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Chemical Compound Review:

CCRIS 5243 (2S)-2-amino-3-(1,1,2,2...

Synonyms: AG-H-91249, AC1L2XYN, CTK5H7164, LS-188863, 94840-66-1, ...

Hayden, P.J. et al., Cooper, A.J. et al., Schaaf, G.J. et al., Zhang, G. et al., Groves, C.E. et al., et al.

Schaaf, de Groene, Maas, Commandeur, Fink-Gremmels, Cooper, Pinto,

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Disease relevance of CCRIS 5243

DPPD was able to block the toxicity of two other toxic cysteine conjugates S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine and S-(1,1,2,2-tetrafluoroethyl)-L-cysteine [1].

High impact information on CCRIS 5243

Mitochondrial HSP60 (P1 protein) and a HSP70-like protein (mortalin) are major targets for modification during S-(1,1,2,2-tetrafluoroethyl)-L-cysteine-induced nephrotoxicity [2].
A role for fibroblast growth factor type-1 in nephrogenic repair. Autocrine expression in rat kidney proximal tubule epithelial cells in vitro and in the regenerating epithelium following nephrotoxic damage by S-(1,1,2,2-tetrafluoroethyl)-L-cysteine in vivo [3].
Mitochondrial aconitase modification, functional inhibition, and evidence for a supramolecular complex of the TCA cycle by the renal toxicant S-(1,1,2,2-tetrafluoroethyl)-L-cysteine [4].
19F NMR spectroscopy was used in conjunction with isotopic labeling to demonstrate that difluorothionoacetyl-protein adducts are formed by metabolites of the nephrotoxic cysteine conjugate S-(1,1,2,2-tetrafluoroethyl)-L-cysteine (TFEC) [5].
Formation of difluorothionoacetyl-protein adducts by S-(1,1,2,2-tetrafluoroethyl)-L-cysteine metabolites: nucleophilic catalysis of stable lysyl adduct formation by histidine and tyrosine [5].

Chemical compound and disease context of CCRIS 5243

The relationship between the covalent binding, uptake, and toxicity produced by S-(1,2-dichlorovinyl)-L-cysteine (DCVC) and S-(1,1,2,2-tetrafluoroethyl)-L-cysteine (TFEC) was investigated in suspensions of rabbit renal proximal tubules (RPT) [6].

Biological context of CCRIS 5243

Activity of the phase II biotransformation enzymes GST, GGT, beta-lyase and UGT was determined with 1-chloro-2,4-dinitrobenzene, L-glutamic acid gamma-(7-amido-4-methyl-coumarin), S-(1,1,2,2-tetrafluoroethyl)-L-cysteine and 1-naphthol, respectively, as marker substrates [7].

Anatomical context of CCRIS 5243

Inhibition of select mitochondrial enzymes in PC12 cells exposed to S-(1,1,2,2-tetrafluoroethyl)-L-cysteine [8].
An interesting side finding of the present work is that rat liver mitochondria are more active than rat liver cytosol in catalyzing a cysteine S-conjugate beta-lyase reaction with the mitochondrial protoxicant S-(1,1,2,2-tetrafluoroethyl)-L-cysteine (TFEC) at physiological pH and at low substrate concentration [9].

Gene context of CCRIS 5243

We investigated the role of FGF-7 in repair of proximal tubular damage caused by S-(1,1,2,2-tetrafluoroethyl)-L-cysteine (TFEC) [10].

References

The mechanism of cysteine conjugate cytotoxicity in renal epithelial cells. Covalent binding leads to thiol depletion and lipid peroxidation. Chen, Q., Jones, T.W., Brown, P.C., Stevens, J.L. J. Biol. Chem. (1990) [Pubmed]
Mitochondrial HSP60 (P1 protein) and a HSP70-like protein (mortalin) are major targets for modification during S-(1,1,2,2-tetrafluoroethyl)-L-cysteine-induced nephrotoxicity. Bruschi, S.A., West, K.A., Crabb, J.W., Gupta, R.S., Stevens, J.L. J. Biol. Chem. (1993) [Pubmed]
A role for fibroblast growth factor type-1 in nephrogenic repair. Autocrine expression in rat kidney proximal tubule epithelial cells in vitro and in the regenerating epithelium following nephrotoxic damage by S-(1,1,2,2-tetrafluoroethyl)-L-cysteine in vivo. Zhang, G., Ichimura, T., Maier, J.A., Maciag, T., Stevens, J.L. J. Biol. Chem. (1993) [Pubmed]
Mitochondrial aconitase modification, functional inhibition, and evidence for a supramolecular complex of the TCA cycle by the renal toxicant S-(1,1,2,2-tetrafluoroethyl)-L-cysteine. James, E.A., Gygi, S.P., Adams, M.L., Pierce, R.H., Fausto, N., Aebersold, R.H., Nelson, S.D., Bruschi, S.A. Biochemistry (2002) [Pubmed]
Formation of difluorothionoacetyl-protein adducts by S-(1,1,2,2-tetrafluoroethyl)-L-cysteine metabolites: nucleophilic catalysis of stable lysyl adduct formation by histidine and tyrosine. Hayden, P.J., Yang, Y., Ward, A.J., Dulik, D.M., McCann, D.J., Stevens, J.L. Biochemistry (1991) [Pubmed]
Differential cellular effects in the toxicity of haloalkene and haloalkane cysteine conjugates to rabbit renal proximal tubules. Groves, C.E., Hayden, P.J., Lock, E.A., Schnellmann, R.G. J. Biochem. Toxicol. (1993) [Pubmed]
Characterization of biotransformation enzyme activities in primary rat proximal tubular cells. Schaaf, G.J., de Groene, E.M., Maas, R.F., Commandeur, J.N., Fink-Gremmels, J. Chem. Biol. Interact. (2001) [Pubmed]
Inhibition of select mitochondrial enzymes in PC12 cells exposed to S-(1,1,2,2-tetrafluoroethyl)-L-cysteine. Park, L.C., Gibson, G.E., Bunik, V., Cooper, A.J. Biochem. Pharmacol. (1999) [Pubmed]
Aminotransferase, L-amino acid oxidase and beta-lyase reactions involving L-cysteine S-conjugates found in allium extracts. Relevance to biological activity? Cooper, A.J., Pinto, J.T. Biochem. Pharmacol. (2005) [Pubmed]
Induction of FGF-7 after kidney damage: a possible paracrine mechanism for tubule repair. Ichimura, T., Finch, P.W., Zhang, G., Kan, M., Stevens, J.L. Am. J. Physiol. (1996) [Pubmed]

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