Synthesis, Spectral Analysis, and Mutagenicity of 1-, 3-, and 6-Nitrobenzopyrene

Article abstract of DOI:10.1021/jm00375a012

The mutagenic environmental pollutants 1-, 3-, and 6-nitrobenzopyrene were synthesized.Nitration of 7,8,9,10-tetrahydrobenzopyrene with sodium nitrate in trifluoroacetic acid and acetic anhydride at ambient temperature gave a mixture of 1-, 3-, and 6-nitro-7,8,9,10-tetrahydrobenzopyrene, which was separated by chromatography.Dehydrogenation of the isolated nitrotetrahydrobenzopyrenes with 2,3-dichloro-4,5-dicyano-1,6-benzoquinone produced 1-, 3-, and 6-nitrobenzopyrene in high yield.Comparison of the spectral data of these compounds with those obtained from direct nitration of benzopyrene confirmed that 1- and 3-nitrobenzopyrenes are indeed the minor products of the latter reaction.This confirmation also verifies that 1- and 3-nitrobenzopyrene were the minor nitrated products of benzopyrene formed in model air atmospheres.The 1-, 3-, and 6-nitrobenzopyrene were mutagenic in Salmonella typhimurium tester strains TA98 and TA100 in the presence of a mammalian microsomal (S9) activating system.Both 1- and 3-nitrobenzopyrene, but not 6-nitrobenzopyrene, were also direct-acting mutagens in these strains.However, only 6-nitrobenzopyrene exhibited weak mutagenic activity when tested in Chinese hamster ovary cells, while only 3-nitrobenzopyrene produced a concentration-dependent decrease in cellular survival.