http://dx.doi.org/10.1021/es203068f">
 

Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

New evidence for toxicity of polybrominated diphenyl ethers: DNA adduct formation from quinone metabolites

Language

English

Abstract

This study investigated the formation of DNA adducts of polybrominated diphenyl ethers (PBDEs) and the possible mechanisms. DNA adduction was conducted by in vitro reaction of deoxyguanosine (dG) and DNA with PBDE-quinone (PBDE-Q) metabolites, and DNA adducts were characterized by using electrospray ionization tandem mass spectrometry. The results suggested DNA adduction involved Michael Addition between the exocyclic NH2 group at the N-2 position of dG and the electron-deficient carbon of quinone, followed by reductive cyclization with loss of (bromo-)1-hydroperoxy-benzene or water to form a type I or type II adduct. PBDE-Q with substituted bromine on the quinone ring was proven to be a favorable structure to form a type I adduct, while the absence of bromine on the quinone ring resulted in a type II adduct. Lower reactivity of adduction was also observed with increasing the number of bromine atoms on the phenoxyl ring. Our data clearly demonstrated PBDEs could covalently bind to DNA mediated by quinone metabolites, depending on the degree of bromine substitution. This study opened a new view on the mechanism of toxicity of PBDEs and reported the structure of PBDE-DNA adducts, which might be valuable for the evaluation on potential in vivo formation of PBDE-DNA adducts. © 2011 American Chemical Society.

Publication Date

2011

Source Publication Title

Environmental Science and Technology

Volume

45

Issue

24

Start Page

10720

End Page

10727

Publisher

American Chemical Society

ISSN (print)

0013936X

ISSN (electronic)

15205851

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