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Chemical Compound Review:

DCVG (2S)-2-amino-4-[[(1S)-1...

Synonyms: CCRIS 2074, LS-72443, AC1O5NJ7, C14868, 96614-59-4, ...

Lash, L.H. et al., Elfarra, A.A. et al., Cummings, B.S. et al., Lash, L.H. et al., Lash, L.H. et al., et al.

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Disease relevance of DCVG

Glutathione (GSH) conjugation of trichloroethylene (Tri) to form S-(1,2-dichlorovinyl)glutathione (DCVG) has been implicated in the nephrotoxicity and nephrocarcinogenicity of Tri. Marked sex- and species-dependent differences exist, however, in the susceptibility to Tri-induced renal toxicity, with the male rat being the most susceptible [1].

High impact information on DCVG

S-(1,2-Dichlorovinyl)glutathione (DCVG) and S-(1,2-dichlorovinyl)-L-cysteine (DCVC) produced time- and concentration-dependent cell death in isolated rat kidney proximal tubular cells [2].
Hyperpolarization of the membrane potential to -60 mV in the presence of sodium stimulated uptake another 2.7-fold, indicating that cotransport of sodium and S-(1,2-dichlorovinyl)glutathione is electrogenic [3].
These results strongly support a role for renal gamma-glutamyl transpeptidase, cysteine conjugate beta-lyase, and organic anion transport systems in S-(1,2-dichlorovinyl)glutathione- and S-(1,2-dichlorovinyl)cysteine-induced nephrotoxicity [4].
The kinetics of Tri metabolism to its GSH conjugate S-(1,2-dichlorovinyl)glutathione (DCVG) followed biphasic kinetics, with apparent Km and Vmax values of 0.51 and 24.9 mM and 0.10 and 1.0 nmol/min per mg protein, respectively [5].
Tri metabolism to S-(1,2-dichlorovinyl)glutathione (DCVG), a nephrotoxic metabolite of Tri, was demonstrated in both isolated hepatocytes and kidney cells [6].

References

Glutathione conjugation of trichloroethylene in rats and mice: sex-, species-, and tissue-dependent differences. Lash, L.H., Qian, W., Putt, D.A., Jacobs, K., Elfarra, A.A., Krause, R.J., Parker, J.C. Drug Metab. Dispos. (1998) [Pubmed]
Cytotoxicity of S-(1,2-dichlorovinyl)glutathione and S-(1,2-dichlorovinyl)-L-cysteine in isolated rat kidney cells. Lash, L.H., Anders, M.W. J. Biol. Chem. (1986) [Pubmed]
Uptake of the glutathione conjugate S-(1,2-dichlorovinyl)glutathione by renal basal-lateral membrane vesicles and isolated kidney cells. Lash, L.H., Jones, D.P. Mol. Pharmacol. (1985) [Pubmed]
Mechanism of S-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity. Elfarra, A.A., Jakobson, I., Anders, M.W. Biochem. Pharmacol. (1986) [Pubmed]
Metabolism and toxicity of trichloroethylene and S-(1,2-dichlorovinyl)-L-cysteine in freshly isolated human proximal tubular cells. Cummings, B.S., Lash, L.H. Toxicol. Sci. (2000) [Pubmed]
Glutathione-dependent metabolism of trichloroethylene in isolated liver and kidney cells of rats and its role in mitochondrial and cellular toxicity. Lash, L.H., Xu, Y., Elfarra, A.A., Duescher, R.J., Parker, J.C. Drug Metab. Dispos. (1995) [Pubmed]

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