Mutagenic activity of the 4,5- and 9,10-dihydrodiols of benzo[i]fluoranthene and their syn- and anti-dihydrodiol epoxides in Salmonella typhimurium
- Park One Research Labs., Sugar Land, TX (United States)
- Rutgers Univ., Piscataway, NJ (United States)
The objective of this study was to determine the relative mutagenic activities of the major dihydrodiol metabolites of benzo[i]fluoranthene (B[i]F) and their corresponding syn- and anti-dihydrodiol epoxides. Salmonella typhimurium tester strains TA97a, TA98, and TA100 were used to evaluate the mutagenic potencies of the parent hydrocarbon and these suspect proximate and ultimate mutagenic metabolites. B[i]F and the trans-dihydrodiol metabolites were active only in the presence of an external metabolic activation system (S9) with the exception of the B[i]F-4,5-diol, which was weakly active in TA98 and TA100 in the absence of S9. The B[i]F-4,5-diol was more mutagenic than the B[i]F-9,10-diol in tester strains TA98 and TA100, whereas the opposite effect was observed in TA97a. In the absence of S9, the anti-B[i]F-4,5-diol epoxide was more mutagenic than the syn-B[i]F-4,5-diol epoxide and the syn- and anti-B[i]F-9,10-diol epoxides in tester strains TA97a and TA100. The exceptional mutagenic potency of the anti-B[i]F-4,5-diol epoxide in TA100 resembles that observed by epoxides located within a fjord, or by the anti-diol epoxides of bay region methylated polycyclic aromatic hydrocarbons. In contrast, the mutagenicity of the pseudo bay region dihydrodiol epoxides arising from the B[i]F-9,10-diol more closely resembles that observed with the classical bay region dihydrodiol epoxides of chrysene. In summary, both dihydrodiol metabolites of B[i]F are mutagenic in S. typhimurium, and the relative potency varies among the tester strains. The highest mutagenic response was achieved in tester strain TA100, which detects base-pair substitutions. The most potent direct-acting dihydrodiol epoxide in this tester strain was the anti-B[i]F-4,5-diol epoxide, which agrees with the results of mouse skin painting studies that indicate that the B[i]F-4,5-diol is more tumorigenic than the parent hydrocarbon or the B[i]F-9,10-diol. 34 refs., 7 figs., 2 tabs.
- OSTI ID:
- 7074811
- Journal Information:
- Environmental and Molecular Mutagenesis; (United States), Vol. 22:1; ISSN 0893-6692
- Country of Publication:
- United States
- Language:
- English
Similar Records
Bisdihydrodiols, rather than dihydrodiol oxides, are the principal microsomal metabolites of tumorigenic trans-3,4-dihydroxy-3,4-dihydrodibenz[a,h]anthracene
Fluoranthene metabolism: Human and rat liver microsomes display different stereoselective formation of the trans-2,3-dihydrodiol
Related Subjects
59 BASIC BIOLOGICAL SCIENCES
CONDENSED AROMATICS
MUTAGENESIS
EPOXIDES
GLYCOLS
POLYCYCLIC AROMATIC HYDROCARBONS
STRUCTURE-ACTIVITY RELATIONSHIPS
ALCOHOLS
AROMATICS
HYDROCARBONS
HYDROXY COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
560300* - Chemicals Metabolism & Toxicology
550400 - Genetics