Home
Resources
Publications
Genotoxicity of chryseno[4,5-bcd]thiophene and Its Sulfone Derivative

Genotoxicity of chryseno[4,5-bcd]thiophene and Its Sulfone Derivative

J E Sinsheimer, B H Hooberman, S K Das, P M Savla, A J Ashe 3rd

Environ Mol Mutagen. 1992;19(3):259-64.

PMID: 1572349

Abstract:

Our recent syntheses of chryseno[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. Our 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP551907643	Thiophene-4		551907-64-3	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: