NITRO-GROUP ORIENTATION, REDUCTION POTENTIAL, AND DIRECT-ACTING MUTAGENICITY OF NITRO-POLYCYCLIC AROMATIC-HYDROCARBONS
NITRO-GROUP ORIENTATION, REDUCTION POTENTIAL, AND DIRECT-ACTING MUTAGENICITY OF NITRO-POLYCYCLIC AROMATIC-HYDROCARBONS
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DOI：
10.1002/em.2850170306
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发表时间：
1991-01-01
影响因子：
2.8
通讯作者：
FU, PP
中科院分区：
文献类型：
--
作者：
JUNG, HW;SHAIKH, AU;FU, PP
硝基多环芳烃（nitro-polycyclic aromatic hydrocarbons，NPAHs）是一种广泛存在的具有遗传毒性的环境污染物。 我们一直有兴趣在确定的结构和电子功能，可能是有用的预测直接作用的诱变活性的硝基多环芳烃在鼠伤寒沙门氏菌。 在这项研究中，一系列结构相关的硝基多环芳烃被用来确定直接作用的致突变性，硝基的方向，硝基的还原电位之间的关系。这些化合物由同分异构的单硝化和二硝化苯并[e]芘、它们的衍生物和其他大小从2到5个芳香环分子的硝基多环芳烃组成。 一个普遍的发现是，硝基多环芳烃与其硝基取代基的取向垂直的芳香系统表现出非常弱或没有直接作用的诱变性在S。鼠伤寒菌株TA 98和TA 100。 然而，如果这种类型的硝基PAH具有相对低的第一半波还原电位，则其可能是直接作用的。 此外，只有当化合物结构相似时，才发现第一个半波还原电位和直接作用致突变性之间呈正相关。 因此，不能使用不同分子大小的硝基多环芳烃的相关性。 具有垂直硝基取向的硝基多环芳烃总是比具有平行取向的异构体具有更高的（绝对值）第一半波还原电位。 可能是由于第二个硝基吸电子，二硝基多环芳烃总是有一个较低的第一个半波还原电位比他们的一硝基类似物。 这些发现为解释和预测硝基多环芳烃的直接致突变性提供了有用的分子基础。
Nitro-polycyclic aromatic hydrocarbons (nitro-PAHs) are widespread genotoxic environmental pollutants. We have been interested in determining the structural and electronic features that may be useful in predicting the direct-acting mutagenic activity of nitro-PAHs in Salmonella typhimurium. In this study, a series of structurally related nitro-PAHs were used to determine the relationships among direct-acting mutagenicity, orientation of the nitro group, and reduction potential of the nitro group. The compounds consisted of isomeric mononitrated and dinitrated benzo[e]pyrenes, their derivatives,and other nitro-PAHs ranging from two to five aromatic-ring molecules in size. A general finding is that nitro-PAHs with their nitro substituent oriented perpendicular to the aromatic system exhibit either very weak or no direct-acting mutagenicity in S. typhimurium strains TA98 and TA100. However, if a nitro-PAH of this type has a relatively low first half-wave reduction potential, it may be direct-acting. Furthermore, a positive correlation between the first half-wave reduction potential and direct-acting mutagenicity is found only when the compounds are structurally similar. Consequently, the correlation cannot be made using nitro-PAHs with different molecular size. Nitro-PAHs having a perpendicular nitro orientation always have a higher (absolute value) first half-wave reduction potential than the isomer(s) with a parallel orientation. Perhaps due to electron-withdrawing by the second nitro group, dinitro-PAHs always have a lower first half-wave reduction potential than their mononitro analogues. These findings provide a useful molecular basis for interpreting and predicting the direct-acting mutagenicity of nitro-PAHs.