||Synthesis and Biological Activity of Cyclopenta Epoxides of PAH (Polycyclic Aromatic Hydrocarbons) Containing Peripherally Fused Cyclopenta Rings.
Bartczak, A. W. ;
Sangaiah, R. ;
Ball, L. M. ;
Gold, A. ;
||North Carolina Univ. at Chapel Hill. School of Public Health.;Health Effects Research Lab., Research Triangle Park, NC.;American Cancer Society, Inc., New York.
Aromatic polycyclic hydrocarbons ;
Hazardous materials ;
Toxic substances ;
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Polycyclic aromatic hydrocarbons (PAH) containing peripherally fused cyclopenta rings have been identified in soots from many different combustion sources. Metabolism and mutagenicity studies have been reported on the series of four cyclopenta-fused isomers derived from benzanthracene. On the basis of metabolite profiles and S9 concentration dependence of bacterial mutagenicity, it has been suggested that Aroclor 1254-induced rat liver S9 activates benz(e)aceanthrylene, benz(j)aceanthrylene, and benz(l)aceanthrylene predominantly via epoxidation of the cyclopenta ring, while other routes must be involved in the case of benz(k)acephenanthrylene. To test these conclusions, the cyclopenta epoxides of all four isomers of the cyclopenta benzanthracene derivatives have been synthesized and their biological activity evaluated in the Ames assay.