, Professor, 理学部, 教授 (10260986)
KIMURA Masaru  Okayama Univ., Dept.of Chemistry, Associate Professor, 理学部, 助教授 (30033442)
ISOBE Minoru  Nagoya Univ., Lab.of Organic Chemistry , Professor, 農学部, 教授 (00023466)
OHASHI Mamoru  The University of Electro-Communications, Dept.of Applied Physics and Chemistry,, 電気通信学部, 教授 (70015535)
Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥4,200,000 (Direct Cost: ¥4,200,000)
Fiscal Year 1995: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1994: ¥2,400,000 (Direct Cost: ¥2,400,000)
Keywordschemiluminescence / bioluminescence / emission efficiency / coelenterazine / dioxetane / Iuciferin / mechanism of luminescence / electron-transfer emission
Research Abstract

In the chemiluminescence and bioluminescence, the light emission is brought out from an excited state of carbonyl compounds formed by thermal decomposition of unstable intermediates, such as dioxetanes in the former and dioxetanones in the latter, respectively. The mechanism of the thermal decomposition to give an excited state of carbonyl compounds is still unclear, because the concerted way leads to a triplet state which gives only weak emission. Schuster reported CIEEL mechanism which contains intramolecular electron transfer, but recently the idea was found not to explain some experimental facts.In this research the oxygenation mechanism of chemi-and bio-luminescent compounds and thermal decomposition mechanism of dioxetanes were investigated. The results obtained are as follows : The oxygenation of imidazopyrazinone which is a main part of luciferins was carried out, and the structure of the dioxetanone was determined. Various derivatives of lophine (2,4,5-triphenylimidazol) were prepared and a structural condition which has very high quantum yield (0.8) was found, and involvement of the intramolecular electron transfer was suggested. Compounds which have electron rich olefinic structure, for example the reduced species of biisoquinolinium salts were found to react with molecular oxygen and/or superoxide. For newly prepared 3-aryl dioxetanes which decompose at room temperature to give emission, the conformation of the aryl group to the dioxetane ring was shown to have strong effect on the emission intensity and on the stability of the dioxetanes.

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (59 results)

All Other

All Publications (59 results)

