Mechanisms of Acetaminophen Toxicity: Immunochemical Detection of Drug-Protein Adducts

References

• Boyd E. M., Bereczky G. M. Liver necrosis from paracetamol. Br. J. Pharmacol. 1966; 26: 606–614
   PubMed Web of Science ®Google Scholar
• Davidson D. G. G., Eastham W. N. Acute liver necrosis following overdose of paracetamol. Br. Med. J. 1966; 5512: 497–499
   Web of Science ®Google Scholar
• Thompson J. S., Prescott L. F. Liver damage and impaired glucose tolerance after paracetamol overdosage. Br. Med. J. 1966; 5512: 506–507
   Google Scholar
• Mitchell J. R., Jollow D. J., Potter W. Z., Davis D. C., Gillette J. R., Brodie B. B. Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. J. Pharmacol. Exp. Ther. 1973; 187: 185–194
   PubMed Web of Science ®Google Scholar
• Jollow D. J., Mitchell J. R., Potter W. Z., Davis D. C., Gillette J. R., Brodie B. B. Acetaminophen-induced hepatic necrosis, II. Role of covalent binding in vivo. J. Pharmacol. Exp. Ther. 1973; 757: 195–202
   Google Scholar
• Potter W. Z., Davis D. C., Mitchell J. R., Jollow D. J., Gillette J. R., Brodie B. B. Acetaminophen-induced hepatic necrosis. III. Cytochrome P-450-mediated covalent binding in vitro. J. Pharmacol. Exp. Ther. 1973; 187: 203–210
   PubMed Web of Science ®Google Scholar
• Mitchell J. R., Jollow D. J., Potter W. Z., Gillette J. R., Brodie B. B. Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. J. Pharmacol. Exp. Ther. 1973; 18: 211–217
   Google Scholar
• Jollow D. J., Thorgeirsson S. S., Potter W. Z., Hashimoto M., Mitchell J. R. Acetaminophen-induced hepatic necrosis. IV. Metabolic disposition of toxic and nontoxic doses of acetaminophen. Pharmacology 1974; 12: 251–271
   PubMed Web of Science ®Google Scholar
• Hinson J. A. Biochemical toxicology of acetaminophen. Rev. Biochem. Toxicol 1980; 2: 103–129
   Google Scholar
• Hinson J. A., Pohl L. R., Monks T. J., Gillette J. R. Acetaminophen-induced hepatotoxicity. Life Sci. 1981; 29: 107–116
   PubMed Web of Science ®Google Scholar
• Hinson J. A., Roberts D. W. Role of covalent and noncovalent interactions in cell toxicity: Effects on proteins. Annu. Rev. Pharmacol. Toxicol 1992; 32: 471–510
   PubMed Web of Science ®Google Scholar
• Nelson S. D., Pearson P. G. Covalent and noncovalent interactions in acute lethal cell injury caused by chemicals. Annu. Rev. Pharmacol Toxicol 1990; 30: 169–195
   PubMed Web of Science ®Google Scholar
• Prescott L. F. Paracetamol overdosage. Pharmacological considerations and clinical management. Drugs 1983; 25: 290–314
   PubMed Web of Science ®Google Scholar
• Massey T. E., Racz W. J. Effects of N-acetylcysteine on metabolism, covalent binding, and toxicity of acetaminophen in isolated mouse hepatocytes. Toxicol. Appl. Pharmacol 1981; 93: 378–387
   Google Scholar
• Dahlin D. C., Miwa G. T., Lu A. Y. H., Nelson S. D. N-Acetyl-p-benzoquinone imine: A cytochrome P-450-mediated oxidation product of acetaminophen. Proc. Natl. Acad. Sci., USA 1984; 81: 1327–1331
   PubMed Web of Science ®Google Scholar
• Potter D. W., Hinson J. A. Reactions of N-acetyl-p-benzo-quinone imine with reduced glutathione, acetaminophen, and NADPH. Mol Pharmacol 1986; 30: 33–41
   PubMed Web of Science ®Google Scholar
• Gillette J. R., Nelson S. D., Mulder G. J., Jollow D. J., Mitchell J. R., Pohl L. R., Hinson J. A. Formation of chemically reactive metabolites of phenacetin and acetaminophen. Adv. Exp. Med. Biol 1981; 136(Pt. B)931–950
   PubMedGoogle Scholar
• Raucy J. L., Lasker J. M., Lieber C. S., Black M. Acetaminophen activation by human liver cytochromes P450IIEI and P450IA2. Arch. Biochem. Biophys. 1989; 271: 270–283
   PubMed Web of Science ®Google Scholar
• Patten C. J., Thomas P. E., Guy R. L., Lee M., Gonzalez F. J., Guengerich F. P., Yang C. S. Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. Chem. Res. Toxicol. 1993; 6: 511–518
   PubMed Web of Science ®Google Scholar
• Snawder J. E., Roe A. L., Benson R. W., Roberts D. W. Loss of CYP2E1 and CYP-1A2 activity as a function of acetaminophen dose: Relation to toxicity. Biochem. Biophys. Res. Commun. 1994; 205(1)532–539
   Google Scholar
• Coles B., Wilson I., Wardman P., Hinson J. A., Nelson S. D., Ketterer B. The spontaneous and enzymatic reaction of N-acetyl-p-benzoquinonimine with glutathione: A stopped-flow kinetic study. Arch. Biochem. Biophys. 1988; 264: 253–260
   PubMed Web of Science ®Google Scholar
• Hinson J. A., Monks T. J., Hong M., Highet R. J., Pohl L. R. 3-(Glutathion-S-yl)acetaminophen: A biliary metabolite of acetaminophen. Drug Metab. Dispos. 1982; 10: 47–50
   PubMed Web of Science ®Google Scholar
• Hoffman K. J., Streeter A. J., Axworthy D. B., Baillie T. A. Structural characterization of the major covalent adduct formed in vitro and in vivo between acetaminophen and mouse liver proteins. Mol. Pharmacol. 1985; 27: 566–573
   PubMed Web of Science ®Google Scholar
• Roberts D. W., Pumford N. R., Potter D. W., Benson R. W., Hinson J. A. A sensitive immunochemical assay for acetaminophen-protein adducts. J. Pharmacol. Exp. Ther. 1987; 241: 527–533
   PubMed Web of Science ®Google Scholar
• Potter D. W., Pumford N. R., Hinson J. A., Benson R. W., Roberts D. W. Epitope characterization of acetaminophen bound to protein and nonprotein sulfhydryl groups by an enzyme-linked immunosorben assay. J. Pharmacol. Exp. Ther. 1989; 248: 182–189
   PubMed Web of Science ®Google Scholar
• Pumford N. R., Hinson J. A., Potter D. W., Rowland K. L., Benson R. W., Roberts D. W. Immunochemical quantitation of 3-(cystein-S-yl)acetaminophen adducts in serum and liver proteins of acetaminophen treated mice. J. Pharmacol. Exp. Ther. 1989; 248: 190–196
   PubMed Web of Science ®Google Scholar
• Roberts D. W., Bucci R. J., Benson R. W., Warbritton A. R., McRae T. A., Pumford N. R., Hinson J. A. Immunohistochemical localization and quantification of the 3-(cystein-5-yl)acetaminophen protein adduct in acetaminophen hepatotoxicity. Am. J. Pathol. 1991; 138: 359–371
   PubMed Web of Science ®Google Scholar
• Pumford N. R., Hinson J. A., Benson R. W., Roberts D. W. Immunoblot analysis of protein containing 3-(cystein-S-yl)acetami-nophen adducts in serum and subcellular liver fractions from acetaminophen-treated mice. Toxicol. Appl. Pharmacol 1990; 104: 521–532
   PubMed Web of Science ®Google Scholar
• Hinson J. A., Roberts D. W., Benson R., Dalhoff K., Loft S., Poulsen H. E. Mechanism of paracetamol toxicity. Lancet 1990; 355(8602)732
   Google Scholar
• Pumford N. R., Roberts D. W., Benson R. W., Hinson J. A. Immunochemical quantitation of 3-(cystein-S-yl)acetaminophen protein adducts in subcellular liver fractions following a hepatotoxic dose of acetaminophen. Biochem. Pharmacol. 1990; 40: 573–579
   PubMed Web of Science ®Google Scholar
• Pumford N. R., Martin B. M., Hinson J. A. A metabolite of acetaminophen covalently binds to the 56 kDa selenium binding protein. Biochem. Biophys. Res. Commun. 1992; 182: 1348–1355
   PubMed Web of Science ®Google Scholar
• Medina D., Morrison D. G. Current ideas on selenium as a chemopreventive agent. Pathol. Immunopathol. Res. 1988; 7: 187–199
   PubMedGoogle Scholar
• Bansal M. P., Mukhopadhyay T., Scott J., Mukhopadhyay R. G., Medina D. DNA sequencing of a mouse liver protein that binds selenium: Implications for selenium's mechanism of action in cancer prevention. Carcinogenesis 1990; 11: 2071–2073
   PubMed Web of Science ®Google Scholar
• Pumford N. R., Halmes N. C., Martin B. M., Hinson J. A. Covalent binding to N-10-formyl tetrahydrofolate dehydrogenase following a hepatic dose of acetaminophen. Toxicologist 1994; 14: 426
   Google Scholar
• Cook R. J., Lloyd R. S., Wagner C. Isolation and characterization of cDNA clones for rat liver 10-formyltetrahydrofolate de-hydroganse. J. Biol. Chem. 1991; 266: 4965–4973
   PubMed Web of Science ®Google Scholar