DNA and RNA Adducts Formation from 3,4-Quinone Metabolites of Bisphenol F

Bisphenol F (BPF) has been widely used as the predominant substitute of bisphenol A to increase the thickness and durability of industrial materials such as epoxy resins and coatings. In this study, formation of deoxyribonucleoside/ribonucleoside adducts from quinone metabolites of BPF was investigated by using ultrahigh performance liquid chromatography coupled with Orbitrap high-resolution mass spectrometry. The results suggested that both deoxyribonucleosides and ribonucleosides could covalently bind to the chemosynthetic and biotransformed BPF-quinone. The exocyclic NH2 group and the N-7 of deoxyguanosine (dG) and deoxyadenosine (dA) could nucleophilically react with the deficient carbon C-6 from BPF-quinone to form two types of adducts, whereas the Michael addition occurred between the amino groups from guanosine (G), adenosine (A), and deoxycytidine (dC), as well as cytidine (C) and carbon C-6 from quinone. No adducts were detected between BPF-quinone and thymine (T) and uracil (U) because the two carbonyl groups near the N-1 from T and U increased the steric hindrance of the addition reaction. The formation of DNA and RNA adducts of BPF through its metabolic activation may provide important information for the investigation of BPF genotoxicity.