Relationships among direct-acting mutagenicity, nitro group orientation and polarographic reduction potential of 6-nitrobenzo[a]pyrene, 7-nitrobenz[a]anthracene and their derivatives.

The direct-acting mutagenicity in Salmonella typhimurium strains TA98 and TA100 and the half-wave reduction potentials of 6-nitrobenzo[a]pyrene (6-nitro-BaP), 7-nitrobenz[a]anthracene (7-nitro-BA), and a series of their derivatives were compared. The common structural feature of these compounds is that their nitro substituents, in order to minimize steric hindrance, preferentially adopt an orientation perpendicular or nearly perpendicular to the aromatic rings. All of the compounds, except 7-hydroxy-6-nitro-BaP and 7-acetoxy-6-nitro-BaP, were found to exhibit very weak or no direct-acting mutagenicity. 7-Acetoxy-6-nitro-BaP and 7-hydroxy-6-nitro-BaP were also found to have the lowest reduction potentials among the tested compounds. The results suggest that a combination of the orientation of the nitro substituent and the first half-wave reduction potential of the compound may correlate with the direct-acting bacterial mutagenicity of nitro-polycyclic aromatic hydrocarbons.