Imidazopyrazinone bio- and chemiluminescence mechanism: the chemiexcitation process in bioluminescence

DOI

Bibliographic Information

Other Title
  • イミダゾピラジノン生物・化学発光系の反応機構：生物発光の化学励起過程

Abstract

Bioluminescence of the ostracod Cypridina (Vargula) and the jellyfish Aequorea gives a high quantum yield of light production. This indicates that the chemiexcitation process in the bioluminescence reaction produces an excited molecule with a high efficiency. These bioluminescent systems use imidazopyrazinone (imidazo[1,2-a]pyrazin-3(7H)-one) compounds as the bioluminescence substrates, Cypridina luciferin and coelenterazine, respectively. To establish the chemiexcitation mechanism of the bioluminescence, we investigated the chemiluminescence of a series of 6-arylimidazopyrazinones as a bioluminescence model system. In addition, we investigated the fluorescent properties of the light-emitter compounds (amidopyrazines) and carried out DFT calculations of the molecules related to the chemiexcitation process. From these results, we propose the mechanism for the highly efficient chemiexcitation in the Cypridina and Aequorea bioluminescence: thermal decomposition of a neutral dioxetanone intermediate having an electron-donating substituent gives the singlet-excited state (S1) of a light-emitter molecule with a strong intramolecular charge transfer (ICT) character via an ICT transition state (TS) [ICT TS->S1 route in the charge transfer induced luminescence (CTIL) mechanism].

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Details 詳細情報について

  • CRID
    1390001205555820160
  • NII Article ID
    130004645464
  • DOI
    10.11494/kisoyuki.2008.0.335.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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