Selective alterations in the patterns of newly synthesized proteins by acetaminophen and its dimethylated analogues in primary cultures of mouse hepatocytes

Toxicology and Applied Pharmacology - Tập 112 - Trang 282-290 - 1992
Mary K. Bruno1, Steven D. Cohen2, Edward A. Khairallah1
1Department of Molecular and Cell Biology, The University of Connecticut, Storrs, Connecticut 06269-3125 USA
2Department of Pharmacology and Toxicology, The University of Connecticut, Storrs, Connecticut 06269-3125 USA

Tài liệu tham khảo

Aikawa, 1978, Comparison of effects of acetaminophen on liver microsomal drug metabolism and lipid peroxidation in rats and mice, Jpn. J. Pharmacol., 28, 485, 10.1254/jjp.28.485 Alam, 1989, Transcriptional activation of the heme oxygenase gene by heme and cadmium in mouse hepatoma cells, J. Biol. Chem., 254, 6371, 10.1016/S0021-9258(18)83358-0 Albano, 1985, Mechanisms of N-acetyl-p-benzoquinone imine cytotoxicity, Mol. Pharmacol., 28, 306 Bartolone, 1987, Immunochemical detection of acetaminophen-bound liver proteins, Biochem. Pharmacol., 36, 1193, 10.1016/0006-2952(87)90069-4 Bartolone, 1988, Immunochemical analysis of acetaminophen covalent binding to proteins: Partial characterization of the major acetaminophenbinding liver proteins, Biochem. Pharmacol., 37, 4763, 10.1016/0006-2952(88)90350-4 Bartolone, 1989, Selective acetaminophen metabolite binding to extrahepatic proteins: An in vivo and in vitro analysis, Toxicol. Appl. Pharmacol., 99, 240, 10.1016/0041-008X(89)90006-9 Beales, 1985, Lipid peroxidation, protein synthesis, and protection by calcium EDTA in paracetamol injury to isolated hepatocytes, Biochem. Pharmacol., 34, 19, 10.1016/0006-2952(85)90094-2 Beierschmitt, 1989, Selective protein arylation and the age dependency of acetaminophen hepatotoxicity in mice, Toxicol. Appl. Pharmacol., 98, 517, 10.1016/0041-008X(89)90180-4 Bergmeyer, 1974, UV-assay with pyruvate and NADH, Vol. 2, 574 Birge, 1988, Dissociation of covalent binding from the oxidative effects of acetaminophen, Biochem. Pharmacol., 37, 3383, 10.1016/0006-2952(88)90686-7 Birge, 1989, Selective protein arylation by acetaminophen and 2,6-dimethylacetaminophen in cultured hepatocytes from phenobarbital-induced and uninduced mice, Biochem. Pharmacol., 38, 4429, 10.1016/0006-2952(89)90653-9 Birge, 1990, Acetaminophen hepatotoxicity: Correspondence of selective protein arylation in human and mouse liver in vitro, in culture, and in vivo, Toxicol. Appl. Pharmacol., 105, 472, 10.1016/0041-008X(90)90150-S Blair, 1980, Paracetamol oxidation: Synthesis and reactivity of N-acetyl-p-benzoquinoneimine, Tetrahedron Lett., 21, 4947, 10.1016/S0040-4039(00)71162-2 Brady, 1990, Posttreatment protection with piperonyl butoxide against acetaminophen hepatotoxicity is associated with changes in selective but not total covalent binding, 689 Bruno, 1988, Antidotal effectiveness of N-acetylcysteine in reversing acetaminophen induced hepatotoxicity, Biochem. Pharmacol., 37, 4310, 10.1016/0006-2952(88)90613-2 Dahlin, 1984, N-acetyl-p-benzo-quinoneimine: A cytochrome P450-mediated oxidation product of acetaminophen, 81, 1327 Farrell, 1980, Structural and functional reconstruction of hepatic cytochrome P-450 in vivo. Reversal of allylisopropylacetamide-mediated destruction of the hemoprotein by exogenous heme, J. Biol. Chem., 255, 10,128, 10.1016/S0021-9258(19)70437-2 Fernando, 1980, Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2,6-dimethyl- and N-acetyl-3,5-dimethyl-p-benzoquinone imines, J. Med. Chem., 23, 1153, 10.1021/jm00185a001 Frazier, 1983, Specific protein synthesis as an indicator of hepatotoxicity, 295 Freeman, 1987, Diamide exposure, thermal resistance, and synthesis of stress (heat shock) proteins, Biochem. Pharmacol., 36, 21, 10.1016/0006-2952(87)90378-9 Freeman, 1989, Glutathione conjugation and induction of a 32,000 dalton stress protein, Biochem. Pharmacol., 38, 299, 10.1016/0006-2952(89)90040-3 Griffith, 1980, Determination of glutathione and glutathione disulfide using glutathione reductase and 2-vinylpyridine, Anal. Biochem., 106, 207, 10.1016/0003-2697(80)90139-6 Guzelian, 1979, Induction of hepatic heme oxygenase activity by bromobenzene, Arch. Biochem. Biophys., 196, 178, 10.1016/0003-9861(79)90564-2 Gwynn, 1979, The effect of paracetamol and other foreign compounds on protein synthesis in isolated adult rat hepatocytes, Biochem. Soc. Trans., 7, 117, 10.1042/bst0070117 Hoffmann, 1985, Identification of the major covalent adduct formed in vitro and in vivo between acetaminophen and mouse liver proteins, Mol. Pharmacol., 27, 566 Ishizawa, 1983, Induction of heme oxygenase in rat liver, J. Biol. Chem., 258, 4220, 10.1016/S0021-9258(18)32609-7 Jollow, 1973, Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo, J. Pharmacol. Exp. Ther., 187, 195 Keyse, 1989, Heme oxygenase is the major 32-kDa stress protein induced in human skin fibroblasts by UVA radiation, hydrogen peroxide, and sodium arsenite, 86, 99 Keyse, 1989, Induction of the heme oxygenase gene in human skin fibroblasts by hydrogen peroxide and UVA (365 nm) radiation: Evidence for the involvement of the hydroxyl radical, Carcinogensis, 11, 787, 10.1093/carcin/11.5.787 Khairallah, 1976, Assessment of protein turnover in perfused rat liver. Evidence for amino acid compartmentation from differential labelling of free and tRNA-bound vali, J. Biol. Chem., 251, 1375, 10.1016/S0021-9258(17)33750-X Kutty, 1988, Rat liver cytochrome P-450b, P-420b, and P-420c are degraded to biliverdin by heme oxygenase, Arch. Biochem. Biophys., 260, 638, 10.1016/0003-9861(88)90492-4 Laemmli, 1970, Cleavage of structural proteins during the assembly of the head bacteriophage T4, Nature, 227, 680, 10.1038/227680a0 Lincoln, 1989, Heme catabolism in cultured hepatocytes: Evidence that heme oxygenase is the predominant pathway and that a proportion of synthesized heme is converted rapidly to biliverdin, Biochem. Biophys. Acta, 992, 49, 10.1016/0304-4165(89)90049-4 Lowry, 1951, Protein measurement with the Folin phenol reagent, J. Biol. Chem., 193, 265, 10.1016/S0021-9258(19)52451-6 Maines, 1988, Heme oxygenase: Function, multiplicity, regulatory mechanisms, and clinical applications, FASEB J., 2, 2557, 10.1096/fasebj.2.10.3290025 Markwell, 1978, A modification of the Lowry procedure to simplify protein determination in membrane and lipoprotein samples, Anal. Biochem., 87, 206, 10.1016/0003-2697(78)90586-9 Nelson, 1990, Covalent and noncovalent interactions in acute lethal cell injury caused by chemicals, Annu. Rev. Pharmacol. Toxicol., 30, 169, 10.1146/annurev.pa.30.040190.001125 Peterson, 1989, The role of heme oxygenase and aryl hydrocarbon hydroxylase in the protection by cysteamine from acetaminophen hepatotoxicity, Toxicol. Appl. Pharmacol., 97, 430, 10.1016/0041-008X(89)90248-2 Placke, 1987, Ultrastructural changes during acute acetaminophen-induced hepatotoxicity in the mouse: A time and dose study, Toxicol. Pathol., 15, 431, 10.1177/019262338701500407 Porubek, 1987, Investigation of the mechanism of acetaminophen toxicity in isolated hepatocytes with the acetaminophen analogues 3,5-dimethylacetaminophen and 2,6-dimethylacetaminophen, Mol. Pharmacol., 31, 647 Pumford, 1990, Immunoblot analysis of protein containing 3-(cystein-s-yl)acetaminophen adducts in serum and subcellular liver fractions from acetaminophentreated mice, Toxicol. Appl. Pharmacol., 104, 521, 10.1016/0041-008X(90)90174-S Rosen, 1984, Reduction and glutathione conjugation reactions of N-acetyl-p-benzoquinoneimine and two dimethylated analogues, Mol. Pharmacol., 25, 151 Rosen, 1983, Acetaminophen hepatotoxicity. An alternative mechanism, Biochem. Pharmacol., 32, 2053, 10.1016/0006-2952(83)90426-4 Schlesinger, 1990, Heat shock proteins, J. Biol. Chem., 265, 12,111, 10.1016/S0021-9258(19)38314-0 Scornik, 1974, In vivo rate of translation by ribosomes of normal and regenerating liver, J. Biol. Chem., 249, 3876, 10.1016/S0021-9258(19)42556-8 Shelton, 1986, Evidence that glutathione participates in the induction of a stress protein, Biochem. Biophys. Res. Commun., 134, 492, 10.1016/S0006-291X(86)80447-8 Stocker, 1987, Bilirubin is an antioxidant of possible physiological importance, Science, 235, 1043, 10.1126/science.3029864 Taketani, 1989, The human 32-kDa stress protein induced by exposure to arsenite and cadmium ions is heme oxygenase, FEBS Lett., 245, 173, 10.1016/0014-5793(89)80215-7 Taketani, 1990, Induction in mouse peritoneal macrophages of 34 kDa stress protein and heme oxygenase by sulfhydryl-reactive reagents, J. Biochem., 108, 28, 10.1093/oxfordjournals.jbchem.a123156 Thorgeirsson, 1976, Biochemical changes after hepatic injury from toxic doses of acetaminophen or furosemide, Pharmacology, 14, 205, 10.1159/000136597 Walker, 1980, Acetaminopheninduced hepatotoxicity in mice, Lab. Invest., 42, 181 Zatloukal, 1988, Induction of heat shock proteins in short-term cultured hepatocytes derived from normal and chronically griseofulvin-treated mice, Hepatology, 8, 607, 10.1002/hep.1840080328