Sudan I, 1-Phenylazo-2-naphthol and Sudan II,  1-(2,4-Dimethylphenylazo)-2-naphthol are synthetic azo dyes which have been widely used as commericial and industrial coloring agents. Although Sudan dyes are considered mutagens (based on animal toxicity studies), their molecular mechanism of action is unknown. Additionally, azo dye metabolites and intermediates , such as azobiphenyl and 4-aminobiphenyl , have been correlated with epigenetic alterations. We will report computational modeling, molecular dynamics and MM/GBSA studies of Sudan dye-DNA adducts and dye metabolites-DNA interactions to gain an understaning of mechanisms of Sudan dye genotoxicity. Results presented suggest that all four DNA-adducts formed cause perturbation to the DNA helical conformation and structure, and significantly impact interactions with DNA repair and replication proteins.

Molecular modeling of genotoxic azo dyes, Sudan I and Sudan II, and their metabolites

2019 Fall National Meeting

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