Structure-activity relationship studies on the mutagenicity of some azo dyes in the Salmonella/microsome assay.
Analogs of Direct Black 19 and Direct Black 38 were synthesized and tested in the Salmonella/microsome assay. Those dyes which gave positive responses in strains TA98 and TA1538 would be expected to be metabolized to p-phenylenediamine by the liver microsomal enzymes (S9). Pure p-phenylenediamine is non-mutagenic in this assay but becomes mutagenic after it is oxidized. Thus the positive response of our synthetic azo compounds are most likely due to the formation of oxidized p-phenylenediamine. Modification of the moieties that can be metabolized to p-phenylenediamine by sulfonation, carboxylation or copper complexation eliminated the mutagenic responses.
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J.C. Wilson Center for Technology, Xerox Corporation, Webster, NY 14580.
Solodar
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D000818:Animals; D001391:Azo Compounds / Q000378:metabolism / Q000494:pharmacology*; D001711:Biotransformation; D004396:Coloring Agents / Q000494:pharmacology*; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D009152:Mutagenicity Tests; D009153:Mutagens; D051381:Rats; D011919:Rats, Inbred Strains; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
D001391:Azo Compounds; D004396:Coloring Agents; D009153:Mutagens