Fu P P, Heflich R H, Unruh L E, Shaikh A U, Wu Y S, Lai C C, Lai J S
National Center for Toxicological Research, Jefferson, AR 72079.
Mutat Res. 1988 Nov-Dec;209(3-4):115-22. doi: 10.1016/0165-7992(88)90027-9.
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.
比较了6-硝基苯并[a]芘（6-硝基-BaP）、7-硝基苯并[a]蒽（7-硝基-BA）及其一系列衍生物在鼠伤寒沙门氏菌TA98和TA100菌株中的直接致突变性以及它们的半波还原电位。这些化合物的共同结构特征是，为了使空间位阻最小化，它们的硝基取代基优先采取垂直或近乎垂直于芳环的取向。除7-羟基-6-硝基-BaP和7-乙酰氧基-6-硝基-BaP外，所有化合物均表现出非常弱的直接致突变性或无直接致突变性。7-乙酰氧基-6-硝基-BaP和7-羟基-6-硝基-BaP在测试化合物中也具有最低的还原电位。结果表明，硝基取代基的取向与化合物的第一个半波还原电位的组合可能与硝基多环芳烃的直接细菌致突变性相关。
