Purification and characterization of heterologously expressed mouse CYP2A5 and CYP2G1: Role in metabolic activation of acetaminophen and 2,6- dichlorobenzonitrile in mouse olfactory mucosal microsomes

Journal of Pharmacology and Experimental Therapeutics

Volumn 285, Issue 3, 1998, Pages 1287-1295

  Gu, Jun ^a   Zhang, Qing Yu ^a   Genter, Mary Beth ^b   Lipinskas, Thomas W ^a   Negishi, Masahiko ^c   Nebert, Daniel W ^b   Ding, Xinxin ^a,d  

^a WADSWORTH CENTER   (United States)

^b UNIVERSITY OF CINCINNATI MEDICAL CENTER   (United States)

^c NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^d STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYPARACETAMOL; BERGAPTEN; CYTOCHROME P450 ISOENZYME; DICHLOBENIL; DRUG METABOLITE; ENZYME ANTIBODY; GLUTATHIONE; METHOXSALEN; PARACETAMOL; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; ENZYME ANALYSIS; ENZYME PURIFICATION; LIVER MICROSOME; MALE; METABOLIC ACTIVATION; MICROSOME; MOUSE; NONHUMAN; OLFACTORY EPITHELIUM; PRIORITY JOURNAL; PROTEIN EXPRESSION; TOXICOKINETICS;

ACETAMINOPHEN; ANALGESICS, NON-NARCOTIC; ANIMALS; ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 ENZYME SYSTEM; FEMALE; MICE; MICROSOMES; MIXED FUNCTION OXYGENASES; NITRILES; OLFACTORY MUCOSA; RABBITS; STEROID HYDROXYLASES;

