title: Interaction of bisphenol A 3,4-quinone metabolite with glutathione and ribonucleosides/deoxyribonucleosides in vitro.
abstract: Bisphenol A is a monomer used in the manufacture of polycarbonate plastic products, epoxy resin-based food can liners and flame retardants. To determine the genotoxic potential of bisphenol A, the mechanism of the reactions between the reactive electophilic bisphenol A 3,4-quinone (BPAQ) with glutathione and ribonucleosides/deoxyribonucleosides were studied. The obtained results demonstrated that BPAQ reacted with 2'-deoxyguanosine (dG)/guanosine (G), 2'-deoxyadenosine (dA)/adenosine (A), but not with 2'-deoxycytidine (dC)/cytidine (C) and thymidine (T)/uridine (U) in aqueous acetic acid. The reactions were accompanied by loss of deoxyribose, and the rate of depurination by deoxyribonucleoside adducts were faster than that of ribonucleoside adducts. In mixtures of ribonucleosides and deoxyribonucleosides treated with BPAQ, reactions occurred more readily with dG/G than dA/A. The structures of the modified bases were confirmed by electrospray ionization tandem mass spectrometry (ESI-MS/MS). We also found that BPAQ reacted readily with glutathione (GSH) in aqueous acetic acid, and characterized the BPAQ-GSH conjugate by ESI-MS/MS. The in vitro data of depurinating DNA/RNA adducts and BPAQ-GSH adducts may provide appropriate reference for the identification of BPAQ adducts in environmental and biological systems.
authors.affiliation: State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Wu
authors.affiliation: State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Fang
authors.affiliation: State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China.
authors.forename: Shangfu
authors.initials: S
authors.lastname: Li
authors.affiliation: State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China.
authors.forename: Juntong
authors.initials: J
authors.lastname: Wei
authors.affiliation: State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China.
authors.forename: Zhiyi
authors.initials: Z
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China.
authors.forename: Hongzhi
authors.initials: H
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China.
authors.forename: Chao
authors.initials: C
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China; School of Environmental Science and Engineering, Guangdong University of Technology, Guangzhou, China. Electronic address: zwcai@hkbu.edu.hk.
authors.forename: Zongwei
authors.initials: Z
authors.lastname: Cai
mesh_terms: D001559:Benzhydryl Compounds / Q000737:chemistry* / Q000378:metabolism; D016227:Benzoquinones / Q000737:chemistry* / Q000378:metabolism; D001665:Binding Sites; D018736:DNA Adducts / Q000737:chemistry* / Q000378:metabolism; D003853:Deoxyribonucleosides / Q000737:chemistry* / Q000378:metabolism; D004785:Environmental Pollutants / Q000737:chemistry* / Q000378:metabolism; D005978:Glutathione / Q000737:chemistry* / Q000378:metabolism; D010636:Phenols / Q000737:chemistry* / Q000378:metabolism; D012263:Ribonucleosides / Q000737:chemistry* / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D016227:Benzoquinones; D018736:DNA Adducts; D003853:Deoxyribonucleosides; D004785:Environmental Pollutants; D005978:Glutathione; D010636:Phenols; D012263:Ribonucleosides; C487806:bisphenol A 3,4-quinone; D000098826:Bisphenol A Compounds
keywords: Bisphenol A; Bisphenol A 3,4-quinone; Deoxyribonucleoside; Glutathione; Ribonucleoside