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

References

• Bartels, M. J. 1994. Quantitation of the tetrachloroethylene metabolite N-acetyl-S-(trichlorovinyl)cysteine in rat urine via negative ion chemical ionization gas chromatography/tandem mass spectrometry. Biol. Mass Spectrom. 23:689–694.
   PubMedGoogle Scholar
• Birner, G., Bernauer, U., Werner, M., and Dekant, W. 1997. Biotransformation, excretion and nephrotoxicity of haloalkene-derived cysteine S-conjugates. Arch. Toxicol. 72:1–8.
   PubMed Web of Science ®Google Scholar
• Birner, G., Rutkowska, A., and Dekant, W. 1996. N-acetyl-S-(1,2,2-trichlorovinyl)-L-cysteine and 2,2,2-trichloroethanol: Two novel metabolites of tetrachloroethene in humans after occupational exposure. Drug Metab. Dispos. 24:41–48.
   PubMed Web of Science ®Google Scholar
• Bradford, B. U., Lock, E. F., Kosyk, O., Kim, S., Uehara, T., Harbourt, D., DeSimone, M., Threadgill, D. W., Tryndyak, V., Pogribny, I. P., Bleyle, L., Koop, D. R., and Rusyn, I. 2011. Interstrain differences in the liver effects of trichloroethylene in a multistrain panel of inbred mice. Toxicol. Sci. 120:206–217.
   PubMed Web of Science ®Google Scholar
• Buben, J. A. and O’Flaherty, E. J. 1985. Delineation of the role of metabolism in the hepatotoxicity of trichloroethylene and perchloroethylene: A dose-effect study. Toxicol. Appl. Pharmacol. 78:105–122.
   PubMed Web of Science ®Google Scholar
• Chiu, W. A. and Ginsberg, G. L. 2011. Development and evaluation of a harmonized physiologically based pharmacokinetic (PBPK) model for perchloroethylene toxicokinetics in mice, rats, and humans. Toxicol. Appl. Pharmacol. 253:203–234.
   PubMed Web of Science ®Google Scholar
• Cichocki, J. A., Guyton, K. Z., Guha, N., Chiu, W. A., Rusyn, I., and Lash, L. H. 2016. Target organ metabolism, toxicity, and mechanisms of trichloroethylene and perchloroethylene: Key similarities, differences, and data gaps. J. Pharmacol. Exp. Ther. 359:110–123.
   PubMed Web of Science ®Google Scholar
• Dekant, W. 1993. Bioactivation of nephrotoxins and renal carcinogens by glutathione S-conjugate formation. Toxicol. Lett. 67:151–160.
   PubMed Web of Science ®Google Scholar
• Dekant, W., Birner, G., Werner, M., and Parker, J. 1998. Glutathione conjugation of perchloroethene in subcellular fractions from rodent and human liver and kidney. Chem. Biol. Interact. 116:31–43.
   PubMed Web of Science ®Google Scholar
• Elfarra, A. A. and Krause, R. J. 2007. 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. J. Pharmacol. Exp. Ther. 32:1095–1101.
   Web of Science ®Google Scholar
• U.S. EPA 2011. “Toxicological Review of Tetrachloroethylene (CAS No. 127-18-4).” Support of Summary Information on the Integrated Risk Information System (IRIS). Washington, DC: U.S. Environmental Protection Agency.
   Google Scholar
• Griffith, O. W. and Meister, A. 1979. Glutathione: Interorgan translocation, turnover, and metabolism. Proc. Natl. Acad. Sci. U.S.A. 76:5606–5610.
   PubMed Web of Science ®Google Scholar
• Guyton, K. Z., Hogan, K. A., Scott, C. S., Cooper, G. S., Bale, A. S., Kopylev, L., Barone, S., Makris, S. L., Glenn, B., Subramaniam, R. P., Gwinn, M. R., Dzubow, R. C., and Chiu, W. A. 2014. Human health effects of tetrachloroethylene: Key findings and scientific issues. Environ. Health. Persp. 122:325–334.
   PubMed Web of Science ®Google Scholar
• Heuner, A., Dekant, W., Schwegler, J. S., and Silbernagl, S. 1991. Localization and capacity of the last step of mercapturic acid biosynthesis and the reabsorption and acetylation of cysteine S-conjugates in the rat kidney. Pflugers Arch. 417:523–527.
   PubMed Web of Science ®Google Scholar
• Hinchman, C. A., Matsumoto, H., Simmons, T. W., and Ballatori, N. 1991. Intrahepatic conversion of a glutathione conjugate to its mercapturic acid. Metabolism of 1-chloro-2,4-dinitrobenzene in isolated perfused rat and guinea pig livers. J. Biol. Chem. 266:22179–22185.
   PubMed Web of Science ®Google Scholar
• IARC. 2014. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans (Vol. 106). Trichloroethylene, Tetrachloroethylene and Some Other Chlorinated Agents. 106. Lyon, France.
   Google Scholar
• Irving, R. M. and Elfarra, A. A. 2013. Mutagenicity of the cysteine S-conjugate sulfoxides of trichloroethylene and tetrachloroethylene in the Ames test. Toxicology 306C:157–161.
   Web of Science ®Google Scholar
• Kim, S., Kim, D., Pollack, G. M., Collins, L. B., and Rusyn, I. 2009. Pharmacokinetic analysis of trichloroethylene metabolism in male B6C3F1 mice: formation and disposition of trichloroacetic acid, dichloroacetic acid, S-(1,2-dichlorovinyl)glutathione and S-(1,2-dichlorovinyl)-L-cysteine. Toxicol. Appl. Pharmacol. 238:90–99.
