Covalent modification of lipids and proteins in rat hepatocytes and in vitro by thioacetamide metabolites

Chemical Research in Toxicology

Volumn 25, Issue 9, 2012, Pages 1868-1877

  Sarma, Diganta ^a   Hajovsky, Heather ^a   Koen, Yakov M ^a   Galeva, Nadezhda A ^a   Williams, Todd D ^a   Staudinger, Jeffrey L ^a   Hanzlik, Robert P ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE; CARBON 13; CARBON 14; CELL PROTEIN; DIPALMITOYLPHOSPHATIDYLETHANOLAMINE; HYDROGEN PEROXIDE; LIPOSOME; LYSINE; LYSOZYME; TETRAHYDROFURAN; THIOACETAMIDE DERIVATIVE; THIOACETAMIDE S OXIDE; THIOACETAMIDE S,S DIOXIDE; THIOBENZAMIDE; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COVALENT BOND; IN VITRO STUDY; LIVER CELL; MALE; NONHUMAN; PROTEIN MODIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOACTIVITY; RAT;

ANIMALS; CELLS, CULTURED; CHROMATOGRAPHY, THIN LAYER; HEPATOCYTES; MALE; MASS SPECTROMETRY; MURAMIDASE; OXIDATION-REDUCTION; PHOSPHATIDYLETHANOLAMINES; RATS; RATS, SPRAGUE-DAWLEY; THIOACETAMIDE;

RATTUS;

EID: 84866429090     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx3001658     Document Type: Article

References (42)