  • [Publications] K.Maeda: "Mechanism of the chemiluminescence of biisoquinolinium salts" J.Chem.Soc.,Perkin Trans.2. 121-126 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] T.Hirano: "Chemi- and Bio-luminescence Properties of Coelenterazine Analogues Possessing an Adamantyl Group" J.Chem.Soc.,Chem.Commun.1135-1136 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] F.Q.Chen: "A potential photoaffinity probe for labelling the active site of aequorin : a photolabile coelenterazire analogue with a trifluoromethyldiazirine group" J.Chem.Soc.,Perkin Trans.1. 2129-2134 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] T.Matsuno: "Mass Spectrometric Investigation of Structures of Intermediates in Acridine Chemiluminescence" J.Mass Spectrom.Soc.,Jpn.(in press.). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Isobe: "New Analysis Method for Protein Phosphatase Type 2A Inhibitors Using the Firefly Bioluminescence System" Biosci.Biotech.Biochem.59. 2235-2238 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Ohto: "Involvement of Ca^<2+>-signaling in the sugar-inducible expression of genes coding for sporamin and β-amylase of sweet potato" The Plant Journal. 7. 297-307 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K,Teranishi: "Efficient preparation of alkoxymethyl carbonates by using potassium carbonate,chloromethyl alkyl ethers and alcohols" Bull.Chem.Soc.Jpn.68. 309-314 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Teranishi: "One-step synthesis of novel carbonate,alkoxymethyl carbonate,from alcohol and chloromethyl alkyl ether using silver carbonate" Synthesis. 176-180 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Satake: "Rearrangement of Bicycol[2.2.2]octa-2,5-diene and Bicyclo[3.2.2]nona-6,8-diene under the Conditions of Bromination" Bull.Chem.Soc.Jpn.69(in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Okamoto: "Characterization of a Longicyclic[2,2,2,2]conjugated π System in 1,4-Difluorobenzene-Naphthalene Biplanemer" Bull.Chem.Soc.Jpn.68. 3557-3562 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Matsumoto: "Effect of allylic oxygen on the reaction pathways of singlet oxygenation : selective formation of 1,2-dioxetanes from 1-alkoxymethyl-2-aryl-1-tert-butyl-2-methoxyethylenes" Tetrahedron Lett.37(in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Matsumoto: "Synthesis and chemiluminescence of 3-biphenylyl-4,4-diisopropyl-3-methoxy-1,2-dioxetanes" Heterocycles. 41. 2419 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Usami: "Two Luminescent Intermediates of Coelenterazine Analog,Peroxide and Dioxetanone,Prepared by Direct Photooxygenation at Low Temperature" Tetrahedron Lett.36. 8613-8616 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Usami: "Chemiluminescent Characters of Hydroperoxide and Dioxetanone of Coelenterate Luciferin Analog Prepared by LOw-Temperature Photooxygenation" Chem.Lett.(in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.-C.Rho: "Zooxanthellatoxin-A,a novel polyoxygenated long chain compound,activated rabbit platelets,mediated via Ca^<2+> influx followed by the release of thromboxane A2 in an external Ca^<2+>-dependent manner" Br.J.Pharmacol.(in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Nakamura: "Synthesis of 5-and 3,5-Substituted 2-Amino-pyrazines by Pd Mediated Still Coupling" Synlett. 1277-1278 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Nakamura: "Zooxanthellatoxin-A,a Potent Vasoconstrictive 62-membered Lactone from a Symbiotic Dinoflagellate" J.Am.Chem.Soc.117. 550-551 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Teranishi: "Synthesis of a model for the functional part of photoprotein aequorin" Biosci.Biotech.Biochem.59. 104-107 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Matsumoto: "Thermal stability and chemiluminescence of 3-alkoxy-3-aryl-4,4-diisopropyl-1,2-dioxetanes" J.Chem.Soc.,Chem.Commun.431-432 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Kitamura: "A new highly sensitive chemiluminescent assay of alkaline phosphatase using lucigenin and its application to enzyme immunoassay" J.Biolumin.Chemilumin.10. 1-7 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Sasamoto: "Chemiluminescent enzymatic assay for cholesterol in serum using lucigenin" Anal.Chim.Acta. 310. 347-353 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Sasamoto: "Highly sensitive immunological assays for human chorionic gonadotropin and prostatic acid phosphate using phenacyl phosphate as chemiluminescent label" Anal.Chim.Acta. 309. 221-225 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Tsuji: "Recent advances of chemiluminescent and bioluminescent assay" Jpn.J.Electroph.39. 301-309 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] P.Prados: "Generation of an active intermediate during the storage of a peroxyoxalate chemiluminescence reagent solution under the presence of strong carboxylic acids" Anal.Sci.11. 575-580 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Tsuji: "Nonisotopic Probing,Blotting and Sequencing" Academic Press Inc., 10 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Maeda: "Mechanism of the chemiluminescence of biisoquinolinium salts" J.Chem.Soc.,Perkin Trans.2. 121-126 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] T.Hirano: "Chemi-and Bio-luminescence Properties of Coelenterazine Analogues Possessing an Adamantyl Group" J.Chem.Soc.,Chem.Commun.1135-1136 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] F.Q.Chen: "A potential photoaffinity probe for labelling the active site of aequorin:a photolabile coelenterazire analogue with a trifluoromethyldiazirine group" J.Chem.Soc.,Perkin Trans.1. 2129-2134 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] T.Matsuno: "Mass Spectrometric Investigation of Structures of Intermediates in Acridine Chemiluminescence" J.Mass Spectrom.Soc.,Jpn.(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Isobe: "New Analysis Method for Protein Phosphatase Type 2A Inhibitors Using the Firefly Bioluminescence System" Biosci.Biotech.Biochem.59. 2235-2238 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Ohto: "Involvement of Ca^<2+>-signaling in the sugar-inducible expression of genes coding for sporamin and β-amylase of sweet potato" The Plant Journal. 7. 297-307 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Teranishi: "Efficient preparation of alkoxymethyl carbonates by using potassium carbonate,chloromethyl alkyl ethers and alcohols" Bull.Chem.Soc.Jpn.68. 309-314 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Teranishi: "One-step synthesis of novel carbonate,alkoxymethyl carbonate,from alcohol and chloromethyl alkyl ether using silver carbonate" Synthesis. 176-180 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Satake: "Rearrangement of Bicyclo[2.2.2]octa-2,5-diene and Bicyclo-[3.2.2]nona-6,8-diene under the Conditions of Bromination" Bull.Chem.Soc.Jpn.69(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Okamoto: "Characterization of a Longicyclic[2,2,2,2]conjugated π System in 1,4-Difluorobenzene-Naphthalene Biplanemer" Bull.Chem.Soc.Jpn.68. 3557-3562 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Matsumoto: "Effect of allylic oxygen on the reaction pathways of singlet oxygenation:selective formation of 1,2-dioxetanes from 1-alkoxymethyl-2-aryl-1-tert-butyl-2-methoxyethylenes" Tetrahedron Lett.37(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Matsumoto: "Synthesis and chemiluminescence of 3-biphenylyl-4,4-diisopropyl-3-methoxy-1,2-dioxetanes" Heterocycles. 41. 2419 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Usami: "Two Luminescent Intermediates of Coelenterazine Analog,peroxide and Dioxetanone,Prepared by Direct Photooxygenation at Low Temperature" Tetrahedron Lett.36. 8613-8616 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Usami: "Chemiluminescent Characters of Hydroperoxide and Dioxetanone of Coelenterate Luciferin Analog Prepared by Low-Temperature Photooxygenation" Chem.Lett.(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.-C.Rho: "Zooxanthellatoxin-A,a novel polyoxygenated long chain compound,activates rabbit platelets,mediated via Ca^<2+> influx followed by the release of thromboxane A2 in an external Ca^<2+>-dependent manner" Br.J.Pharmacol.1996 ((in press))

