Molecular Modeling Study of the Genotoxicity of the Sudan I and Sudan II Azo Dyes and Their Metabolites

Azo dyes are defined by the presence of a characteristic N=N group. Sudan I and Sudan II are synthetic azo dyes that have been used as coloring agents. Although animal toxicity studies suggest that Sudan dyes are mutagenic, their molecular mechanism of action is unknown, thus making it challenging t...

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Published inFrontiers in chemistry Vol. 10; p. 880782
Main Authors Bienstock, Rachelle J., Perera, Lalith, Pasquinelli, Melissa A.
Format Journal Article
LanguageEnglish
Published Frontiers Media S.A 23.06.2022
Subjects
azo dyes
Chemistry
DNA adducts
DNA damage
molecular dynamics simulations
Sudan I
Sudan II
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Summary:Azo dyes are defined by the presence of a characteristic N=N group. Sudan I and Sudan II are synthetic azo dyes that have been used as coloring agents. Although animal toxicity studies suggest that Sudan dyes are mutagenic, their molecular mechanism of action is unknown, thus making it challenging to establish thresholds for tolerable daily intake or to understand how these molecules could be modified to ameliorate toxicity. In addition, dye metabolites, such as azobiphenyl and 4-aminobiphenyl, have been correlated with epigenetic alterations. We shed some light on the mechanisms of Sudan dye genotoxicity through a molecular modeling study of Sudan I and Sudan II dyes and two common metabolites interacting with DNA as adducts. The results suggest that all four adducts cause significant perturbations to the DNA helical conformation and structure; thus, it can be inferred that DNA repair and replication processes would be significantly impacted.
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Edited by: Thomas S. Hofer, University of Innsbruck, Austria
Srinivasadesikan Venkatesan, Vignan’s Foundation for Science, Technology and Research, India
Reviewed by: José Pedro Cerón-Carrasco, Catholic University San Antonio of Murcia, Spain
This article was submitted to Theoretical and Computational Chemistry, a section of the journal Frontiers in Chemistry
ISSN:2296-2646
2296-2646
DOI:10.3389/fchem.2022.880782