Relationship between paracetamol binding to and its oxidation by two cytochromes P-450 isozymes—a proton nuclear magnetic resonance and spectrophotometric study

References

• BovD, E. M., and REFtECZKY, G. M., 1966, Liver necrosis from paracetamol. British Journal of Pharmacology, 26, 606–614.
   Web of Science ®Google Scholar
• BURKE, M. D., and MAYER, R. T., 1975, Inherent specificities of purified cytochromes P-450 and P-448 towards biphenyl hydroxylation and ethoxyresorufin deethylation. Drug Metabolism and Disposition, 3, 245–253.
   PubMed Web of Science ®Google Scholar
• COCHIN, J., and AXELROD, J., 1959, Biochemical and pharmacological changes in the rat following chronic administration of morphine, nalorphine and normorphine. Journal of Pharmacology and Experi-mental Therapeutics, 125, 105–110.
   PubMed Web of Science ®Google Scholar
• ELSHOURBAGY, N. A., and GUZELIAN, P. S., 1980, Separation, purification and characterization of a novel form of hepatic cytochrome P-450 from rats treated with pregnenolone-16-a-carbonitril. Journal of Biological Chemistry, 255, 1279–1285.
   PubMed Web of Science ®Google Scholar
• GIBSON, G. G., and TAMBURINI, P. P., 1984, Cytochrome P-450 spin-state: inorganic biochemistry of haem iron ligation and functional significance. Xenobiotica, 14, 27–48.
   PubMed Web of Science ®Google Scholar
• GUENGERICH, F. P., and MADDoNALD, T. L., 1984, Chemical mechanisms of catalysis by cytochrome P-450: a unified view. Accounts of Chemical Research, 17, 9–16.
   Web of Science ®Google Scholar
• HINSON, J. A., 1980, Biochemical toxicology of acetaminophen. In Reviews in Biochemical Toxicology, Vol. 2, edited by E. Hodgson, J. R. Bend and R. M. Philpot (Amsterdam: Elsevier), pp. 103–129.
   Google Scholar
• HINSON, J. A., POHL, L. R., MONKS, T. J., and Glt.i.Errs, J. R., 1980, 3-Hydroxyacetaminophen: a microsomal metabolite of acetaminophen. Drug Metabolism and Disposition, 8, 289–294. HINSON, J. A., POHL, L. R., MONKS, T. J., and GILLETTE, J. R., 1981, Mini-review: acetaminophen-induced hepatotoxicity. Life Sciences, 29, 107–116.
   Google Scholar
• HOLLENBERG, P. F., MIWA, G. T., WALSH, J. S., DWYER, L. A., RICKERT, D. E., and KEDDEnts, G. L., 1985, Mechanisms of N-demethylation reactions catalyzed by cytochrome P-450 and peroxidases. Drug Metabolism and Disposition, 13, 272–275.
   PubMed Web of Science ®Google Scholar
• IOANNIDES, C., STEELE, C. M., and PARKE, D. V., 1983, Species variation in the metabolic activation of paracetamol to toxic intermediates: role of cytochromes P-450 and P-448. Toxicology Letters, 16, 55–61.
   PubMed Web of Science ®Google Scholar
• JARDETZKY, O., and ROBERTS, G. C. K., 1981. Protein-ligand interactions. In N.m.r. in Molecular Biology (New York: Academic Press), pp. 379–416.
   Google Scholar
• KLOTZ, A. V., STEGEMAN, J. J., and WALSH, C., 1984, An alternative 7-ethoxyresorufin O-deethylase activity assay: a continuous visible spectrophotometric method for measurement of cytochrome P-450 monooxygenase activity. Analytical Biochemistry, 140, 138–145.
   PubMed Web of Science ®Google Scholar
• LOEW, G. H., and GOLDBLUM, A., 1985, Metabolic activation and toxicity of acetaminophen and related analogs, a theoretical study. Molecular Pharmacology, 27, 375–386.
   PubMed Web of Science ®Google Scholar
• MACDONALD, T. L., BURKA, L. T., WRIGHT, S. T., and GUENGERICH, F. P., 1982, Mechanisms of hydroxylation by cytochrome P-450: exchange of iron-oxygen intermediates with water. Biochemical and Biophysical Research Communications, 104, 620–625.
   PubMed Web of Science ®Google Scholar
• MILDVAN, A. S., and GUPTA, R. K., 1978, Nuclear relaxation measurements of the geometry of enzyme-bound substrates and analogs. Methods in Enzymology, 49, 322–359.
   PubMedGoogle Scholar
• MOLDEUS, P., 1978, Paracetamol metabolism and toxicity in isolated hepatocytes from rat and mouse. Biochemical Pharmacology, 27, 2859–2863.
   PubMed Web of Science ®Google Scholar
• NELSON, S. D., FORTE, A. J., and DAHLIN, D. C., 1980, Lack of evidence for N-hydroxylacetaminophen as a, reactive metabolite of acetaminophen in vitro. Biochemical Pharmacology, 29, 1617–1620.
