STRUCTURAL BASIS OF THE MUTAGENICITY OF 1-AMINO-2-NAPHTHOL-BASED AZO DYES

A structure - activity study of 1-amino-2-naphthol derived azo dyes using CASE, the Computer Automated Structure Evaluation system, revealed that for optimal mutagenicity, reduction of the azo bond was required, thus suggesting that activity could be related to the liberated aromatic amines. Although it has long been known that sulfonation of azo dyes resulted in decreased carcinogenicity and mutagenicity, the present study elucidates the sites of sulfonation which will decrease mutagenicity maximally. Comparison of CASE predictions with available mutagenicity data indicates a concordance. Unexpectedly, CASE indicates that one of the aromatic amines obtained upon azoreduction of FD and C Red no. 40 is predicted to be mutagenic. © 1990 Oxford University Press.