Reversibility of covalent electrophile-protein adducts and chemical toxicity

Chemical Research in Toxicology

Volumn 21, Issue 12, 2008, Pages 2361-2369

  Lin, De ^a   Saleh, Samir ^a   Liebler, Daniel C ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOTIN; CYSTEINE; ELECTROPHILE; GLUTATHIONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

APOPTOSIS; ARTICLE; CELL LYSATE; CHEMICAL STRUCTURE; HUMAN; HUMAN CELL; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICHAEL ADDITION; PROTEIN MODIFICATION; PROTEIN STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; SIGNAL TRANSDUCTION;

BIOTIN; CELL EXTRACTS; CELL LINE; CELL SURVIVAL; COLD TEMPERATURE; DNA REPAIR; GLUTATHIONE; HOT TEMPERATURE; HUMANS; KIDNEY; PROTEIN BINDING; PROTEINS; TIME FACTORS;

EID: 58149096589     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx800248x     Document Type: Article

References (28)

1. Guengerich, F. P. (2001) Forging the links between metabolism and carcinogenesis. Mutat. Res. 488, 195-209.
2. Marnett, L. J., Riggins, J. N., and West, J. D. (2003) Endogenous generation of reactive oxidants and electrophiles and their reactions with DNA and protein. J. Clin. Invest. 111, 583-593.
3. Sayre, L. M., Lin, D., Yuan, Q., Zhu, X., and Tang, X. (2006) Protein adducts generated from products of lipid oxidation: Focus on HNE and one. Drug Metab. Rev. 38, 651-675.
4. Liebler, D. C. (2008) Protein damage by reactive electrophiles: Targets and consequences. Chem. Res. Toxicol. 21, 117-128.
5. Evans, D. C., Watt, A. P., Nicoll-Griffith, D. A., and Baillie, T. A. (2004) Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem. Res. Toxicol. 17, 3-16.
6. Dinkova-Kostova, A. T., Holtzclaw, W. D., and Kensler, T. W. (2005) The role of Keap1 in cellular protective responses. Chem. Res. Toxicol. 18, 1779-1791.
7. Nakamura, T., and Lipton, S. A. (2007) S-Nitrosylation and uncompetitive/ fast off-rate (UFO) drug therapy in neurodegenerative disorders of protein misfolding. Cell Death Differ. 14, 1305-1314.
8. Kemp, M., Go, Y. M., and Jones, D. P. (2008) Nonequilibrium thermodynamics of thiol/disulfide redox systems: A perspective on redox systems biology. Free Radical Biol. Med. 44, 921-937.
9. Dennehy, M. K., Richards, K. A. M., Wernke, G. W., Shyr, Y., and Liebler, D. C. (2006) Cytosolic and nuclear protein targets of thiol-reactive electrophiles. Chem. Res. Toxicol. 19, 20-29.
10. Shin, N. Y., Liu, Q., Stamer, S. L., and Liebler, D. C. (2007) Protein targets of reactive electrophiles in human liver microsomes. Chem. Res. Toxicol. 20, 859-867.
11. Wong, H. L., and Liebler, D. C. (2008) Mitochondrial protein targets of thiol-reactive electrophiles. Chem. Res. Toxicol. 21, 796-804.
12. Hong, F., Sekhar, K. R., Freeman, M. L., and Liebler, D. C. (2005) Specific patterns of electrophile adduction trigger Keap1 ubiquitination and Nrf2 activation. J. Biol. Chem. 280, 31768-31775.
13. Codreanu, S. G., Adams, D. G., Dawson, E. S., Wadzinski, B. E., and Liebler, D. C. (2006) Inhibition of protein phosphatase 2A activity by selective electrophile alkylation damage. Biochemistry 45, 10020-10029.
14. Rachakonda, G., Xiong, Y., Sekhar, K. R., Stamer, S. L., Liebler, D. C., and Freeman, M. L. (2008) Covalent modification at Cys151 dissociates the electrophile sensor Keap1 from the ubiquitin ligase CUL3. Chem. Res. Toxicol. 21, 705-710.
15. Eggler, A. L., Liu, G., Pezzuto, J. M., van Breemen, R. B., and Mesecar, A. D. (2005) Modifying specific cysteines of the electrophile-sensing human Keap1 protein is insufficient to disrupt binding to the Nrf2 domain Neh2. Proc. Natl. Acad. Sci. U.S.A. 102, 10070-10075.
16. Prior, I. A., and Clague, M. J. (2000) Detection of thiol modification following generation of reactive nitrogen species: Analysis of synaptic vesicle proteins. Biochim. Biophys. Acta 1475, 281-286.
17. Luo, Y., Eggler, A. L., Liu, D., Liu, G., Mesecar, A. D., and van Breemen, R. B. (2007) Sites of alkylation of human Keap1 by natural chemoprevention agents. J. Am. Soc. Mass Spectrom. 18, 2226-2232.
18. Eggler, A. L., Luo, Y., van Breemen, R. B., and Mesecar, A. D. (2007) Identification of the highly reactive cysteine 151 in the chemopreventive agent-sensor Keap1 protein is method-dependent. Chem. Res. Toxicol. 20, 1878-1884.
19. Sturdik, E., and Drobnica, L. (1981) Interaction of cytotoxic antibiotic dactylarin with glycolytic thiol enzymes in Ehrlich ascites carcinoma cells. J. Antibiot. (Tokyo) 34, 708-712.
20. Wang, Q., Chan, T. R., Hilgraf, R., Fokin, V. V., Sharpless, K. B., and Finn, M. G. (2003) Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. J. Am. Chem. Soc. 125, 3192-3193.
21. Speers, A. E., and Cravatt, B. F. (2004) Profiling enzyme activities in vivo using click chemistry methods. Chem. Biol. 11, 535-546.
22. Nelson, S. D., and Pearson, P. G. (1990) Covalent and noncovalent interactions in acute lethal cell injury caused by chemicals. Annu. Rev. Pharmacol. Toxicol. 30, 169-195.
23. Khan, M. N. (1984) Kinetics and mechanism of the alkaline hydrolysis of maleimide. J. Pharm. Sci. 73, 1767-1771.
24. Khalaf, A. I., Linaza, S., Pitt, A. R., Stimson, W. H., and Suckling, C. J. (2000) On the specificity of reactions catalysed by the antibody H11. Tetrahedron 56, 489-495.
25. Kalia, J., and Raines, R. T. (2007) Catalysis of imido group hydrolysis in a maleimide conjugate. Bioorg. Med. Chem. Lett. 17, 6286-6289.
26. Hamajima, N., Matsuda, K., Sakata, S., Tamaki, N., Sasaki, M., and Nonaka, M. (1996) A novel gene family defined by human dihydropyrimidinase and three related proteins with differential tissue distribution. Gene 180, 157-163.
27. Morgan, A. S., Sanderson, P. E., Borch, R. F., Tew, K. D., Niitsu, Y., Takayama, T., Von Hoff, D. D., Izbicka, E., Mangold, G., Paul, C., Broberg, U., Mannervik, B., Henner, W. D., and Kauvar, L. M. (1998) Tumor efficacy and bone marrow-sparing properties of TER286, a cytotoxin activated by glutathione S-transferase. Cancer Res. 58, 2568-2575.
28. Baillie, T. A. (2006) Future of toxicology-metabolic activation and drug design: Challenges and opportunities in chemical toxicology. Chem. Res. Toxicol. 19, 889-893.