Literature DB >> 23416178

Mutagenicity of the cysteine S-conjugate sulfoxides of trichloroethylene and tetrachloroethylene in the Ames test.

Roy M Irving1, Adnan A Elfarra.   

Abstract

The nephrotoxicity and nephrocarcinogenicity of trichloroethylene (TCE) and tetrachloroethylene (PCE) are believed to be mediated primarily through the cysteine S-conjugate β-lyase-dependent bioactivation of the corresponding cysteine S-conjugate metabolites S-(1,2-dichlorovinyl)-l-cysteine (DCVC) and S-(1,2,2-trichlorovinyl)-l-cysteine (TCVC), respectively. DCVC and TCVC have previously been demonstrated to be mutagenic by the Ames Salmonella mutagenicity assay, and reduction in mutagenicity was observed upon treatment with the β-lyase inhibitor aminooxyacetic acid (AOAA). Because DCVC and TCVC can also be bioactivated through sulfoxidation to yield the potent nephrotoxicants S-(1,2-dichlorovinyl)-l-cysteine sulfoxide (DCVCS) and S-(1,2,2-trichlorovinyl)-l-cysteine sulfoxide (TCVCS), respectively, the mutagenic potential of these two sulfoxides was investigated using the Ames Salmonella typhimurium TA100 mutagenicity assay. The results show both DCVCS and TCVCS were mutagenic, and TCVCS exhibited 3-fold higher mutagenicity than DCVCS. However, DCVCS and TCVCS mutagenic activity was approximately 700-fold and 30-fold lower than DCVC and TCVC, respectively. DCVC and DCVCS appeared to induce toxicity in TA100, as evidenced by increased microcolony formation and decreased mutant frequency above threshold concentrations. TCVC and TCVCS were not toxic in TA100. The toxic effects of DCVC limited the sensitivity of TA100 to DCVC mutagenic effects and rendered it difficult to investigate the effects of AOAA on DCVC mutagenic activity. Collectively, these results suggest that DCVCS and TCVCS exerted a definite but weak mutagenicity in the TA100 strain. Therefore, despite their potent nephrotoxicity, DCVCS and TCVCS are not likely to play a major role in DCVC or TCVC mutagenicity in this strain.
Copyright © 2013 Elsevier Ireland Ltd. All rights reserved.

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Year:  2013        PMID: 23416178      PMCID: PMC3631458          DOI: 10.1016/j.tox.2013.02.003

Source DB:  PubMed          Journal:  Toxicology        ISSN: 0300-483X            Impact factor:   4.221


  34 in total

1.  Elevated urinary levels of kidney injury molecule-1 among Chinese factory workers exposed to trichloroethylene.

Authors:  Roel Vermeulen; Luoping Zhang; Annejet Spierenburg; Xiaojian Tang; Joseph V Bonventre; Boris Reiss; Min Shen; Martyn T Smith; Chuangyi Qiu; Yichen Ge; Zhiying Ji; Jun Xiong; Jian He; Zhenyue Hao; Songwang Liu; Yuxuan Xie; Fei Yue; Weihong Guo; Mark Purdue; Laura E Beane Freeman; Venkata Sabbisetti; Laiyu Li; Hanlin Huang; Nathaniel Rothman; Qing Lan
Journal:  Carcinogenesis       Date:  2012-06-04       Impact factor: 4.944

2.  Pathological excretion patterns of urinary proteins in renal cell cancer patients exposed to trichloroethylene.

Authors:  T Brüning; H Mann; H Melzer; A G Sundberg; H M Bolt
Journal:  Occup Med (Lond)       Date:  1999-07       Impact factor: 1.611

3.  Dose-dependent protein adduct formation in kidney, liver, and blood of rats and in human blood after perchloroethene inhalation.

Authors:  A Pähler; J Parker; W Dekant
Journal:  Toxicol Sci       Date:  1999-03       Impact factor: 4.849

4.  NTP 12th Report on Carcinogens.

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Journal:  Rep Carcinog       Date:  2011

5.  Globin monoadducts and cross-links provide evidence for the presence of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide, chlorothioketene, and 2-chlorothionoacetyl chloride in the circulation in rats administered S-(1,2-dichlorovinyl)-L-cysteine.

Authors:  Nella Barshteyn; Adnan A Elfarra
Journal:  Chem Res Toxicol       Date:  2009-09       Impact factor: 3.739

6.  Formation of three N-acetyl-L-cysteine monoadducts and one diadduct by the reaction of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide with N-acetyl-L-cysteine at physiological conditions: chemical mechanisms and toxicological implications.

