The metabolic activation of abacavir by human liver cytosol and expressed human alcohol dehydrogenase isozymes

Riley, 1995, In vitro analysis of metabolic predispositon to drug hypersensitivity reactions, Clin. Exp. Immunol., 99, 1, 10.1111/j.1365-2249.1995.tb03463.x Pohl, 1998, The immunological and metabolic basis of drug hypersensitivites, Ann. Rev. Pharmacol., 28, 367, 10.1146/annurev.pa.28.040188.002055 Uetrecht, 1999, New concepts in Immunology relevant to idiosycratic drug reactions: The ‘Danger Hypothesis’ and innate immune system, Chem. Res. Toxicol., 12, 387, 10.1021/tx980249i Hess, 1997, The role of reactive metabolites in immune-mediated adverse drug reactions, Annal. Pharmacol., 31, 1378, 10.1177/106002809703101116 Parks, 1990, Drug-protein conjugation and its immunological consequences, Drug Metab. Rev., 22, 87, 10.3109/03602539008991445 Hetherington, S. McGuik, G. Powell, A. Cutrell, O. Naderer. B. Spreen, S. Lafon, G. Pierce, and H. Steel 2001. Hypersensitivity reactions during therapy with the nucleoside reverse transcriptase inhibitor, abacavir. Clinical Therapeutics. (in press). Hinson, 1992, Role of covalent and non-covalent interactions in cell toxicity: effects on proteins, Ann. Rev. Pharmacol. Toxicol., 32, 471, 10.1146/annurev.pa.32.040192.002351 McDowell, 1999, Pharmacokinetics of [14C]-abacavir, a human immunodeficiency virus type 1 (HIV-1) reverse transcriptase inhibitor, administered in a single oral dose to HIV-1 infected adults: a mass balance study, Antimicrob. Agents Chemother., 43, 2855, 10.1128/AAC.43.12.2855 Maggs, 1988, Drug-Protein conjugates. XVI. Studies of sorbinil metabolism; formation of 2-hydroxysorbinil and unstable protein conjugates, Biochem. Pharmacol., 37, 743, 10.1016/0006-2952(88)90149-9 Sillanaukee, 1996, Structural characterization of acetaldehyde adducts formed by a synthetic peptide mimicking the N-terminus of hemoglobin β-chain under reducing and nonreducing conditions, Eur. J. Biochem., 240, 30, 10.1111/j.1432-1033.1996.0030h.x Dean, 1984, Enhancement of acetaldehyde-protein adduct formation by L-ascorbate, Arch. Biochem. Biophys., 234, 377, 10.1016/0003-9861(84)90283-2 Fowles, 1996, The formation and stability of imidazolidinone adducts from acetaldehyde and model peptides. A kinetic study with implications for protein modification in alcohol abuse, Biochem. Pharmacol., 51, 1259, 10.1016/0006-2952(95)02408-5 Lash, 1991, Cytotoxicity of alkylating agents in isolated rat kidney proximal tubular and distal tubular cells, Arch. Biochem. Biophys., 286, 46, 10.1016/0003-9861(91)90007-6 Thompson, 1999, Quantification in patient urine samples of felbamate and three metabolites: acid carbamate and two mercapturic acids, Epilepsia, 40, 769, 10.1111/j.1528-1157.1999.tb00777.x Laurent, 2000, Metabolism of 4-hydroxynonenal a cytotoxic product of lipid peroxidation in rat precision cut liver slices, Toxicol. Lett., 114, 203, 10.1016/S0378-4274(99)00301-X Perkins, 1999, Probability-based protein identification by searching sequence databases using mass spectrometry data, Electrophoresis, 20, 3551, 10.1002/(SICI)1522-2683(19991201)20:18<3551::AID-ELPS3551>3.0.CO;2-2 Hurley, 1990, Expression and kinetic characterization of variants of human β1β1 alcohol