   PubMed Web of Science ®Google Scholar
• Lash, L. H. and Parker, J. C. 2001. Hepatic and renal toxicities associated with perchloroethylene. Pharmacol. Rev. 53:177–208.
   PubMed Web of Science ®Google Scholar
• Lash, L. H., Qian, W., Putt, D. A., Desai, K., Elfarra, A. A., Sicuri, A. R., and Parker, J. C. 1998a. Glutathione conjugation of perchloroethylene in rats and mice in vitro: Sex-, species-, and tissue-dependent differences. Toxicol. Appl. Pharmacol. 150:49–57.
   PubMed Web of Science ®Google Scholar
• Lash, L. H., Qian, W., Putt, D. A., Hueni, S. E., Elfarra, A. A., Sicuri, A. R., and Parker, J. C. 2002. Renal toxicity of perchloroethylene and S-(1,2,2-trichlorovinyl)glutathione in rats and mice: Sex- and species-dependent differences. Toxicol. Appl. Pharmacol. 179:163–171.
   PubMed Web of Science ®Google Scholar
• Lash, L. H., Qian, W., Putt, D. A., Jacobs, K., Elfarra, A. A., Krause, R. J., and Parker, J. C. 1998b. Glutathione conjugation of trichloroethylene in rats and mice: Sex-, species-, and tissue-dependent differences. Drug Metab. Dispos. 26:12–19.
   PubMed Web of Science ®Google Scholar
• Matuszewski, B. K., Constanzer, M. L., and Chavez-Eng, C. M. 2003. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal. Chem. 75:3019–3030.
   PubMed Web of Science ®Google Scholar
• Moron, M. S., Depierre, J. W., and Mannervik, B. 1979. Levels of glutathione, glutathione reductase and glutathione S-transferase activities in rat lung and liver. Biochim. Biophys. Acta 582:67–78.
   PubMed Web of Science ®Google Scholar
• National Research Council. 2010. Review of the Environmental Protection Agency’s Draft IRIS Assessment of Tetrachloroethylene. Washington, DC:The National Academies Press.
   Google Scholar
• National Toxicology Program. 1977. Bioassay of tetrachloroethylene for possible carcinogenicity. Natl. Cancer Inst. Carcinogen Tech. Rep. Ser. 13:1–83.
   PubMedGoogle Scholar
• Philip, B. K., Mumtaz, M. M., Latendresse, J. R., and Mehendale, H. M. 2007. Impact of repeated exposure on toxicity of perchloroethylene in Swiss Webster mice. Toxicology 232:1–14.
   PubMed Web of Science ®Google Scholar
• Ripp, S. L., Overby, L. H., Philpot, R. M., and Elfarra, A. A. 1997. Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA-expressed flavin-containing mono-oxygenases: Studies with S-(1,2-dichlorovinyl)-L-cysteine, S-(1,2,2-trichlorovinyl)-L-cysteine, S-allyl-L-cysteine, and S-benzyl-L-cysteine. Mol. Pharmacol. 51:507–515.
   PubMed Web of Science ®Google Scholar
• Schaeffer, V. H. and Stevens, J. L. 1987. The transport of S-cysteine conjugates in LLC-PK1 cells and its role in toxicity. Mol. Pharmacol. 31:506–512.
   PubMed Web of Science ®Google Scholar
• Uttamsingh, V., Keller, D. A., and Anders, M. W. 1998. Acylase I-catalyzed deacetylation of N-acetyl-L-cysteine and S-alkyl-N-acetyl-L-cysteines. Chem. Res. Toxicol. 11:800–809.
   PubMed Web of Science ®Google Scholar
• Vamvakas, S., Dekant, W., and Henschler, D. 1989a. Assessment of unscheduled DNA synthesis in a cultured line of renal epithelial cells exposed to cysteine S-conjugates of haloalkenes and haloalkanes. Mutat. Res. 222:329–335.
   PubMed Web of Science ®Google Scholar
• Vamvakas, S., Herkenhoff, M., Dekant, W., and Henschler, D. 1989b. Mutagenicity of tetrachloroethene in the Ames test–metabolic activation by conjugation with glutathione. J. Biochem. Toxicol. 4:21–27.
   PubMedGoogle Scholar
• Volkel, W., Friedewald, M., Lederer, E., Pahler, A., Parker, J., and Dekant, W. 1998. Biotransformation of perchloroethene: dose-dependent excretion of trichloroacetic acid, dichloroacetic acid, and N-acetyl-S-(trichlorovinyl)-L-cysteine in rats and humans after inhalation. Toxicol. Appl. Pharmacol. 153:20–27.
   PubMed Web of Science ®Google Scholar
• Volkel, W., Pahler, A., and Dekant, W. 1999. Gas chromatography-negative ion chemical ionization mass spectrometry as a powerful tool for the detection of mercapturic acids and DNA and protein adducts as biomarkers of exposure to halogenated olefins. J. Chromatogr. A 847:35–46.
   PubMed Web of Science ®Google Scholar
• Whitfield, J. B. 2001. Gamma glutamyl transferase. Crit. Rev. Clin. Lab. Sci. 38:263–355.
   PubMed Web of Science ®Google Scholar
• Yoo, H. S., Bradford, B. U., Kosyk, O., Uehara, T., Shymonyak, S., Collins, L. B., Bodnar, W. M., Ball, L. M., Gold, A., and Rusyn, I. 2015. Comparative analysis of the relationship between trichloroethylene metabolism and tissue-specific toxicity among inbred mouse strains: Kidney effects. J. Toxicol. Environ. Health Part A 78:32–49.
   PubMed Web of Science ®Google Scholar