Genotoxicity of chryseno[4,5-bcd]thiophene and its sulfone derivative
- Univ. of Michigan, Ann Arbor, MI (United States)
The authors' recent syntheses of cryseno[4,5-bcd]thiophene together with its potential sulfone metabolite, chryseno[4,5-bcd]thiophene-4,4-dioxide, have made these compounds available for genotoxicity testing. Such toxicity testing is of interest as this thiophene is an isoster of the established carcinogen benzo[a]pyrene and is one of the thiaarenes which are potential environmental contaminants found in fossil fuels. Although the thiophene was less mutagenic than benzo[a]pyrene in Salmonella strains TA98 and TA100 after S9 activation, it exhibited in vivo chromosomal aberration activity equal to that of benzo[a]pyrene in the bone-marrow cells of mice. A reduced activity with Salmonella as well as in the bone-marrow cell assay for the sulfone does not support its role as the key active metabolic intermediate for the genotoxicity of the thiophene. Molecular orbital calculations would be consistent with the concept of activation through a diol-epoxide mechanism and offers an explanation for the reduced genotoxicity of the sulfone via this mechanism. These genotoxicity studies support the concern that sulfur isosters of established carcinogenic polycyclic aromatic hydrocarbons could themselves be toxic. 21 refs., 2 figs., 3 tabs.
- OSTI ID:
- 6566273
- Journal Information:
- Environmental and Molecular Mutagenesis; (United States), Vol. 19:3; ISSN 0893-6692
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
CHRYSENE
GENETIC EFFECTS
POLYCYCLIC SULFUR HETEROCYCLES
BIOLOGICAL PATHWAYS
AROMATICS
BIOLOGICAL EFFECTS
CONDENSED AROMATICS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
560300* - Chemicals Metabolism & Toxicology