title: CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III.
abstract: This work describes the mutagenic response of Sudan III, an adulterant food dye, using Salmonella typhimurium assay and the generation of hazardous aromatic amines after different oxidation methods of this azo dye. For that, we used metabolic activation by S9, catalytic oxidation by ironporphyrin and electrochemistry oxidation in order to simulate endogenous oxidation conditions. The oxidation reactions promoted discoloration from 65% to 95% of Sudan III at 1 × 10(-4)molL(-1) and generation of 7.6 × 10(-7)molL(-1) to 0.31 × 10(-4)molL(-1) of aniline, o-anisidine, 2-methoxi-5-methylaniline, 4-aminobiphenyl, 4,4'-oxydianiline; 4,4'-diaminodiphenylmethane and 2,6-dimethylaniline. The results were confirmed by LC-MS-MS experiments. We also correlate the mutagenic effects of Sudan III using S. typhimurium with the strain TA1535 in the presence of exogenous metabolic activation (S9) with the metabolization products of this compound. Our findings clearly indicate that aromatic amines are formed due to oxidative reactions that can be promoted by hepatic cells, after the ingestion of Sudan III. Considering that, the use of azo compounds as food dyestuffs should be carefully controlled.
authors.affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Departamento de Análises Clínicas, Toxicológicas e Bromatológicas, Universidade de São Paulo, Avenida do Café, s/n, 14040-903 Ribeirão Preto, SP, Brazil.
authors.forename: Thalita Boldrin
authors.initials: TB
authors.lastname: Zanoni
authors.forename: Thiago M
authors.initials: TM
authors.lastname: Lizier
authors.forename: Marilda das Dores
authors.initials: Md
authors.lastname: Assis
authors.forename: Maria Valnice B
authors.initials: MV
authors.lastname: Zanoni
authors.forename: Danielle Palma
authors.initials: DP
authors.lastname: de Oliveira
mesh_terms: D000588:Amines / Q000032:analysis / Q000378:metabolism* / Q000633:toxicity; D000818:Animals; D001391:Azo Compounds / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity*; D002384:Catalysis; D004396:Coloring Agents / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D055664:Electrochemical Techniques; D005505:Food Coloring Agents / Q000633:toxicity; D007527:Isoenzymes / Q000378:metabolism; D008099:Liver / Q000201:enzymology; D008665:Metalloporphyrins / Q000737:chemistry / Q000378:metabolism; D009152:Mutagenicity Tests / Q000379:methods; D009154:Mutation; D010084:Oxidation-Reduction; D051381:Rats; D017207:Rats, Sprague-Dawley; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D053719:Tandem Mass Spectrometry
chemical_list: C492721:5,10,15,20-tetrakis(N-methyl-4'-pyridyl)porphyrinato-iron(III); D000588:Amines; D001391:Azo Compounds; D004396:Coloring Agents; D005505:Food Coloring Agents; D007527:Isoenzymes; D008665:Metalloporphyrins; D003577:Cytochrome P-450 Enzyme System; C033006:sudan III