Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Interaction of 2-(2′,4′-bromophenoxyl)-benzoquinone with deoxynucleosides and DNA in vitro

Language

English

Abstract

© 2014 Elsevier Ltd. 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.

Keywords

2-(2', 4'-bromophenoxyl)-benzoquinone, Deoxynucleosides, DNA, LC-MS, PBDEs

Publication Date

2015

Source Publication Title

Chemosphere

Volume

118

Start Page

29

End Page

34

Publisher

Elsevier

DOI

10.1016/j.chemosphere.2014.04.108

Link to Publisher's Edition

http://dx.doi.org/10.1016/j.chemosphere.2014.04.108

ISSN (print)

00456535

ISSN (electronic)

18791298

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