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Toxicological Sciences 56, 351-356 (2000)
Copyright © 2000 by the Society of Toxicology

Mutagenicity Studies of Benzidine and Its Analogs: Structure-Activity Relationships

King-Thom Chung*,1, Ssu-Ching Chen*, Tit Yee Wong*, Ying-Sing Li{dagger}, Cheng-I Wei{ddagger} and Ming W. Chou§

* Department of Microbiology and Molecular Cell Sciences, The University of Memphis, Memphis, Tennessee 38152; {dagger} Department of Chemistry, The University of Memphis, Memphis, Tennessee 38152; {ddagger} Department of Nutrition and Food Science, Auburn University, Auburn, Alabama 36849; and § National Center for Toxicology Research, Jefferson, Arkansas 72079

The Ames Salmonella/microsome assay was employed to test the mutagenicity of benzidine and its analogs using strains TA98 and TA100 in the presence and absence of Aroclor 1254-induced rat S9 mix. 3,3'-Dichlorobenzidine-2HCl and 4,4'-dinitro-2-biphenylamine were directly mutagenic to TA98, while 4,4'-dinitro-2-biphenylamine was directly mutagenic to both TA98 and TA100 in the absence of S9 mix. 2-Aminobiphenyl, 3-aminobiphenyl, and 3,3'-5,5'-tetramethylbenzidine were not mutagenic in either strains in the presence or absence of S9. In the presence of S9 mix, 4-aminobiphenyl, benzidine, 3,3'-dichlorobenzidine-2HCl, 3,3'-dimethoxybenzidine, 3,3'-4,4'-tetraaminobiphenyl, o-tolidine, N, N-N', N'-tetramethylbenzidine, and 4,4'-dinitro-2-biphenylamine were mutagenic to TA98; 4-aminobiphenyl, 3,3'-dichlorobenzidine-2HCl, 3,3'-dimethoxybenzidine, and 4,4'-dinitro-2-biphenylamine were mutagenic to TA100. Physicochemical parameters of these compounds including oxidation potentials, the energy difference between the lowest unoccupied molecular orbital and the highest occupied molecular orbital, ionization potentials, dipole moment, relative partition coefficient, and basicity did not correlate with their bacterial mutagenic activities.

Key Words: mutagenicity; oxidation potential; physicochemical properties.


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