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National Institute of Environmental Health Sciences

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Publication Detail

Title: Mutagenicity of a glutathione conjugate of butadiene diepoxide.

Authors: Cho, Sung-Hee; Loecken, Elisabeth M; Guengerich, F Peter

Published In Chem Res Toxicol, (2010 Oct 18)

Abstract: The mutagenicity and carcinogenicity of the important commodity chemical 1,3-butadiene are attributed to the epoxide products. We confirmed our previous work showing that expression of rat glutathione (GSH) transferase 5-5 enhances the mutagenicity of butadiene diepoxide in Salmonella typhimurium TA1535. A GSH-butadiene diepoxide conjugate was isolated and fully characterized by mass spectrometry and nuclear magnetic resonance as S-(2-hydroxy-3,4-epoxybutyl)GSH. The conjugate had a t(½) of 2.6 h (pH 7.4, 37 °C) and was considerably more mutagenic than butadiene diepoxide or monoepoxide in S. typhimurium. We propose that the GSH conjugate may be a major species involved in butadiene genotoxicity, not a detoxication product.

PubMed ID: 20879737 Exiting the NIEHS site

MeSH Terms: Animals; Butadienes/chemistry*; DNA/metabolism; Epoxy Compounds/chemistry*; Epoxy Compounds/toxicity; Glutathione Transferase/metabolism; Glutathione/analogs & derivatives*; Glutathione/chemistry*; Glutathione/toxicity; Mutagenicity Tests; Rats; Salmonella typhimurium/drug effects; Salmonella typhimurium/metabolism

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