Microsomal chemiluminescence of benzo[a]pyrene-7,8-dihydrodiol and its synthetic analogues trans- and cis-1-methoxyvinylpyrene

Ambler Thompson, W. H. Biggley, G. H. Posner, J. R. Lever, H. H. Seliger

Research output: Contribution to journalArticle

Abstract

The cis- and trans-methoxyvinylpyrene (MVP) analogues of benzo[a]pyrene-7,8-dihydrodiol (7,8-diol) produce specific microsomal chemiluminescence comparable to that produced from 7,8-diol in Aroclor-induced rat liver microsome preparations. The chemiluminescence quantum yields, emission spectra, and the concentration and the temporal kinetics of these three substrates have been examined. Radiolabelled 7,8-diol and t-MVP exhibit significant covalent binding (more than 14%) to microsomal protein when metabolized enzymatically. The extreme quenching of the dioxetane chemiluminescence by both microsomes and phosphatidylcholine, as a model phospholipid, implies that despite the low quantum yield (approx. 10-8 photons per substrate molecule) for microsomal chemiluminescence of these substrates, a significant fraction of their microsomal oxygenations may proceed via a dioxetane pathway.

Original languageEnglish (US)
Pages (from-to)210-219
Number of pages10
JournalBBA - General Subjects
Volume882
Issue number2
DOIs
StatePublished - Jun 19 1986

Keywords

  • (Microsome)
  • Benzo[a]pyrene analog
  • Chemiluminescence
  • Dioxetane
  • Methoxyvinylpyrene

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology

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