IDENTIFICATION OF MUTAGENIC DIHYDRODIOLS AS METABOLITES OF BENZO(J)FLUORANTHENE AND BENZO(K)FLUORANTHENE

  • 1 January 1980
    • journal article
    • research article
    • Vol. 40  (12) , 4528-4532
Abstract
The metabolism of the [carcinogenic] environmental agents benzo(j)-fluoranthene and benzo(k)fluoranthene was investigated using supernatants from the livers of Aroclor 1254-pretreated rats, which are effective in activating benzo(j)fluoranthene and benzo(k)fluoranthene to metabolites mutagenic toward Salmonella typhimurium TA 100. Six bands of metabolites of benzo(j)fluoranthene were separated by high-pressure liquid chromatography, and each band was tested for mutagenicity toward S. typhimurium TA 100 with activation. The major mutagenic band contained 2 dihydrodiols, 1 of which was identified as 9,10-dihydro-9, 10-dihydroxybenzo(j)fluoranthene by comparison to a synthetic reference standard. 9,10-Dihydro-9,10-dihydroxybenzo(j)fluoranthene was mutagenic toward S. typhimurium TA 100 with activation, presumably as a result of conversion to the corresponding dihydrodiol-epoxide. The major dihydrodiol metabolite of benzo(k)fluoranthene was identified, by comparison to a synthetic standard, as 8,9-dihydro-8,9-dihydroxybenzo(k)fluoranthene. This dihydrodiol, which could be converted to a dihydrodiol-epoxide, was mutagenic toward S. typhimurium TA 100 with activation. Metabolism to dihydrodiols is 1 pathway in the activation of benzo(j)fluoranthene and benzo(k)fluoranthene to ultimate mutagens for S. typhimurium TA 100.