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

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.

journal_name

Chemosphere

journal_title

Chemosphere

authors

Huang L,Li C,Lai Y,Qiu B,Cai Z

doi

10.1016/j.chemosphere.2014.04.108

subject

Has Abstract

pub_date

2015-01-01 00:00:00

pages

29-34

eissn

0045-6535

issn

1879-1298

pii

S0045-6535(14)00632-8

journal_volume

118

pub_type

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