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

Xiaoxiao Wang, Guodong Cao, Zhiyi Yang, Hongzhi Zhao*, Zongwei Cai*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

6 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)1009-1014
Number of pages6
JournalEnvironmental Science and Technology Letters
Issue number11
Early online date28 Sept 2021
Publication statusPublished - 9 Nov 2021

Scopus Subject Areas

  • Environmental Chemistry
  • Ecology
  • Water Science and Technology
  • Waste Management and Disposal
  • Pollution
  • Health, Toxicology and Mutagenesis


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