EID: 0031862390     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. Bonnefoi M, Monticello TM and Morgan KT (1991) Toxic and neoplastic responses in the nasal passages: Future research needs. Exp Lung Res 17:853-868.
2. Brandt I, Brittebo EB, Feil VJ and Bakke JE (1990) Irreversible binding and toxicity of the herbicide dichlobenil (2,6-dichlorobenzonitrile) in the olfactory mucosa of mice. Toxicol Appl Pharmacol 103:491-501.
3. Brittebo EB (1993) Metabolism of xenobiotics in the nasal olfactory mucosa: implications for local toxicity. Pharmacol Toxicol 72, Suppl 3:50-52.
4. Camus AM, Geneste O, Honkakoski P, Bereziat JC, Henderson CJ, Wolf CR, Bartsch H and Lang MA (1993) High variability of nitrosamine metabolism among individuals: Role of cytochromes P450 2A6 and 2E1 in the dealkylation of N-nitrosodimethylamine and N-nitrosodiethylamine in mice and humans. Mol Carcinog 7:268-275.
5. Coon MJ, van der Hoeven TA, Dahl SB and Haugen DA (1978) Two forms of liver microsomal cytochrome P-450, P-450LM2 and P-450LM4 (rabbit liver). Methods Enzymol 52:109-117.
6. Dahl AR and Hadley WM (1991) Nasal cavity enzymes involved in xenobiotic metabolism: Effects on the toxicity of inhalants. CRC Crit Rev Toxicol 21:345-372.
7. Dahlin DC and Nelson SD (1982) Synthesis, decomposition kinetics, and preliminary texicological studies of pure N-acetyl-p-benzoquinone imine, a proposed toxic metabolite of acetaminophen. J Med Chem 25:885-886.
8. Deamer NJ, O'Callaghan JP and Genter MB (1994) Olfactory toxicity resulting from dermal application of 2,6-dichlorobenzonitrile (dichlobenil) in the C57Bl mouse. Neurotoxicology 15:287-293.
9. Ding X and Coon MJ (1994) Steroid metabolism by rabbit olfactory-specific P450 2G1. Arch Biochem Biophys 315:454-459.
10. Ding X, Spink DC, Bhama JK, Sheng JJ, Vaz AD and Coon MJ (1996) Metabolic activation of 2,6-dichlorobenzonitrile, an olfactory-specific toxicant, by rat, rabbit, and human cytochromes P450. Mol Pharmacol 49:1113-1121.
11. Ding X and Coon MJ (1988) Purification and characterization of two unique forms of cvtochrome P-450 from rabbit nasal microsomes. Biochemistry 27:8330-8337.
12. Ding X and Coon MJ (1990) Immunochemical characterization of multiple forms of cytochrome P-450 in rabbit nasal microsomes and evidence for tissue-specific expression of P-450s NMa and NMb. Mol Pharmacol 37:489-496.
13. Ding X, Pernecky SJ and Coon MJ (1991) Purification and characterization of cytochrome P450 2E2 from hepatic microsomes of neonatal rabbits. Arch Biochem Biophys 291:270-276.
14. Eriksson C and Brittebo EB (1995) Metabolic activation of the olfactory toxicant, dichlobenil, in rat olfactory microsomes: Comparative studies with p-nitrophenol. Chem Biol Interact 94:183-196.
15. Genter MB, Llorens J, O'Callaghan JP, Peele DB, Morgan KT and Crofton KM (1992) Olfactory toxicity of β,β′-iminodipropionitrile in the rat. J Pharmacol Exp Ther 263:1432-1439.
16. Genter MB, Liang HC, Gu J, Ding X, Negishi M, McKinnon RA and Nebert DW (1998) Role of CYP2A5 and CYP2G1 in acetaminophen metabolism and toxicity in the olfactory mucosa of Cyp1a2(-/-) mouse. Biochem Pharmacol In press.
17. Gu J, Walker VE, Lipinskas TW, Walker DM and Ding X (1997) Intraperitoneal administration of coumarin causes tissue-selective depletion of cytochromes P450 and cytotoxicity of the olfactory mucosa. Toxicol Appl Pharmacol 146:134-143.
18. Harvison PJ, Guengerich FP, Rashed MS and Nelson SD (1988) Cytochrome P-450 isozyme selectivity in the oxidation of acetaminophen. Chem Res Toxicol 1:47-52.
19. Hinson JA, Pohl LR, Monks TJ, Gillette JR and Guengerich FP (1980) 3-Hydroxy-acetaminophen: A microsomal metabolite of acetaminophen: Evidence against an epoxide as the reactive metabolite of acetaminophen. Drug Metab Dispos 8:289-294.
20. Hua Z, Zhang QY, Su T, Lipinskas TW and Ding X (1997) cDNA cloning, heterologous expression, and characterization of mouse CYP2G1, an olfactory-specific steroid hydroxylase. Arch Biochem Biophys 340:208-214.
21. Jeffery EH and Haschek WM (1988) Protection by dimethylsulfoxide against acetaminophen-induced hepatic, but not respiratory toxicity in the mouse. Toxicol Appl Pharmacol 93:452-461.
22. Kostrubsky VE, Szakacs JG, Jeffery EH, Wood SG, Bernent WJ, Wrighton SA, Sinclair PR and Sinclair JF (1997) Role of CYP3A in ethanol-mediated increases in acetaminophen hepatotoxicity. Toxicol Appl Pharmacol 143:315-323.
23. Lee ST, Buters JM, Pineau T, Fernandezsalguero P and Gonzalez FJ (1996) Role of CYP2E1 in the hepatotoxicity of acetaminophen. J Biol Chem 271:12063-12067.
24. Liang HL, Li H, Mckinnon RA, Duffy JJ, Potter SS, Puga A and Nebert DW (1996) Cyp1a2(-/-) null mutant mice develop normally but show deficient drug metabolism. Proc Natl Acad Sci USA 93:1671-1676.
25. Liu C, Zhuo X, Gonzalez FJ and Ding X (1996) Baculovirus-mediated expression and characterization of rat CYP2A3 and human CYP2a6: Role in metabolic activation of nasal toxicants. Mol Pharmacol 50:781-788.
26. Maenpaa J, Sigusch H, Raunio H, Syngelma T, Vuorela P, Vuorela H and Pelkonen O (1993) Differential inhibition of coumarin 7-hydroxylase activity in mouse and human liver microsomes. Biochem Pharmacol 45:1035-1042.
27. McKinney MM and Parkinson A (1987) A simple, non-chromatographic procedure to purify immunoglobulins from serum and ascites fluid. J Immunol Methods 96: 271-278.
28. Morgan ET, Koop DR and Coon MJ (1983) Comparison of six rabbit liver cytochrome P-450 isozymes in formation of a reactive metabolite of acetaminophen. Biochem Biophya Res Commun 112:8-13.
29. Negishi M, Lindberg R, Burkhart B, Ichikawa T, Honkakoski P and Lang M (1989) Mouse steroid 15 alpha-hydroxylase gene family: Identification of type II P-450(15)alpha as coumarin 7-hydroxylase. Biochemistry 28:4169-4172.
30. Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, Gunsalus IC and Nebert DW (1996) P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6:1-42.
31. Omura T and Sato R (1964) The carbon monoxide-binding protein of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
32. Park SS, Waxman DJ, Miller H, Robinson R, Attisano C, Guengerich FP and Gelboin HV (1986) Preparation and characterization of monoclonal antibodies to pregnenolone 16-alpha-carbonitrile inducible rat liver cytochrome P-450. Biochem Pharmacol 35:2859-2867.
33. Patten CJ, Thomas PE, Guy RL, Lee M, Gonzalez FJ, Guengerich FP and Yang CS (1993) Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. Chem Res Toxicol 6:511-518.
34. Pelkonen P, Lang MA, Wild CP, Negishi M and Juvonen RO (1994) Activation of aflatoxin B1 by mouse CYP2A enzymes and cytotoxicity in recombinant yeast cells. Eur J Pharmacol 292:67-73.
35. Peng HM, Ding X and Coon MJ (1993) Isolation and heterologous expression of cloned cDNAs for two rabbit nasal microsomal proteins, CYP2A10 and CYP2A11, that are related to nasal microsomal cytochrome P450 form a. J Biol Chem 268:17253-17260.
36. Placke ME, Wyand DS and Cohen SD (1987) Extrahepatic lesions induced by acetaminophen in the mouse. Toxicol Pathol 15:381-387.
37. Su T, Sheng JJ, Lipinskas TW and Ding X (1996) Expression of CYP2A genes in rodent and human nasal mucosa. Drug Metab Dispos 24:884-890.
38. Sueyoshi T, Park LJ, Moore R, Juvonen RO and Negishi M (1995) Molecular engineering of microsomal P450 2a-4 to a stable, water-soluble enzyme. Arch Biochem Biophys 322:265-271.
39. Walters E, Buchheit K and Maruniak JA (1993) Olfactory cytochrome P-450 immunoreactivity in mice is altered by dichlobenil but preserved by metyrapone. Toxicology 81:113-122.
40. Zhou LX, Erickson RR, Hardwick JP, Park SS, Wrighton SA and Holtzman JL (1997) Catalysis of the cysteine conjugation and protein binding of acetaminophen by microsomes from a human lymphoblast line transfected with the cDNAs of various forms of human cytochrome P450. J Pharmacol Exp Ther 281:785-790.