The nitrovinyl moiety determines the cyto- and genotoxic profiles of β-nitrostyrene derivatives: evidence from in silico and in vitro evaluation

cells demonstrated that the nitrovinyl moiety of β-nitrostyrene seems vital for its cytotoxic (membrane damage, metabolic competence) and genotoxic (clastogenicity, mutagenicity) properties. The extent of adversity varied with modification of structural elements. For example 1-nitro-2-[(E)-2-nitroethenyl]benzene led to 2.3-fold higher mean tail intensities in the alkaline comet assay than β-nitrostyrene. Notably, all derivatives with a nitrovinyl moiety, except 5-[(E)-2-nitroethenyl]-1,3-benzodioxole, induced DNA double-strand breaks, as judged by γH2A.X induction. In conclusion, our study identified structural elements responsible for the cyto- and genotoxic potential of β-nitrostyrene, demonstrating that minor structural changes can significantly alter its adverse biological activity.