Nitro polycyclic aromatic hydrocarbons mutagenicity

Jung, H., A. U. Shaikh, R. H. Heflich, and P. P. Fu, Nitro Group Orientation, Reduction Potential, and Direct-Acting Mutagenicity of Nitro-Polycyclic Aromatic Hydrocarbons, Environ. Mol. Mutagen., 17, 169-180 (1991). 

Yu, S., D. Herreno-Saenz, D. W. Miller, F. F. Kadlubar, and P. P. Fu, Mutagenicity of Nitro-Polycyclic Aromatic Hydrocarbons with the Nitro Substituent Situated at the Longest Molecular Axis, Mutat. Res., 283, 45-52 (1992). 

Wise, S. A., S. N. Chesler, L. R. Hilpert, W. E. May, R. E. Rebbert, C. R. Vogt, M. G. Nishioka, A. Austin, and J. Lewtas, Quantification of Polycyclic Aromatic Hydrocarbons and Nitro-Sub-stituted Polycyclic Aromatic Hydrocarbons and Mutagenicity Testing for the Characterization of Ambient Air Particulate Matter, Environ. Int., II, 147-160 (1985). 

P.P. Fu et al., The orientation of the nitro substituent predicts the direct-acting bacterial mutagenicity of nitrated polycyclic aromatic hydrocarbons. MutaL Res. 143, 173-181 (1985)... 

The soot from diesel engines and wood smoke carry mutagenic polycyclic aromatic hydrocarbons and their nitro derivatives.45 Some typical ones are shown in 15.1, the first being a potent mutagen in the Ames Salmonella test. Catalytic afterburners (containing platinum) are now required... 

W. L. Belser Jr., G. B. Knudson, and P. M. Hynds. 1978. Atmospheric reactions of polycyclic aromatic hydrocarbons Facile formation of mutagenic nitro derivatives. Science 202 515-519. 

On the other hand, direct acting mutagens such as nitro-substi-tuted polycyclic aromatic hydrocarbons have been detected in diesel exhaust emissions and may be responsible for a major portion of the mutagenic activity. However, in view of the presence of a variety of detoxification enzymes in human cells, the distinction between direct acting and activatable mutagens may not be justified for the assessment of health hazards. 

Song, X.-H., Xiao, M., and Yu, R.-Q. (1994) Artificial neural networks applied to classification of mutagenic activity of nitro-substituted polycyclic aromatic hydrocarbons. Comput. Chem. 18,391-396. 

Polycyclic aromatic hydrocarbons are ubiquitous in the atmosphere. Maximum concentrations often occur in urban areas, resulting primarily from engine exhaust and other forms of combustion. These processes produce compoimds that may be carried across continents and oceans, particularly in highly industrialized areas of the northern hemisphere (Simoneit and Mazurek, 1981). High molecular weight PAH, such as fluoranthene, pyrene, chrysene, benz[a]anthracene, benzofluoranthenes, benzo[a]pyrene, and benzo[e]pyrene are commonly encountered in urban atmospheres (Simoneit and Mazurek, 1981). Low molecular weight PAH are also widely distributed and include unsubstituted and alkyl naphathalene, phenanthrene, acenaphthene, and fluorene. PAH react in the upper atmosphere with NO to form nitro-derivatives, which are mutagenic. 

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