Chlorzoxazone metabolism by porcine cytochrome P450 enzymes and the effect of cytochrome b5

Drug Metabolism and Disposition

Volumn 38, Issue 5, 2010, Pages 857-862

  Wiercinska, P ^a   Squires, E J ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORZOXAZONE; COMPLEMENTARY DNA; CYTOCHROME B5; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 2E1; PROTEIN;

ARTICLE; CELL LINE; CONTROLLED STUDY; EMBRYO; ENZYME ACTIVITY; HUMAN; HUMAN CELL; HYDROXYLATION; IN VIVO STUDY; LIVER; LIVER CELL; MICROSOME; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL;

ANIMALS; ARYL HYDROCARBON HYDROXYLASES; BIOCATALYSIS; CELL LINE; CHLORZOXAZONE; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP2E1; CYTOCHROME P-450 ENZYME SYSTEM; CYTOCHROMES B5; HUMANS; HYDROXYLATION; KINETICS; STEROID HYDROXYLASES; SUS SCROFA; TRANSFECTION;

SUIDAE; SUS;

EID: 77950960669     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.030528     Document Type: Article

References (39)

1. Abdel-Razzak Z, Loyer P, Fautrel A, Gautier JC, Corcos L, Turlin B, Beaune P, and Guillouzo A (1993) Cytokines down-regulate expression of major cytochrome P-450 enzymes in adult human hepatocytes in primary culture. Mol Pharmacol 44:707-715. (Pubitemid 23317282)
2. Anzenbacherová E, Baranová J, Zuber R, Pechová A, Anzenbacher P, Soucek P, and Martínková J (2005) Model systems based on experimental animals for studies on drug metabolism in man: (mini)pig cytochromes P450 3A29 and 2E1. Basic Clin Pharmacol Toxicol 96:244-245.
3. Balk MW (1987) Emerging models in the USA: swine, woodchucks and the hairless guinea pig, in Animal Models: Assessing the Scope of Their Use in Biomedical Research (Kawamata J and Melby EC eds) pp 311-326, Alan R. Liss, New York.
4. Baranová J, Anzenbacherová E, Anzenbacher P, and Soucek P (2005) Minipig cytochrome P450 2E1: comparison with human enzyme. Drug Metab Dispos 33:862-865. (Pubitemid 40686641)
5. Bertz RJ and Granneman GR (1997) Use of in vitro and in vivo data to estimate the likelihood of metabolic pharmacokinetic interactions. Clin Pharmacokinet 32:210-258.
6. Billen MJ and Squires EJ (2009) The role of porcine cytochrome b5A and cytochrome b5B in the regulation of cytochrome P45017A1 activities. J Steroid Biochem Mol Biol 113:98-104.
7. Bogaards JJ, Bertrand M, Jackson P, Oudshoorn MJ, Weaver RJ, van Bladeren PJ, and Walther B (2000) Determining the best animal model for human cytochrome P450 activities: a comparison of mouse, rat, rabbit, dog, micropig, monkey and man. Xenobiotica 30:1131-1152. (Pubitemid 32368013)
8. Carriere V, Goasduff T, Ratanasavanh D, Morel F, Gautier JC, Guillouzo A, Beaune P, and Berthou F (1993) Both cytochromes P450 2E1 and 1A1 are involved in the metabolism of chlorzoxazone. Chem Res Toxicol 6:852-857. (Pubitemid 23351209)
9. Court HM, Von Moltke LL, Shader IR, and Greenblatt JD (1997) Biotransformation of CLZ by hepatic microsomes from humans and ten other mammalian species. Biopharm Drug Dispos 18; 213-226.
10. 5 in the bioactivation activities of human CYP1A2, 2A6 and 2E1: a new cell expression system to study cytochrome P450-mediated biotransformation (a corrigendum report on Duarte et al. (2005) Mutagenesis 20, 93-100). Mutagenesis 22:75-81.
11. Emery MG, Fisher JM, Chien JY, Kharasch ED, Dellinger EP, Kowdley KV, and Thummel KE (2003) CYP2E1 activity before and after weight loss in morbidly obese subjects with nonalcoholic fatty liver disease. Hepatology 38:428-435.
12. Ernstgård L, Warholm M, and Johanson G (2004) Robustness of chlorzoxazone as an in vivo measure of cytochrome P450 2E1 activity. Br J Clin Pharmacol 58:190-200. (Pubitemid 39044000)
13. Friis C (1995) Is boar taint related to sex differences or polymorphism of skatole metabolism. Proceedings of the EAAP Working Group on Production and Utilization of Meat from Entire Male Pigs; 1995 Sept 27-29; Milton Keynes, UK. Meat and Livestock Commission, Milton Keynes, UK; INRA, Paris, France.
14. Gillam EM, Guo Z, and Guengerich FP (1994) Expression of modified human cytochrome P450 2E1 in Escherichia coli, purification, and spectral and catalytic properties. Arch Biochem Biophys 312:59-66. (Pubitemid 24243799)
15. Gorski JC, Jones DR, Wrighton SA, and Hall SD (1997) Contribution of human CYP3A subfamily members to the 6-hydroxylation of chlorzoxazone. Xenobiotica 27:243-256.
16. Handley-Gearhart PM, Stephen AG, Trausch-Azar JS, Ciechanover A, and Schwartz AL (1994) Human ubiquitin-activating enzyme, E1. Indication of potential nuclear and cytoplasmic subpopulations using epitope-tagged cDNA constructs. J Biol Chem 269:33171-33178.
