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Study on the control of excitation and alleviation in chemiluminescence reaction on the basis bioluminescence

Research Project

Project/Area Number 11660106
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionMie University

Principal Investigator

TERANISHI Katsaunori  Mie University, Bioresources, Associate Professor, 生物資源学部, 助教授 (20237001)

Project Period (FY) 1999 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2001: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 2000: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1999: ¥2,400,000 (Direct Cost: ¥2,400,000)
KeywordsChemiluminescence / 発光プローブ
Research Abstract

Chemiluminescence compound 2-methyl-6-(4-methoxyphenyl)imidazo[1,2 - α]pyrazin-3(7H)-one (MCLA) was attached to cyclomaltooligosaccharides (cyclodextrins) by the formation of an amide bond. The properties of oxygen-induced chemiluminescence of the synthesized cyclodextrin-bound MCLA were investigated in pH 8.0 aqueous phosphate buffer. The light-emitting efficiency was remarkably dependent n the kibnd of bounhd cyclodextrin, chain length between the MCLA and cyclodextrin, and the binding site in cyclodextrin. The light-emitting efficiencies of cyclomaltooctaose (γ-cyclodextrin)-bound compounds were higher than that of cyclomaltohexaose or cyclomaltoheptaose-bound compounds. Especially a compound in which MCLA attached to the secondary side of γ-cyclodextrin through short chain showed an up to 44 -fold enhancement over that of a non-cyclodextrin compound. In the present case, the efficiency of excited singlet state formation was 23-fold grater than that of the non-cyclodextrin compound and significantly contributed to the grater light-emitting efficiency. Induced circular dichroism spectra indicated the wide entrance of the secondary side of γ-cyclodextrin and short chain allow strong intramolecular affinity of the light-emitting chromophore and the cycrodextrin.

Report

(4 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (37 results)

All Other

All Publications (37 results)

