Effect of Alkoxy Substituents on the Mutagenicity of Some Phenylenediamine-Based Disazo Dyes

摘要

Fifteen aminoazobenzene dyes and seven of their reductive-cleavage products were examined in the Salmonella/microsome assay with strains TA98, TA100, TA1535, TA1537 and TA1538. Dyes tested included five derivatives of 4-aminoazobenzene with different alkoxy substituents (-OCH3, -OCH2CH3, -OCH2CH2CH3, -OCH2CH2CH2CH3 or -OCH2CH2OH) in the 3-position as well as the corresponding derivatives of 4-((4-aminophenyl)azo)N,N-diethylaniline and 4-((4-aminophenyl)azo)N,N-bis(2-hydroxyethyl)aniline. In general, as the size of the substituent ortho to the primary amino group of the dyes was increased, the mutagenicity decreased. A similar trend was observed for the reductive-cleavage products. The results from the latter aspect of the study suggest that the mutagenicity of aminoazobenzene dyes can not be accounted for solely from the properties of their reductive-cleavage products. (Copyright (c) 1990 Elsevier Science Publishers B.V. (Biomedical Division).)