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Nakamura: "Synthesis of 5-and 3,5-Substituted 2-Amino-pyrazines by Pd Mediated Still Coupling" Synlett. 1277-1278 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Nakamura: "Zooxanthellatoxin-A,a Potent Vasoconstrictive 62-membered Lactone from a Symbiotic Dinoflagellate" J.Am.Chem.Soc.117. 550-551 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Teranishi: "Synthesis of a model for the functional part of photoprotein aequorin" Biosci.Biotech.Biochem.59. 104-107 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Matsumoto: "Thermal stability and chemiluminescence of 3-alkoxy-3-aryl-4,4-diisopropyl-1,2-dioxetanes" J.Chem.Soc.,Chem.Commun.431-432 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Kitamura: "A new highly sensitive chemiluminescent assay of alkaline phosphatase using lucigenin and its application to enzyme immunoassay" J.Biolumin.Chemilumin.10. 1-7 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Sasamoto: "Chemiluminescent enzymatic assay for cholesterol in serum using lucigenin" Anal.Chim.Acta. 310. 347-353 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Sasamoto: "Highly sensitive immunological assays for human chorionic gonadotropin and prostatic acid phosphate using phenacyl phosphate as chemiluminescent label" Anal.Chim.Acta. 309. 221-225 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Sasamoto: "Chemiluminescent assay of alkaline phosphatase using phenacvl phosphate" Anal.Chim.Acta. 306. 161-165 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.Tsuji: "Recent advances of chemiluminescent and bioluminescent assay" Jpn.J.Electroph.39. 301-309 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] P.Prados: "Generation of an active intermediate during the storage of a peroxyoxalate chemi-luminescence reagent solution under the presence of strong carboxylic acids" Anal.Sci.11. 575-580 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 中村英士: "有機化学からみた渦鞭毛藻" 藻類. 43. 23-30 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 前田昌子: "化学発光エンザイムイムノアッセイの原理と実際" 日本臨床. 53. 2096-2099 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.Tsuji: "Nonisotopic Probing,Blotting and Sequencing" Academic Press Inc., 10 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] T.Hirano et al.: "Revision of the Structure of the Light-emitter in Aequorin Bioluminescence" J.Chem.Soc.,Chem.Commun.165-167 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Inouye & H.Nakamura: "Stereospecificity in hydride transfer and substrate specificity for FMN-containing NAD(P)H-flavin oxidoreductase from the luminescent bacterium" Biochem.Biophys Res.Commun.205. 275-281 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Takahashi & M.Isobe: "Photoprotein of Luminous Squid,Symplectoteuthius oualaniensis and Reconstruction of the Luminous System" Chem.Lett.843-846 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Isobe et al.: "Bioluminescence mechanism on new systems" Pure and Applied Chemistry. 66. 765-772 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Kimura: "The Chemiluminescent Cycloreversion of an Anthracene-Benzene Biplanemer System Both in the Solid State and in the Liquid State" Bull.Chem.Soc.Jpn.67. 2203-2212 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Mitani et al.: "Determination of Horseradish Peroxidase Concentration Using the Chemiluminescence of Cypridina Luciferin Analogue,2-Methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2a]pyrazin-3-one" J.Biolumin.Chemilumin.9. 455-461 (1994)

    • Related Report
      1994 Annual Research Report

URL: 

Published: 1994-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi