Covalent modification and time-dependent inhibition of human CYP2E1 by the meta-isomer of acetaminophen

Drug Metabolism and Disposition

Volumn 40, Issue 8, 2012, Pages 1460-1465

  Harrelson, John P ^a   Stamper, Brendan D ^b   Chapman, John D ^b   Goodlett, David R ^b   Nelson, Sidney D ^b  

^a PACIFIC UNIVERSITY   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; CYTOCHROME B5; CYTOCHROME P450 2E1; CYTOCHROME P450 REDUCTASE; DRUG METABOLITE; GLUTATHIONE; HEME; HYDROQUINONE; METACETAMOL; QUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; CONCENTRATION (PARAMETERS); CONJUGATION; CONTROLLED STUDY; COVALENT BOND; ENZYME INHIBITION; ENZYME MODIFICATION; HUMAN; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT;

ACETAMINOPHEN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 CYP2E1; HUMANS; ISOMERISM; NADP; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

MUS;

EID: 84863960350     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.045492     Document Type: Article

References (27)

1. Bower WA, Johns M, Margolis HS, Williams IT, and Bell BP (2007) Population-based surveillance for acute liver failure. Am J Gastroenterol 102:2459-2463.
2. Caro AA and Cederbaum AI (2004) Oxidative stress, toxicology, and pharmacology of CYP2E1. Annu Rev Pharmacol Toxicol 44:27-42.
3. Chen W, Shockcor JP, Tonge R, Hunter A, Gartner C, and Nelson SD (1999) Protein and nonprotein cysteinyl thiol modification by N-acetyl-p-benzoquinone imine via a novel ipso adduct. Biochemistry 38:8159-8166.
4. Gotoh O (1992) Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J Biol Chem 267:83-90.
5. Grimm SW, Einolf HJ, Hall SD, He K, Lim HK, Ling KH, Lu C, Nomeir AA, Seibert E, Skordos KW, et al. (2009) The conduct of in vitro studies to address time-dependent inhibition of drug-metabolizing enzymes: a perspective of the pharmaceutical research and manufacturers of America. Drug Metab Dispos 37:1355-1370.
6. Halmes NC, Samokyszyn VM, Hinton TW, Hinson JA, and Pumford NR (1998) The acetaminophen regioisomer 3′-hydroxyacetanilide inhibits and covalently binds to cytochrome P450 2E1. Toxicol Lett 94:65-71.
7. Hinson JA, Roberts DW, and James LP (2010) Mechanisms of acetaminophen-induced liver necrosis. Handb Exp Pharmacol 196:369-405.
8. Lee SS, Buters JT, Pineau T, Fernandez-Salguero P, and Gonzalez FJ (1996) Role of CYP2E1 in the hepatotoxicity of acetaminophen. J Biol Chem 271:12063-12067.
9. Lee WM (2004) Acetaminophen and the U.S. Acute Liver Failure Study Group: lowering the risks of hepatic failure. Hepatology 40:6-9.
10. Lieber CS (2004) The discovery of the microsomal ethanol oxidizing system and its physiologic and pathologic role. Drug Metab Rev 36:511-529.
11. Matthews AM, Hinson JA, Roberts DW, and Pumford NR (1997) Comparison of covalent binding of acetaminophen and the regioisomer 3′- hydroxyacetanilide to mouse liver protein. Toxicol Lett 90:77-82.
12. Nelson EB (1980) The pharmacology and toxicology of meta-substituted acetanilide I: acute toxicity of 3-hydroxyacetanilide in mice. Res Commun Chem Pathol Pharmacol 28:447-456.
13. Porubsky PR, Battaile KP, and Scott EE (2010) Human cytochrome P450 2E1 structures with fatty acid analogs reveal a previously unobserved binding mode. J Biol Chem 285:22282-22290.
14. Porubsky PR, Meneely KM, and Scott EE (2008) Structures of human cytochrome P-450 2E1. Insights into the binding of inhibitors and both small molecular weight and fatty acid substrates. J Biol Chem 283:33698-33707.
15. Qiu Y, Benet LZ, and Burlingame AL (2001) Identification of hepatic protein targets of the reactive metabolites of the non-hepatotoxic regioisomer of acetaminophen, 3′-hydroxyacetanilide, in the mouse in vivo using two-dimensional gel electrophoresis and mass spectrometry. Adv Exp Med Biol 500:663-673.
16. Rashed MS, Myers TG, and Nelson SD (1990) Hepatic protein arylation, glutathione depletion, and metabolite profiles of acetaminophen and a non-hepatotoxic regioisomer, 3′-hydroxyacetanilide, in the mouse. Drug Metab Dispos 18:765-770.
17. Rashed MS and Nelson SD (1989) Characterization of glutathione conjugates of reactive metabolites of 3′-hydroxyacetanilide, a nonhepatotoxic positional isomer of acetaminophen. Chem Res Toxicol 2:41-45.
18. Roberts SA and Jollow DJ (1978) Acetaminophen structure-toxicity relationships: why is 3-hydroxyacetanilide not hepatotoxic. Pharmacologist 20:259.
19. Scott EE, He YA, Wester MR, White MA, Chin CC, Halpert JR, Johnson EF, and Stout CD (2003) An open conformation of mammalian cytochrome P450 2B4 at 1.6-A resolution. Proc Natl Acad Sci USA 100:13196-13201.
20. Shen AL, Porter TD, Wilson TE, and Kasper CB (1989) Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis. J Biol Chem 264:7584-7589.
21. Silverman RB (1988) Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology, CRC Press, Boca Raton, FL.
22. Spracklin DK, Hankins DC, Fisher JM, Thummel KE, and Kharasch ED (1997) Cytochrome P450 2E1 is the principal catalyst of human oxidative halothane metabolism in vitro. J Pharmacol Exp Ther 281:400-411.
23. Stamper BD, Mohar I, Kavanagh TJ, and Nelson SD (2011) Proteomic analysis of acetaminophen-induced changes in mitochondrial protein expression using spectral counting. Chem Res Toxicol 24:549-558.
24. Streeter AJ, Bjorge SM, Axworthy DB, Nelson SD, and Baillie TA (1984) The microsomal metabolism and site of covalent binding to protein of 3′-hydroxyacetanilide, a nonhepatotoxic positional isomer of acetaminophen. Drug Metab Dispos 12:565-576.
25. Tirmenstein MA and Nelson SD (1989) Subcellular binding and effects on calcium homeostasis produced by acetaminophen and a nonhepatotoxic regioisomer, 3′-hydroxyacetanilide, in mouse liver. J Biol Chem 264:9814-9819.
26. Valentine JL, Lee SS, Seaton MJ, Asgharian B, Farris G, Corton JC, Gonzalez FJ, and Medinsky MA (1996) Reduction of benzene metabolism and toxicity in mice that lack CYP2E1 expression. Toxicol Appl Pharmacol 141:205-213.
27. Yamazaki H, Inui Y, Yun CH, Guengerich FP, and Shimada T (1992) Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis 13:1789-1794.