Major cytochrome P450 enzyme responsible for oxidation of secondary alcohols to the corresponding ketones in mouse hepatic microsomes: Oxidation of 7-hydroxy-Δ8-tetrahydrocannabinol to 7-oxo-Δ8-tetrahydrocannabinol

Drug Metabolism and Disposition

Volumn 26, Issue 10, 1998, Pages 1045-1047

  Matsunaga, Tamihide ^b   Kishi, Nobuyuki ^b   Tanaka, Hiroyuki ^b   Watanabe, Kazuhito ^b   Yoshimura, Hidetoshi ^b   Yamamoto, Ikuo ^a  

^a HOKURIKU UNIVERSITY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLCHOLANTHRENE; 7 HYDROXY DELTA8 TETRAHYDROCANNABINOLIC ACID; ACETONE; CYTOCHROME P450; DELTA8 TETRAHYDROCANNABINOL DERIVATIVE; DEXAMETHASONE; DRUG METABOLITE; PHENOBARBITAL; POLYCLONAL ANTIBODY; TESTOSTERONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; DRUG OXIDATION; DRUG TRANSFORMATION; ENZYME ACTIVITY; ENZYME PURIFICATION; INTRAPERITONEAL DRUG ADMINISTRATION; LIVER METABOLISM; LIVER MICROSOME; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ALCOHOLS; ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; KETONES; MALE; MICE; MICROSOMES, LIVER; OXIDATION-REDUCTION; TETRAHYDROCANNABINOL;

ANIMALIA;

EID: 0031752988     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Bornheim LM and Correia MA (1991) Purification and characterization of the major hepatic cannabinoid hydroxylase in the mouse: A possible member of the cytochrome P-450IIC subfamily. Mol Pharmacol 40:228-234.
2. Corcos L (1992) Phenobarbital and dexamethasone induce expression of cytochrome P-450 genes from subfamilies IIB, IIC, and IIIA in mouse liver. Drug Metab Dispos 20:797-801.
3. 8-tetrahydrocannabinol: Identification and synthesis. Science 168:844-845.
4. Freeman JE, Stirling D, Russell AL and Wolf CR (1992) cDNA sequence, deduced amino acid sequence, predicted gene structure and chemical regulation of mouse Cyp2e1. Biochem J 281:689-695.
5. Funae Y and Imaoka S (1985) Simultaneous purification of multiple forms of rat liver microsomal cytochrome P-450 by high-performance liquid chromatography. Biochim Biophys Acta 842:119-132.
6. Halvorson M, Greenway D, Eberhart D, Fitzgerald K and Parkinson A (1990) Reconstitution of testosterone oxidation by purified rat cytochrome P450p (IIIA1). Arch Biochem Biophys 277:166-180.
7. Harvey DJ and Paton WDM (1984) Metabolism of the cannabinoids. Rev Biomed Toxicol 6:211-264.
8. Kageura E and Toki S (1974) Guinea pig liver 3-hydroxyhexobarbital dehydrogenase as a 17β-hydroxysteroid dehydrogenase. Biochim Biophys Acta 341:172-177.
9. Kageura E and Toki S (1975) Guinea pig liver 3-hydroxyhexobarbital dehydrogenase: Purification and properties. J Biol Chem 250:5015-5019.
10. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685.
11. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
12. Matsunaga T, Iwawaki Y, Watanabe K, Yamamoto I, Kageyama T and Yoshimura H (1996) Microsomal aldehyde oxygenase (MALDO): Purification and characterization of a cytochrome P450 isozyme responsible for oxidation of 9-anthraldehyde to 9-anthracenecarboxylic acid in monkey liver. J Biochem 119:617-625.
13. 8-tetrahydrocannabinol in guinea pig liver. Arch Biochem Biophys 348:56-64.
14. Mechoulam R, Varconi H, Ben-Zvi Z, Edery H and Grunfeld Y (1972) Synthesis and biological activity of five tetrahydrocannabinol metabolites. J Am Chem Soc 94:7930-7931.
15. Meehan RR, Forrester LM, Stevenson K, Hastie ND, Buchmann A, Kunz HW and Wolf CR (1988) Regulation of phenobarbital-inducible cytochrome P-450s in rat and mouse liver following dexamethasone administration and hypophysectomy. Biochem J 254:789-797.
16. Morgan ET, Koop DR and Coon MJ (1982) Catalytic activity of cytochrome P-450 isozyme 3a isolated from liver microsomes of ethanol-treated rabbits: Oxidation of alcohols. J Biol Chem 257:13951-13957.
17. 8-tetrahydrocannabinol by hepatic microsomes of the guinea pig. Drug Metab Dispos 16:156-161.
18. 8-tetrahydrocannabinol. Res Commun Subst Abuse 5:23-32.
19. Narimatsu S, Watanabe K, Matsunaga T, Yamamoto I, Imaoka S, Funae Y and Yoshimura H (1990) Inhibition of hepatic microsomal cytochrome P450 by cannabidiol in adult male rats. Chem Pharm Bull 38:1365-1368.
20. Nishikawa AH and Bailon P (1975) Affinity purification methods. Improved procedures for cyanogen bromide reaction on agarose. Anal Biochem 64:268-275.
21. 6-tetrahydrocannabinol metabolites. Acta Pharm Suec 16:21-33.
22. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
23. 5 and NADPH-cytochrome c reductase from rat liver microsomes. J Biochem (Tokyo) 67:249-257.
24. Towbin H, Staehelin T and Gordon J (1979) Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: Procedure and some applications. Proc Natl Acad Sci USA 76:4350-4354.
25. 8-tetrahydrocannabinol and its metabolites oxidized at 11-position. Eur J Pharm 63:1-6.
26. 5 in the oxidation of testosterone and nifedipine by recombinant cytochrome P450 3A4 and by human liver microsomes. Arch Biochem Biophys 325:174-182.
27. Yanagimoto T, Itoh S, Muller-Enoch D and Kamataki T (1992) Mouse liver cytochrome P-450 (P-450IIIAM1): Its cDNA cloning and inducibility by dexamethasone. Biochim Biophys Acta 1130:329-332
28. Yasukochi Y and Masters BSS (1976) Some properties of a detergent-solubilized NADPH-cytochrome c (cytochrome P-450) reductase purified by biospecific affinity chromatography. J Biol Chem 251:5337-5344.