http://dx.doi.org/10.1016/j.chemosphere.2014.07.091">
 

Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Formation and characterization of glutathione adducts derived from polybrominated diphenyl ethers

Language

English

Abstract

© 2014 Elsevier Ltd. The reactions of glutathione (GSH) with polybrominated diphenyl ethers (PBDEs) quinones with different degrees of bromination on the PBDEs ring were studied. Liquid chromatography coupled with mass spectrometric (LC-MS) analysis showed that four types of adducts were formed from the reaction of each PBDEs quinone (PBDE-Q) with GSH. The proposed reaction pathway was confirmed using ion trap-MS/MS technique. Our results demonstrate that adduct-1 was formed following the Michael Addition, a reaction of the sulfhydryl group from GSH with electron deficient carbon from PBDEs-Q ring. Compared with other carbons on the quinone ring, carbon in position 6 has a smaller steric hindrance, thus the addition reaction is likely to occur in that position. Hydrated quinone-GSH adduct-1 is easily oxidized to generate an adduct-2 in an aqueous solution. Substitution reaction from bromine atom on adduct-2 quinone ring with sulfhydryl group from GSH further generates adduct-3 that is unstable and can be readily hydrolyzed to adduct-4 in aqueous solution. Both adduct-1 and adduct-4 were unstable as well, immediately oxidized to adduct-2 and adduct-3 in the air, respectively. The results reveal that brominated quinones undergo a rapid non-enzymatic debromination upon reaction with GSH, and open a new view for our understanding on mechanism of metabolism and the toxicity of this class of compounds.

Keywords

GSH, LC-MS, PBDE-quinone, PBDEs

Publication Date

2015

Source Publication Title

Chemosphere

Volume

120

Start Page

365

End Page

370

Publisher

Elsevier

ISSN (print)

00456535

ISSN (electronic)

18791298

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