Literature DB >> 20879737

Mutagenicity of a glutathione conjugate of butadiene diepoxide.

Sung-Hee Cho1, Elisabeth M Loecken, F Peter Guengerich.   

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.

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Year:  2010        PMID： 20879737      PMCID： PMC3848503          DOI： 10.1021/tx100304f

Source DB:  PubMed          Journal:  Chem Res Toxicol        ISSN： 0893-228X            Impact factor:   3.739


  23 in total

1.  Comparison of the DNA-alkylating properties and mutagenic responses of a series of S-(2-haloethyl)-substituted cysteine and glutathione derivatives.

Authors:  W G Humphreys; D H Kim; J L Cmarik; T Shimada; F P Guengerich
Journal:  Biochemistry       Date:  1990-11-13       Impact factor: 3.162

2.  Hepatic and pulmonary glutathione conjugation of 1,2:3,4-diepoxybutane in human, rat, and mouse in vitro.

Authors:  P J Boogaard; S C Sumner; M J Turner; J A Bond
Journal:  Toxicology       Date:  1996-10-28       Impact factor: 4.221

3.  Butadiene and isoprene: future studies and implications.

Authors:  H M Bolt
Journal:  Toxicology       Date:  1996-10-28       Impact factor: 4.221

Review 4.  Genotoxic properties of 1,3-butadiene.

Authors:  C de Meester
Journal:  Mutat Res       Date:  1988-05       Impact factor: 2.433

5.  Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione S-transferase.

Authors:  R Thier; M Müller; J B Taylor; S E Pemble; B Ketterer; F P Guengerich
Journal:  Chem Res Toxicol       Date:  1995 Apr-May       Impact factor: 3.739

6.  Characterization of N1- and N6-adenosine adducts and N1-inosine adducts formed by the reaction of butadiene monoxide with adenosine: evidence for the N1-adenosine adducts as major initial products.

Authors:  R R Selzer; A A Elfarra
Journal:  Chem Res Toxicol       Date:  1996 Jul-Aug       Impact factor: 3.739

7.  The reaction of 3,4-epoxy-1-butene with deoxyguanosine and DNA in vitro: synthesis and characterization of the main adducts.

Authors:  L Citti; P G Gervasi; G Turchi; G Bellucci; R Bianchini
Journal:  Carcinogenesis       Date:  1984-01       Impact factor: 4.944

8.  Mutagenicity of butadiene and its epoxide metabolites: I. Mutagenic potential of 1,2-epoxybutene, 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts.

Authors:  J E Cochrane; T R Skopek
Journal:  Carcinogenesis       Date:  1994-04       Impact factor: 4.944

9.  Human glutathione S-transferase T1-1 enhances mutagenicity of 1,2-dibromoethane, dibromomethane and 1,2,3,4-diepoxybutane in Salmonella typhimurium.

Authors:  R Thier; S E Pemble; H Kramer; J B Taylor; F P Guengerich; B Ketterer
Journal:  Carcinogenesis       Date:  1996-01       Impact factor: 4.944

10.  Glutathione conjugation of 1,2:3,4- diepoxybutane in human liver and rat and mouse liver and lung in vitro.

Authors:  P J Boogaard; S C Sumner; J A Bond
Journal:  Toxicol Appl Pharmacol       Date:  1996-02       Impact factor: 4.219
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  8 in total

1.  Conjugation of butadiene diepoxide with glutathione yields DNA adducts in vitro and in vivo.

Authors:  Sung-Hee Cho; F Peter Guengerich
Journal:  Chem Res Toxicol       Date:  2012-01-09       Impact factor: 3.739

2.  Mutation spectra of S-(2-hydroxy-3,4-epoxybutyl)glutathione: comparison with 1,3-butadiene and its metabolites in the Escherichia coli rpoB gene.

Authors:  Sung-Hee Cho; F Peter Guengerich
Journal:  Chem Res Toxicol       Date:  2012-06-15       Impact factor: 3.739

3.  In vivo roles of conjugation with glutathione and O6-alkylguanine DNA-alkyltransferase in the mutagenicity of the bis-electrophiles 1,2-dibromoethane and 1,2,3,4-diepoxybutane in mice.

Authors:  Sung-Hee Cho; F Peter Guengerich
Journal:  Chem Res Toxicol       Date:  2013-11-06       Impact factor: 3.739

4.  Replication past the butadiene diepoxide-derived DNA adduct S-[4-(N(6)-deoxyadenosinyl)-2,3-dihydroxybutyl]glutathione by DNA polymerases.

Authors:  Sung-Hee Cho; F Peter Guengerich
Journal:  Chem Res Toxicol       Date:  2013-06-04       Impact factor: 3.739

5.  Nrf2 Regulates the Sensitivity of Mouse Keratinocytes to Nitrogen Mustard via Multidrug Resistance-Associated Protein 1 (Mrp1).

Authors:  Ronald G Udasin; Xia Wen; Kristin M Bircsak; Lauren M Aleksunes; Michael P Shakarjian; Ah-Ng Tony Kong; Diane E Heck; Debra L Laskin; Jeffrey D Laskin
Journal:  Toxicol Sci       Date:  2015-10-09       Impact factor: 4.849

6.  Bis-butanediol-mercapturic acid (bis-BDMA) as a urinary biomarker of metabolic activation of butadiene to its ultimate carcinogenic species.

Authors:  Srikanth Kotapati; Dewakar Sangaraju; Amanda Esades; Lance Hallberg; Vernon E Walker; James A Swenberg; Natalia Y Tretyakova
Journal:  Carcinogenesis       Date:  2014-02-14       Impact factor: 4.944

7.  Interindividual Differences in DNA Adduct Formation and Detoxification of 1,3-Butadiene-Derived Epoxide in Human HapMap Cell Lines.

Authors:  Amanda Degner; Rashi Arora; Luke Erber; Christopher Chao; Lisa A Peterson; Natalia Y Tretyakova
Journal:  Chem Res Toxicol       Date:  2020-04-15       Impact factor: 3.739

Review 8.  On enzyme-based anticancer molecular dietary manipulations.

Authors:  Andrea Sapone; Donatella Canistro; Simone Melega; Ramona Moles; Fabio Vivarelli; Moreno Paolini
Journal:  J Biomed Biotechnol       Date:  2012-09-20
  8 in total

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