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1995 Fiscal Year Final Research Report Summary

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
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.

  • Research Products

    (25 results)

All Other

All Publications (25 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
  • [Publications] T.Hirano: "Chemi- and Bio-luminescence Properties of Coelenterazine Analogues Possessing an Adamantyl Group" J.Chem.Soc.,Chem.Commun.1135-1136 (1995)

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  • [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)

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

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

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  • [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)

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  • [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)

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

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  • [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)

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  • [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)

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  • [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)

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

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  • [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)

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

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  • [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)

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

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

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

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  • [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)

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  • [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)

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

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  • [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)

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

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  • [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)

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

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Published: 1997-03-04  

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