Authors:  Nella Barshteyn; Adnan A Elfarra
Journal:  Chem Res Toxicol       Date:  2007-09-25       Impact factor: 3.739

7.  Reactivity of cysteine S-conjugate sulfoxides: formation of S-[1-chloro-2-(S-glutathionyl)vinyl]-L-cysteine sulfoxide by the reaction of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide with glutathione.

Authors:  P J Sausen; A A Elfarra
Journal:  Chem Res Toxicol       Date:  1991 Nov-Dec       Impact factor: 3.739

8.  Biotransformation of perchloroethene: dose-dependent excretion of trichloroacetic acid, dichloroacetic acid, and N-acetyl-S-(trichlorovinyl)-L-cysteine in rats and humans after inhalation.

Authors:  W Völkel; M Friedewald; E Lederer; A Pähler; J Parker; W Dekant
Journal:  Toxicol Appl Pharmacol       Date:  1998-11       Impact factor: 4.219

9.  Genotoxicity of crotonaldehyde in the bone marrow and germ cells of laboratory mice.

Authors:  Anand M Jha; Akhilesh C Singh; Uma Sinha; Mithilesh Kumar
Journal:  Mutat Res       Date:  2007-04-20       Impact factor: 2.433

10.  S-(1,2,2-trichlorovinyl)-L-cysteine sulfoxide, a reactive metabolite of S-(1,2,2-Trichlorovinyl)-L-cysteine formed in rat liver and kidney microsomes, is a potent nephrotoxicant.

Authors:  Adnan A Elfarra; Renee J Krause
Journal:  J Pharmacol Exp Ther       Date:  2007-03-08       Impact factor: 4.030

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  6 in total

1.  Impact of Nonalcoholic Fatty Liver Disease on Toxicokinetics of Tetrachloroethylene in Mice.

Authors:  Joseph A Cichocki; Shinji Furuya; Kranti Konganti; Yu-Syuan Luo; Thomas J McDonald; Yasuhiro Iwata; Weihsueh A Chiu; David W Threadgill; Igor P Pogribny; Ivan Rusyn
Journal:  J Pharmacol Exp Ther       Date:  2017-02-01       Impact factor: 4.030

2.  Simultaneous detection of the tetrachloroethylene metabolites S-(1,2,2-trichlorovinyl) glutathione, S-(1,2,2-trichlorovinyl)-L-cysteine, and N-acetyl-S-(1,2,2-trichlorovinyl)-L-cysteine in multiple mouse tissues via ultra-high performance liquid chromatography electrospray ionization tandem mass spectrometry.

Authors:  Yu-Syuan Luo; Joseph A Cichocki; Thomas J McDonald; Ivan Rusyn
Journal:  J Toxicol Environ Health A       Date:  2017-07-11

Review 3.  Trichloroethylene biotransformation and its role in mutagenicity, carcinogenicity and target organ toxicity.

Authors:  Lawrence H Lash; Weihsueh A Chiu; Kathryn Z Guyton; Ivan Rusyn
Journal:  Mutat Res Rev Mutat Res       Date:  2014 Oct-Dec       Impact factor: 5.657

4.  Characterization of inter-tissue and inter-strain variability of TCE glutathione conjugation metabolites DCVG, DCVC, and NAcDCVC in the mouse.

Authors:  Yu-Syuan Luo; Shinji Furuya; Weihsueh Chiu; Ivan Rusyn
Journal:  J Toxicol Environ Health A       Date:  2017-11-30

5.  Editor's Highlight: High-Throughput Functional Genomics Identifies Modulators of TCE Metabolite Genotoxicity and Candidate Susceptibility Genes.

Authors:  Vanessa Y De La Rosa; Jonathan Asfaha; Michael Fasullo; Alex Loguinov; Peng Li; Lee E Moore; Nathaniel Rothman; Jun Nakamura; James A Swenberg; Ghislaine Scelo; Luoping Zhang; Martyn T Smith; Chris D Vulpe
Journal:  Toxicol Sci       Date:  2017-11-01       Impact factor: 4.849

Review 6.  Trichloroethylene: Mechanistic, epidemiologic and other supporting evidence of carcinogenic hazard.

Authors:  Ivan Rusyn; Weihsueh A Chiu; Lawrence H Lash; Hans Kromhout; Johnni Hansen; Kathryn Z Guyton
Journal:  Pharmacol Ther       Date:  2013-08-23       Impact factor: 12.310

  6 in total

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