dehydrogenase containing substitutions at amino acid 47, J. Biol. Chem., 265, 16366, 10.1016/S0021-9258(17)46232-6 Zoranzo, 1990, Differences in kinetic characteristics and in sensitivity to inhibitors between human and rat liver alcohol dehydrogenase and aldehyde dehydrogenase, Gen. Pharmacol., 21, 697, 10.1016/0306-3623(90)91020-R Mori, 1989, Metabolism of 2,4-dinitrotoluene and 2,6-dinitrotoluene and their dinitrobenzyl alcohols and dinitrobenzaldehydes by Wistar and Sprague-Dawley rat liver microsomal and cytosolic fractions, Chem. Pharm. Bull., 37, 1904, 10.1248/cpb.37.1904 Aasmoe, 1998, The role of liver alcohol dehydrogenase isozymes in the oxidation of glycol ethers in male and female rats, Toxicol. Appl. Pharmacol., 150, 86, 10.1006/taap.1998.8410 Olson, 1996, Mechanism of aldehyde oxidation catalysed by horse liver alcohol dehydrogenase, Biochemistry, 35, 9782, 10.1021/bi952020x Svensson, 1996, Aldehyde dismutase activity of human liver alcohol dehydrogenase, FEBS Lett., 394, 217, 10.1016/0014-5793(96)00954-4 Jornvall, 2000, Pharmacogenetics of the alcohol dehydrogenase system, Pharmacology, 61, 184, 10.1159/000028399 Bosron, 1987, Catalytic properties of human liver alcohol dehydrogenase isoenzymes, Enzyme, 37, 19, 10.1159/000469238 Dudley, 2000, Oxidation of thiodiglycol (2,2’-thiobis-ethanol) by alcohol dehydrogenase: comparison of human isoenzymes, J. Biochem. Mol. Tox., 14, 244, 10.1002/1099-0461(2000)14:5<244::AID-JBT3>3.0.CO;2-4 Svensson, 1999, Activities of human alcohol dehydrogenases in the metabolic pathways of ethanol and serotonin, Eur. J. Biochem., 262, 324, 10.1046/j.1432-1327.1999.00351.x Kassam, 1989, In vitro studies of human liver alcohol dehydrogenase varients using a variety of substrates, Drug Metab. Dispos., 17, 567 McEvilly, 1988, 3β-Hydroxy-5β-steroid dehydrogenase activity of human liver alcohol dehydrogenase is specific to γ-subunits, Biochemistry, 27, 4284, 10.1021/bi00412a013 Marschall, 2000, Human liver class I alcohol dehydrogenase γγ isozyme: The sole cytosolic 3β-hydroxysteroid dehydrogenase of iso bile acids, Hepatology, 31, 990, 10.1053/he.2000.5720 Knutson, 1982, Formation and isolation of Δ5-3-ketosteroids using a purified rat liver alcohol dehydrogenase, Steroids, 40, 592, 10.1016/0039-128X(82)90079-4 Kautiainen, 1992, Determination of hemoglobin adducts from aldehydes formed during lipid peroxidation in vitro, Chem-Biol. Interactions, 84, 55, 10.1016/0009-2797(92)90091-X Pohl, 1993, An immunochemical approach of identifying and characterizing protein targets of toxic reactive metabolites, Chem. Res. Toxicol., 6, 786, 10.1021/tx00036a006 Cribb, 1996, Covalent binding of Sulfamethoxazole reactive metabolites to human and rat liver subcellular fractions assessed by immunochemical detection, Chem. Res. Toxicol., 9, 500, 10.1021/tx950167j Hoog, 1986, The γ1 and γ2 subunits of human liver alcohol dehydrogenase. cDNA structures, two amino acid replacements, and compatability with changes in the enzymatic properties, Eur. J. Biochem., 159, 215, 10.1111/j.1432-1033.1986.tb09855.x Van Regenmortel, 2000, Binding measurements as surrogate biological assays: surface plasmon resonance biosensors for characterizing vaccine components, Devel. Biol., 103, 69