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Genotoxicity of a Variety of Azobenzene and Aminoazobenzene Compounds in the Hepatocyte/DNA Repair Test and the Salmonella/Mutagenicity Test

Department of Pathology, Gifu University School of Medicine, 40 Tsukasa-machi, Gifu 500, Japan [H. M., S. S., N. Y., M. T.]; Laboratory of Radiochemistry, Gifu Pharmaceutical University, 6-1, Mitaborahigashi, Gifu 502, Japan [Y. M., H. N., H. Y., K. T.]; and Naylor Dana Institute, American Health Foundation, Valhalla, New York 10595 [G. M. W.]

Genotoxicity of 39 azo dye compounds of azobenzenes, aminoazobenzenes, and diaminoazobenzenes was examined in the hepatocyte primary culture/DNA repair test. Azobenzene (AzB) and 3,3'- or 4,4'-substituted azobenzenes such as (CH₃)₂AzB, (CH₂OH)₂AzB, (CH₂OCOCH₃)₂AzB, and (CH₂Cl)₂AzB did not generate DNA repair, indicating lack of genotoxicity of these compounds. In contrast, all of 24 aminoazobenzenes, including those of unknown carcinogenicity, i.e., 3'-methyl-4-aminoazobenzene, 3'-CH₂OH-aminoazobenzene, 3'-hydroxymethyl-N-methyl-4-aminoazobenzene, 3'-COOH-methylaminoazobenzene, 4'-formyl-N,,N-dimethyl-4-aminoazobenzene, 3'-CH₂Cl-dimethylaminoazobenzene, 4'-CH₂Cl-dimethylaminoazobenzene, and 2'-, 3'-, or 4'-CH₂OCOCH₃-dimethylaminoazobenzene, elicited DNA repair synthesis. A positive DNA repair response was obtained for the 3 of 6 tested diaminoazobenzenes, i.e., N'-acetyl-N'-methyl-4-amino-dimethylaminoazobenzene, N'-acetyl-N'-methyl-4-amino-methylaminoazobenzene, and N'-acetyl-N'-methyl-4-amino-N-acetyl-methylaminoazobenzene, which are known to be carcinogenic. These results indicate that the amino group is functional for the expression of genotoxicity of azobenzene compounds. Twenty-one azobenzenes of these 3 classes were also examined for their mutagenicity in the Salmonella/mutagenicity assay. These results were almost identical with those of the DNA repair test except for several azo dyes such as AzB and 4,4'-(CH₂Oacetyl)₂AzB of the azobenzenes and N'-acetyl-4-amino-dimethylaminoazobenzene and N'-acetyl-N-methyl-4-amino-N-acetyl methylaminoazobenzene of the diaminoazobenzenes.

¹ To whom requests for reprints should be addressed.

Received 5/17/85. Revised 9/18/85. Revised 12/11/85. Accepted 12/26/85.