   PubMed Web of Science ®Google Scholar
• NOVAK, R. F., and Vnists, K. P., 1982, Proton fourier transform nuclear magnetic resonance relaxation rate studies on the interaction of acetanilide with purified isozymes of rabbit liver microsomal cytochrome P-450 and with cytochrome b5. Molecular Pharmacology, 21, 701–709.
   PubMed Web of Science ®Google Scholar
• PRESCOTT, L. F., Wm GI rr, N., Roscor, P., and BaowN S S, 1971, Plasma paracetamol half-live and hepatic necrosis in patients with paracetamol overdosage. Lancet, 1, 519–522.
   Google Scholar
• PUDZIANOWSKI, A. T., and LOEW, G. H., 1982, Quantum chemical studies of model cytochrome P-450 hydrocarbon oxidation mechanisms II. Mechanisms and relative kinetics of oxene reactions with alkenes. Journal of Molecular Catalysis, 17, 1–22.
   Google Scholar
• PUDZIANOWSKI, A. T., and LOEW, G. H., 1983, Mechanistic studies of oxene reactions with organic substrates: reaction paths on MNDO enthalpy surfaces: models for cytochrome P-450. Inter-national Journal of Quantum Chemistry, 23, 1257–1268.
   Web of Science ®Google Scholar
• SCHENKMAN, J. B., REMMER, H., and ESTABROOK, R. W., 1967, Spectral studies of drug interaction with hepatic microsomal cytochrome P-450. Molecular Pharmacology, 3, 113–123.
   PubMed Web of Science ®Google Scholar
• SCHENKMAN, J. B., CINTI, D. L., ORRENIUS, S., MOLDEUS, P., and KAscHNITz, R., 1972, The nature of reverse type I (modified type II) spectral change in liver microsomes. Biochemistry, 11,4243–4251.
   PubMed Web of Science ®Google Scholar
• SCHENKMAN, J. B., CINTI, D. L., MOLDEUS, P. W., and ORRENIU S., 1973, Newer aspects of substrate binding to cytochrome 13-450. Drug Metabolism and Disposition, 1, 111–120.
   PubMed Web of Science ®Google Scholar
• SCHENKMAN, J. B., SUGAR, S. G., and CINTI, D. L., 1982, Substrate interaction with cytochrome P-450. In Hepatic Cytochrome P-450 Monooxygenase System, edited by J. B. Schenkman and D. Kupfer (Oxford: Pergamon Press), pp. 587–617.
   Google Scholar
• STEELE, C. M., MASSON, H. A., BArrEitsHILL, J. M., GIBSON, G. G., and IOANNIDES, C., 1983, Metabolic activation of paracetamol by highly purified forms of cytochrome P-450. Research Communications in Chemical Pathology and Pharmacology, 40, 109–119.
   PubMedGoogle Scholar
• VLASUK, G. P., GHARAYEB, J., RYAN, D. E., REIK, L., THOMAS, P. E., LVIN, W., and WALTZ, F. G., 1982, Multiplicity, strain differences, and topology of phenobarbital-induced cytochrome P-450 in the rat liver. Biochemistry, 21, 789–798.
   PubMed Web of Science ®Google Scholar
• DE VRIES, J., 1981, I lepatotoxic metabolic activation of paracetamol and its derivatives phenacetin and benorilate: oxygenation or electron transfer. Biomechanical Pharmacology, 30, 399 402.
   Google Scholar
• WEST, P. R., HARMAN, L. S., JOSEPHY, P. D., and MASON, R. P., 1984, Acetaminophen: enzymatic formation of a transient phenoxyl free radical. Biochemical Pharmacology, 33, 2933–2936.
   PubMed Web of Science ®Google Scholar
• WAXMAN, D. J., and WALSH, C., 1982, Phenobarbital-induced rat liver cytochrome P-450. Journal of Biological Chemistry, 257, 10446–10457.
   PubMed Web of Science ®Google Scholar
• WOLDIVIAN, Y. Y., WEINER, L. M. GULYAEVA, L. F., and LYAKHOVICH, V. V., 1985, Proton-NMR study of the interaction of aminopyrine with purified rat liver microsomal cytochrome P-450. FEBS Lett., 181, 295–299.
   PubMed Web of Science ®Google Scholar
• WOLF, C. R., and OESCH, F., 1983, Isolation of a high spin form of cytochrome P-450 induced in rat liver by 3-methylcholanthrene. Biochemical and Biophysical Research Communications, 111, 504–511.
   PubMed Web of Science ®Google Scholar
• YASUKOCHI, Y., and MASTERS, B. S. S., 1976, Some properties of detergent-solubilized NADPH-cytochrome c (cytochrome P-450) reductase purified by biospecific affinity chromatography. Journal of Biological Chemistry, 251, 5337–5344.
   PubMed Web of Science ®Google Scholar