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

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.