1. Samuelsson, K., Bergström, M. A., Jonsson, C. A., Westman, G., and Karlberg, A. (2011) Diphenylthiourea, a common rubber chemical, is bioactivated to potent skin sensitizers Chem. Res. Toxicol. 24, 35-44
2. Hanzlik, R. P. (1984) Prediction of Metabolic Pathways: Sulfur Functional Groups, in Foreign Compound Metabolism (Caldwell, J. and Paulson, G. D., Eds.) pp 65-78, Taylor & Francis, London, U.K.
3. Hunter, A. L., Holscher, M. A., and Neal, R. A. (1977) Thioacetamide-induced hepatic necrosis. I. Involvement of the mixed-function oxidase enzyme system J. Pharmacol. Exp. Ther. 200, 439-448 (Pubitemid 8037503)
4. Malvaldi, G. (1977) Liver changes following thiobenzamide poisoning Experientia 33, 1200-1201 (Pubitemid 8175811)
5. Hanzlik, R. P., Vyas, K. P., and Traiger, G. J. (1978) Substituent effects on the hepatotoxicity of thiobenzamide derivatives in the rat Toxicol. Appl. Pharmacol. 46, 685-694 (Pubitemid 9091567)
6. Hanzlik, R. P., Cashman, J. R., and Traiger, G. J. (1980) Relative hepatotoxicity of substituted thiobenzamides and thiobenzamide-s-oxides in the rat Toxicol. Appl. Pharmacol. 55, 260-272 (Pubitemid 10006665)
7. Cashman, J. R., Parikh, K. K., Traiger, G. J., and Hanzlik, R. P. (1983) Relative hepatotoxicity of ortho and meta monosubstituted thiobenzamides in the rat Chem.-Biol. Interact. 45, 342-347
8. Mangipudy, R. S., Chanda, S., and Mehendale, H. (1995) Tissue repair response as a function of dose in thioacetamide hepatotoxicity Environ. Health Perspect. 103, 260-267
9. Okuyama, H., Makamura, H., Shimahara, Y., Uyama, N., Kwon, Y. W., Yamaoka, N., and Yodoi, J. (2002) Overexprssison of thioredoxin prevents thioacetamide-induced hepatic fibrosis in mice J. Hepatol. 42, 117-123
10. Xie, Y., Wang, G., Wang, H., Yao, X., Jiang, S., Kang, A., Zhou, F., Xie, T., and Hao, H. (2012) Cytochrome p450 dysregulations in thioacetamid-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents Drug Metab. Dispos. 40, 796-802
11. Hanzlik, R. P. and Cashman, J. R. (1983) Microsomal metabolism of thiobenzamide and thiobenzamide- S -oxide Drug Metab. Dispos. 11, 210-215
12. Ikehata, K., Duzhak, T. G., Galeva, N. A., Ji, T., Koen, Y. M., and Hanzlik, R. P. (2008) Protein targets of reactive metabolites of thiobenzamide in rat liver in vivo Chem. Res. Toxicol. 21, 1432-1442
13. Ji, T., Ikehata, K., Koen, Y. M., Esch, S. W., Williams, T. D., and Hanzlik, R. P. (2007) Covalent modification of microsomal lipids by thiobenzamide metabolites in vivo Chem. Res. Toxicol. 20, 701-708 (Pubitemid 46762105)
14. Dyroff, M. C. and Neal., R. A. (1981) Identification of the major protein adduct formed in rat liver after thioacetamide administration Cancer Res. 41, 3430-3435 (Pubitemid 11063615)
15. Dyroff, M. C. and Neal, R. A. (1983) Studies of the mechanism of metabolism of thioacetamide S -oxide by rat liver microsomes Mol. Pharmacol. 233, 219-227 (Pubitemid 13184510)
16. Astarita, G., Ahmed, F., and Piomelli, D. (2008) Identification of biosynthetic precursors for the endocannabinoid anandamide in the rat brain J. Lipid Res. 49, 48-57
17. Caramelo, J. J., Forin-Christensen, J., and Delfino, J. M. (2003) Phosphplipase activity on N -acyl phosphatidylethanolamines is critically dependent on the n -acyl chain length Biochem. J. 374, 109-115 (Pubitemid 37046934)
18. Guo, L., Amarnath, V., and Davies, S. (2010) A liquid chromatography-tandem mass spectrometry method for measurement of N -modified phosphatidylethanolamines Anal. Biochem. 405, 236-245
19. Hansen, H. S., Moesgaard, B., Petersen, G., and Hanses, H. K. (2002) Putative neuroprotective actions of N -acyl-ethanolamines Pharmacol. Ther. 95, 119-126
20. Sarma, D. and Hanzlik, R. P. (2011) Synthesis of carbon-14, carbon-13 and deuterium labeled forms of thioacetamide and thioacetamide S -oxide J. Labelled Compd. Radiopharm. 54, 795-798
21. Stone, K. L. and Williams, K. R. (2002) Enzymatic Digestion of Proteins in Solution and in SDS Polyacrylamide Gels, in The Protein Protocols Handbook (Walker, J. M., Eds.) 2 nd ed., pp 512-521, Humana Press, Totowa, NJ.
22. Mudra, D. R. and Parkinson, A. (2001) Preparation of hepatocytes Curr. Protoc. Toxicol. 14.2, 1-13
