TY - JOUR
T1 - DNA and RNA Adducts Formation from 3,4-Quinone Metabolites of Bisphenol F
AU - Wang, Xiaoxiao
AU - Cao, Guodong
AU - Yang, Zhiyi
AU - Zhao, Hongzhi
AU - Cai, Zongwei
N1 - The work was financially supported by the National Key Research and Development Program of China (2019YFC1804602 and 2017YFC1600500) and National Natural Science Foundation of China (21505111). The authors also thank Dr. Simon Wang at the Language Centre of HKBU for his help to improve the linguistic presentation.
Publisher Copyright:
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PY - 2021/11/9
Y1 - 2021/11/9
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85117512521&partnerID=8YFLogxK
U2 - 10.1021/acs.estlett.1c00753
DO - 10.1021/acs.estlett.1c00753
M3 - Journal article
AN - SCOPUS:85117512521
SN - 2328-8930
VL - 8
SP - 1009
EP - 1014
JO - Environmental Science and Technology Letters
JF - Environmental Science and Technology Letters
IS - 11
ER -
