The role of ethyl and fluorine substitution in the 4'-position for N,N-diethyl-4-aminoazobenzene mutagenicity and azo reduction.
The mutagenicity and azo reduction rate of N,N-diethyl-4-aminoazobenzene (DEAB) were influenced by substitution in the 4'-position with a ethyl or a fluorine group. The parent dye (DEAB) was shown to be slightly mutagenic with Salmonella typhimurium TA98 using Aroclor 1254-pretreated 9000 x g supernatant fractions from rat liver. Introduction of a 4'-ethyl group in DEAB did not affect mutagenicity of the dye, but a 4-fluoro group markedly enhanced its mutagenicity. DEAB underwent azo reduction and its reduction rate was influenced by 4'-substituents. A 4'-fluoro group in DEAB increased its azo reduction rate, while a 4'-ethyl group abolished it. Inhibitors of cytochrome P-450 also inhibited 4'-fluoro-DEAB mutagenicity and azo reduction.
D000818:Animals; D001391:Azo Compounds / Q000633:toxicity*; D004396:Coloring Agents / Q000378:metabolism / Q000633:toxicity*; D008099:Liver / Q000378:metabolism; D008297:Male; D009152:Mutagenicity Tests / Q000379:methods; D009153:Mutagens; D010084:Oxidation-Reduction; D051381:Rats; D013329:Structure-Activity Relationship; D010128:p-Aminoazobenzene / Q000031:analogs & derivatives / Q000378:metabolism / Q000633:toxicity*
D001391:Azo Compounds; D004396:Coloring Agents; D009153:Mutagens; C007368:C.I. Solvent Yellow 56; D010128:p-Aminoazobenzene