23. Bligh, E. G. and Dyer, W. J. (1959) A rapid method of total lipid extraction and purification Can. J. Biochem. Physiol. 37, 911-917
24. Brügger, B., Erben, G., Sandhoff, R., Wieland, F. T., and Lehmann, W. D. (1997) Quantitative analysis of biological membrane lipids at the low picomole level by nano-electrospray ionization tandem mass spectrometry Proc. Natl. Acad. Sci. U.S.A. 94, 2339-2344 (Pubitemid 27136876)
25. DeLong, C. J., Baker, P. R. S., Samuel, M., Cui, Z., and Thomas, M. J. (2001) Molecular species composition of rat liver phospholipids by ESI-MS/MS: The effect of chromatography J. Lipid Res. 42, 1959-1968 (Pubitemid 34001044)
26. Chowdhury, S. K., Katta, V., Beavis, R. C., and Chait, B. T. (1990) Origin and removal of adducts (molecular mass = 98 u) attached to peptide and protein ions in electrospray ionization mass spectra J. Am. Soc. Mass Spectrom. 1, 382-388
27. Winger, B. E., Hofstadler, S. A., Bruce, J. E., Udseth, H. R., and Smith, R. D. (1993) High-resolution accurate mass measurements of biomolecules using a new electrospray ionization ion cyclotron resonance mass spectrometer J. Am. Soc. Mass Spectrom. 4, 566-577
28. Hanzlik, R. P., Harriman, S. P., and Frauenhoff, M. M. (1994) Covalent binding of benzoquinone to reduced ribonuclease. Adduct structures and stoichiometry Chem. Res. Toxicol. 7, 177-184 (Pubitemid 24105349)
29. Fitzhugh, O. G. and Nelson, A. A. (1943) Liver tumors in rats fed thiourea or thioacetamide Science 108, 626-628
30. Yeh, T.-S., Ho, Y.-P., Huang, S. F., Yeh, J.-N., Jan, Y.-Y., and Chen, M.-F. (2004) Thalidomide salvages lethal hepatic necroinflamation and accelerates recovery from cirrhosis in rats J. Hepatol. 41, 606-612 (Pubitemid 39297796)
31. Rees, K. R., Rowland, G. F., and Varcoe, J. S. (1966) The metabolism of tritiated thioacetamide in the rat Int. J. Cancer 1, 197-206
32. http://tpdb.medchem.ku.edu:8080/protein-database/.
33. Guastadisegni, C., Guidoni, L., Balduzzi, M., Viti, V., Di Consiglio, E., and Vittozzi, L. (1998) Characterization of a phospholipid adduct formed in Sprague Dawley rats by chloroform metabolism: Nmr studies J. Biochem. Mol. Toxicol. 12, 93-102 (Pubitemid 128480782)
34. Müller, R. and Stier, A. (1982) Modification of liver microsomal lipids by halothane metabolites: A multi nuclear nmr spectrscopic study Naunyn-Schmiedeberg's Arch. Pharmacol. 321, 234-237 (Pubitemid 13204359)
35. Hayden, P. J., Welsh, C. J., Yang, Y., Schaefer, W. H., Ward, A. J. I., and Stevens, J. L. (1992) Formation of mitochondrial phospholipid adducts by nephrotoxic cysteine conjugate metabolites Chem. Res. Toxicol. 5, 231-237
36. Yin, H., Xu, L., and Porter, N. A. (2011) Free radical lipid peroxidation: Mechanisms and analysis Chem. Rev. 111, 5944-5972
37. Bacot, S., Bernoud-Hubac, N., Baddas, N., Chantegrel, B., Deshayes, C., Doutheau, A., Lagarde, M., and Guichardant, M. (2003) Covalent binding of hydroxy-alkenals 4-HDDE, 4-HHE, and 4-NHE to ethanolamine phospholipid subclasses J. Lipid Res. 44, 917-926 (Pubitemid 37279652)
38. Sullivan, C. B., Matafonova, E., Roberts, L. J., II, Amarnath, V., and Davies, S. S. (2010) Isoketals form cytotoxic phosphatidylethanolamine adducts in cells J. Lipid Res. 51, 999-1009
39. Hansen, H. S., Moesgaard, B., Hansen, H. H., Schousboe, A., and Petersen, G. (1999) Formation of N -acyl-phosphatidylethanolamine and n-acylethanolamine (including anandamide) during glutamate-induced neurotoxicity Lipids 34, S327-S330
40. Guo, L., Chen, Z., Cox, B. E., Amarnath, V., Epand, R. F., Epand, R. M., and Davies, S. (2011) Phosphatidylethanolamines modified by γ-ketoaldehyde induce endoplasmic reticulum stress and endothelial activation J. Biol. Chem. 286, 18170-18180
41. Marsh, D. (1998) Chain-melting transition temperatures of phospholipids with acylated or alkylated headgroups (n-acyl phosphatidylethanolamines and O -alkyl phosphatidic acids), or with α-branched chains Biochim. Biophys. Acta 1414, 249-254 (Pubitemid 28511055)
42. Choudhary, C., Kumar, C., Gnad, F., Nielsen, M. L., Rehman, M., Walther, T. C., Olsen, J. V., and Mann, M. (2009) Lysine acetylation targets protein complexes and co-regulates major cellular functions Science 325, 834-840