Bienstock Rachelle J, Perera Lalith, Pasquinelli Melissa A
Fiber and Polymer Science Program, Wilson College of Textiles, North Carolina State University, Raleigh, NC, United States.
National Institute of Environmental Health Sciences, Research Triangle Park, Durham, NC, United States.
Front Chem. 2022 Jun 23;10:880782. doi: 10.3389/fchem.2022.880782. eCollection 2022.
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.
偶氮染料是由特征性的N=N基团的存在来定义的。苏丹红I和苏丹红II是用作着色剂的合成偶氮染料。尽管动物毒性研究表明苏丹染料具有致突变性，但其分子作用机制尚不清楚，因此难以确定可耐受每日摄入量的阈值，也难以理解如何对这些分子进行修饰以减轻毒性。此外，染料代谢产物，如偶氮联苯和4-氨基联苯，已与表观遗传改变相关联。我们通过对苏丹红I和苏丹红II染料以及两种作为加合物与DNA相互作用的常见代谢产物进行分子建模研究，对苏丹染料的遗传毒性机制有了一些了解。结果表明，所有四种加合物都会对DNA螺旋构象和结构造成显著扰动；因此，可以推断DNA修复和复制过程将受到显著影响。