17. Ingelman-Sundberg M (2004) Human drug metabolising cytochrome P450 enzymes: properties and polymorphisms. Naunyn Schmiedebergs Arch Pharmacol 369:89-104. (Pubitemid 38161226)
18. Juskevich JC (1987) Comparative metabolism in food-producing animals: programs sponsored by the Center for Veterinary Medicine. Drug Metab Rev 18:345-362.
19. Kojima M and Morozumi T (2004) Cloning of six full length cDNAs encoding pig cytochrome P450 enzymes and gene expression of these enzymes in the liver and kidney. J Health Sci 50:518-529. (Pubitemid 41295297)
20. Lejus C, Fautrel A, Mallédant Y, and Guillouzo A (2002) Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol 64:1151-1156. (Pubitemid 35247823)
21. Lieber CS (1997) Cytochrome P-4502E1: its physiological and pathological role. Physiol Rev 77:517-544.
22. Madan A, Usuki E, Burton LA, Ogilvie WB, and Parkinson A. (2002) In vitro approaches for studying the inhibition of drug-metabolizing enzymes and identifying the drug-metabolizing enzymes responsible for the metabolism of drugs, in Drugs and The Pharmaceutical Sciences: Drug-Drug Interactions (Rodrigues AD ed) pp 217-294, Marcel Dekker, New York.
23. Masimirembwa CM, Otter C, Berg M, Jönsson M, Leidvik B, Jonsson E, Johansson T, Bäckman A, Edlund A, and Andersson TB (1999) Heterologous expression and kinetic characterization of human cytochromes P-450: validation of a pharmaceutical tool for drug metabolism research. Drug Metab Dispos 27:1117-1122.
24. Monshouwer M, van't Klooster GA, Nijmeijer SM, Witkamp RF, and van Miert AS (1998) Characterization of cytochrome P450 isoenzymes in primary cultures of pig hepatocytes. Toxicol In Vitro 12:715-723.
25. Myers MJ, Farrell DE, Howard KD, and Kawalek JC (2001) Identification of multiple constitutive and inducible hepatic cytochrome P450 enzymes in market weight swine. Drug Metab Dispos 29:908-915.
26. Overton CL, Hudder A, and Novak FR (2008) The CYP2E subfamily, in Cytochrome P450: Role in the Metabolism and Toxicity of Drugs and Other Xenobiotics (Ioannides C ed) pp 276-308, Royal Society of Chemistry, Cambridge, UK.
27. Peng HM and Coon MJ (1998) Regulation of rabbit cytochrome P450 2E1 expression in HepG2 cells by insulin and thyroid hormone. Mol Pharmacol 54:740-747.
28. Peter R, Böcker R, Beaune PH, Iwasaki M, Guengerich FP, and Yang CS (1990) Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem Res Toxicol 3:566-573.
29. Raucy JL, Kraner JC, and Lasker JM (1993) Bioactivation of halogenated hydrocarbons by cytochrome P4502E1. Crit Rev Toxicol 23:1-20.
30. Rendic S and Di Carlo FJ (1997) Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab Rev 29:413-580.
31. Schenkman JB and Jansson I (2003) The many roles of cytochrome b5. Pharmacol Ther 97:139-152.
32. Skaanild MT and Friis C (2007) Is bupropion a more specific substrate for porcine CYP2E than chlorzoxazone and p-nitrophenol? Basic Clin Pharmacol Toxicol 101:159-162.
33. Szotáková B, Baliharová V, Lamka J, Nozinová E, Wsól V, Velík J, Machala M, Neca J, Soucek P, Susová S, et al. (2004) Comparison of in vitro activities of biotransformation enzymes in pig, cattle, goat and sheep. Res Vet Sci 76:43-51.
34. Tan Y, Patten CJ, Smith T, and Yang CS (1997) Competitive interactions between cytochromes P450 2A6 and 2E1 for NADPH-cytochrome P450 oxidoreductase in the microsomal membranes produced by a baculovirus expression system. Arch Biochem Biophys 342:82-91.
35. Tsiaoussis J, Newsome PN, Nelson LJ, Hayes PC, and Plevris JN (2001) Which hepatocyte will it be? Hepatocyte choice for bioartificial liver support systems. Liver Transpl 7:2-10.
36. Waxman DJ, Morrissey JJ, and LeBlanc GA (1989) Female-predominant rat hepatic P-450 forms j (IIE1) and 3 (IIA1) are under hormonal regulatory controls distinct from those of the sex-specific P-450 forms. Endocrinology 124:2954-2966.
37. Yamazaki H, Guo Z, and Guengerich FP (1995) Selectivity of cytochrome P4502E1 in chlorzoxazone 6-hydroxylation. Drug Metab Dispos 23:438-440.
38. Yamazaki H, Nakamura M, Komatsu T, Ohyama K, Hatanaka N, Asahi S, Shimada N, Guengerich FP, Shimada T, Nakajima M, et al. (2002) Roles of NADPH-P450 reductase and apo- and holo-cytochrome b5 on xenobiotic oxidations catalyzed by 12 recombinant human cytochrome P450s expressed in membranes of Escherichia coli. Protein Expr Purif 24:329-337.
39. 5 in the oxidation of 7-ethoxycoumarin, chlorzoxazone, aniline, and N-nitrosodimethylamine by recombinant cytochrome P450 2E1 and by human liver microsomes. Biochem Pharmacol 52:301-309.