  • [Publications] K.Teranishi: "Regioselective 2^A, 2^D-disulfonyl capping of β-cyclodextrin for practical bifunctiesclization on the secon day hydroxyl pure"Tetrahedron Lett.. 42. 5477-5480 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Teranishi: "Synthesis and chemiluminescence properties in an a***ese solution of cyclodextrin 6-(4-Methoxyphenyl)-2-methylimidazo[1,2-a]pyrazin-3(7H)-one"ITE Letters on Batteries, New Technologies & Medie one. 2. 530-536 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Teranishi: "Effect of confornation on the chemiluminescene efficiency of light producing 2-methyl-6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-ones"Luminescience. 16. 367-374 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Teranishi, T.Nishiguchi: "Regroselective punctionalization of the secondary side of cyclo****** (d-cyclodexytrin)"ITE Letters, on Batteries, New Technologies & medicine. 3(in press). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Teranishi, F.Ueno: "Regioselective silylation of C-2 hydroxyl group of alpha-cyclodextrin dependent on reaction temperature"Tetrahedron Lett.. (in press). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Teranishi: "Direct regioselective 2-O-(p-toluenesulfonylation) of sucrose"Carbohydr. Res.. (in press). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi, S. Tanabe, M. Hisamatsu, T. Yamada: "Investigation of cyclomaltooligosaccharide-bound 6-(4-methoxyphenyl) imidazole-[1-2-a]pyrazin-3(7H)-one for enhanced chemiluminescence"Luminescence. 14. 303-314 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi, M. Hisamatsu, T. Yamada: "Chemiluminescence of 2-methyl-6-arylimidazo[1,2-a]phyrazin-3(7H)-one in protic solvents : electron-donating substituent effect on the formation of the neutral singlet excited molecule"Luminescence. 14. 297-302 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi, M. Hisamatsu, T. Yamada: "Regiospecific Syntheses of 2A,2B-Disulfonated γ-Cyclodextrin"Tetrahedron Lett.. 41. 933-936 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] O. Shimomura, K. Teranishi: "Light-emitters involved in the luminescence of coelenterzine"Luminescence. 15. 51-58 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi, S. Tanabe: "Regiospecific Alkylation Dependent on Alkyl Chain Length of N-Bromoalkylphthalimides and an Efficient Preparation of 2-ο-Aminoalkyl Cyclomaltooligosaccharides (Cyclodextrins)"ITE Letters on Batteries, New Technologies & Medicine. 1. 53-60 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J. F. Head, S. Inouye, K. Teranishi, O. Shimomura: "The crystal structure of the photoprotein aequorin at 2.3 A resolution"Nature. 405. 372-376 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi: "Practicable regiospecific bifunctionalization o the secondary face of α- and β-cyclodextrins"J. Chem. Soc., Chem. Commun.. 1255-1256 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi: "Regiospecific 2_A,2_C-Disulfonation of β-Cyclodextrin"Tetrahedron Lett.. 41. 7085-7088 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Mishima, K. Teranishi, T. Yamada, M. Hisamatsu: "Correlation between annaled schizophyllan's conformation detected by circular dichroism and physical and physiological activities"ITE Letters on Batteries, New Technologies & Medicine. 1. 956-961 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Yamada, Y. Fujimoto, T. Adachi, M. Hisamatsu, K. Teranishi: "Air oxidation of cyclodextrin with a platinum catalyst"J. Appl. Glycosci.. 47 (1). 21-26 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi: "Regioselective 2_A,2_D-disulfonyl capping of β-cyclodextrin for practical bifunctionalizaion on the secondary hydroxyl face"Tetrahedron Lett.. 42. 5477-5480 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi: "Synthesis and chemiluminescence properties in an aqueous solution of cyclodextrin-bound 6-(4-methoxyphenyl)imidazo[1,2-α]pyrazin-3(7H)-one"ITE Letters on Batteries, New Technologies & Medicine. 2. 530-536 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi: "Effect of conformation on the chemiluminescence efficiency of light-producing 2-methyl-6(4-methoxyphenyl)imidazo[a,2-α]pyrazin-3(7H)-ones"Luminescence. 16. 367-374 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi, T. Nishiguchi, H. Ueda: "Regioselective functionalization of the secondary side of cyclomaltononaose (δ-cyclodextrin)"ITE Letters on Batteries, New Technologies & Medicine. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi, F. Ueno: "Regioselective silylation of C-2 hydroxyl group of α-cyclodextrin dependent on reaction temperature"Tetrahedron Lett. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Teranishi: "Direct regioselective 2-O-(p-toluenesulfonylation) of sucrose"Carbohydr. Res.. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Teranishi: "Regioselective 2^A,2^D-disulfonyl Copping of A-cyclodextrin for practical bifunctional cantion on the serondry thydroed tare"Tetrahedron Lett.. 42. 5477-5480 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Teranishi: "Synthesis and chemiluminescence properties in an agaeoas solution of cyclodextrin-bousd 6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one"Letters on Batteries,New Technologies & Medicine. 2. 530-536 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Teranishi: "Effect of conformation on the chemiluminescence efficiency of light-producing 2-methyl-6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-ones"Luminescence. 16. 367-374 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Teranishi, T.Nishiguch, H.Ueda: "Regioselective functionalization of the secondary side of cyclomaltononaose (d-cyclodextrin)"Letters on Batteries,New Technologies & Medicine. 3(in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Teranishi F.Ueno: "Regioselective silylation of c-2hxdroxygroup of α-cydrotion dependent on reaction tenperature"Tetrahedron Lett.. (in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Teranishi: "Direct regioselective 2-O-(p-toluenesulfonylation)of sucrose"Carbohydr.Res.. (in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Katsunori Teranishi: "Regiospecific Synthesis of 2A, 2B-Disulfonated γ-Cyclodextrin"Tetrahedron Letters. 41. 933-936 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Katsunori Teranishi: "Regiospecific Alkylation Dependent on Alkyl Chain Length of N-Bromoalkylph alimides and an Efficient Preparation of 2-0-Aminoalkyl Gdoma Hodiosaccharides"ITE Letteres on Buteries New Te chndogiesg Medicine. 1. 53-60 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Katsunori Teranishi: "Practicable regiospecific bifunctionalization on the seconday face of α-and β cyclodextrin"J.Chem.Soc.Chem.Commun.. 1255-1256 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Kastunori Teranishi: "Regiospecific 2^4,2^c-Disulfonation of β-cyclodextrin"Tetrahedron Letters. 41. 7085-7088 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Osamu Shimomura: "Light-emitters involved in the luminescence of coelenterazin"Luminescence. 15. 51-58 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] James.F Head: "The crystal structure of the photoprotein aequorin at 2.3A resolution"Nature. 405. 372-376 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Katsunori Teranishi: "Chemiluminescence of 2-methyl-6-arylimidazo[1,2-a]pyrazin-3(7H)-one in protic solvents : electron-donating substituent effect on the formation of the neutral singlet excited molecule"Luminescence. 14. 297-302 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Katsunori Teranishi: "Investigation of cyclomaltooligosaccharide-bound 6-(4-methoxyphenyl)imidazole[1,2-a]pyrazin-3(7H)-one for enhanced chemiluminescence"Luminescence. 14. 303-314 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Katsunori Teranishi: "Regiospecific Synthesis of 2A,2B-Disulfonated γ-Cyclodextrin"Tetrahedron Lett.. (in press).

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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