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author:

Huang, Lihua (Huang, Lihua.) [1] | Li, Charlie (Li, Charlie.) [2] | Lai, Yongquan (Lai, Yongquan.) [3] | Qiu, Bin (Qiu, Bin.) [4] | Cai, Zongwei (Cai, Zongwei.) [5]

Indexed by:

EI

Abstract:

Polybrominated diphenyl ethers (PBDEs) may be metabolized to form hydroxylated and quinone products. Study on the formation of DNA adducts altered by PBDEs quinones was conducted. Various types of DNA adducts generated from in vitro reaction of deoxyguanosine (dG), 2'-deoxyadenosine (dA), 2'-deoxycytidine (dC), thymidine (T) and DNA with a PBDE-quinone metabolite, namely 2-(2',4'-bromophenoxyl)-benzoquinone (2'4'BrPhO-BQ) were characterized. The results suggest that the quinone compound could form various DNA adducts with dG, dA and dC via Michael Addition, which was confirmed from analyses by electrospray ionization tandem mass spectrometry. Two adducts were respectively generated from the reactions of 2'4'BrPhO-BQ with dC and dG, while three adducts were produced with dA. The formation of adducts of 2'4'BrPhO-BQ-deoxynucleoside changed with different pH of reaction solution. The obtained results demonstrated that 2'4'BrPhO-BQ could covalently bind to DNA mediated by quinone group. The in vitro data of the formation of DNA adducts might be valuable to elucidate the mechanism of interaction between PBDEs and DNA in vivo. © 2014 Elsevier Ltd.

Keyword:

Addition reactions DNA Electrospray ionization Mass spectrometry Metabolites Organic pollutants Quinone

Community:

  • [ 1 ] [Huang, Lihua]Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety, Fuzhou University, Fuzhou; 350002, China
  • [ 2 ] [Huang, Lihua]State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong
  • [ 3 ] [Li, Charlie]California Department of Public Health, 850 Marina Bay Parkway, G365, Richmond; CA; 94564, United States
  • [ 4 ] [Lai, Yongquan]State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong
  • [ 5 ] [Qiu, Bin]Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety, Fuzhou University, Fuzhou; 350002, China
  • [ 6 ] [Qiu, Bin]State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong
  • [ 7 ] [Cai, Zongwei]State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong

Reprint 's Address:

  • [cai, zongwei]state key laboratory of environmental and biological analysis, department of chemistry, hong kong baptist university, kowloon tong, hong kong

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Source :

Chemosphere

ISSN: 0045-6535

Year: 2015

Issue: 1

Volume: 118

Page: 29-34

3 . 6 9 8

JCR@2015

8 . 1 0 0

JCR@2023

ESI HC Threshold:301

JCR Journal Grade:1

CAS Journal Grade:2

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count:

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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