Epoxidation of C18 unsaturated fatty acids by cytochromes P4502C2 and P4502CAA

Drug Metabolism and Disposition

Volumn 24, Issue 6, 1996, Pages 664-668

  Laethem, Ronald M ^a,c   Balazy, Michael ^b   Koop, Dennis R ^a  

^a OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

^b NEW YORK MEDICAL COLLEGE   (United States)

^c GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONIC ACID; CYTOCHROME P450 ISOENZYME; DRUG METABOLITE; EPOXIDE; GAMMA LINOLENIC ACID; LINOLEIC ACID; LINOLENIC ACID; OLEIC ACID; TRICHLOROPROPYLENE OXIDE; UNSATURATED FATTY ACID; ARACHIDONATE EPOXYGENASE; CYTOCHROME P 450 2C2; CYTOCHROME P-450 2C2; CYTOCHROME P450; OXYGENASE;

ANIMAL CELL; ARTICLE; CELL STRAIN COS1; CONTROLLED STUDY; DRUG STRUCTURE; EPOXIDATION; FATTY ACID METABOLISM; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; ANIMAL; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; HUMAN; LIVER MICROSOME; METABOLISM; METHODOLOGY; RABBIT;

ANIMALS; ARACHIDONIC ACID; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; FATTY ACIDS, UNSATURATED; HUMANS; MICROSOMES, LIVER; OXYGENASES; RABBITS;

EID: 0029659002     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. D. R. Nelson, T. Kamatika, D. J. Waxman, F. P. Guengerich, R. W. Estabrook, R. Feyereisen, F. J. Gonzalez, M. J. Coon, I. C. Gunsalus, O. Gotoh, K. Okuda, and D. W. Nebert: The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA Cell Biol. 12, 1-51 (1993).
2. T. D. Porter and M. J. Coon: Cytochrome P-450. Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J. Biol. Chem. 266, 13469-13472 (1991).
3. D. W. Nebert: Drug-metabolizing enzymes in ligand-modulated transcription. Biochem. Pharmacol. 47, 25-37 (1994).
4. F. A. Fitzpatrick and R. C. Murphy: Cytochrome P450 metabolism of arachidonic acid: formation and biological actions of "epoxygenase"-derived eicosanoids. Pharmacol. Rev. 40, 229-241 (1989).
5. J. H. Capdevila, J. R. Falck, and R. W. Estabrook: Cytochrome P450 and the arachidonate cascade. FASEB J. 6, 731-736 (1992).
6. T. Fukuda, Y. Imai, M. Komori, M. Nakamura, E. Kusunose, K. Satouchi, and M. Kusunose: Different mechanisms of regioselection of fatty acid hydroxylation by laurate (ω-1)-hydroxylating P450s, P450 2C2 and P450 2E1. J. Biochem. 115, 338-344 (1994).
7. R. M. Laethem and D. R. Koop: Identification of rabbit cytochromes P450 2C1 and 2C2 as arachidonic acid epoxygenases. Mol. Pharmacol. 42, 958-963 (1992).
8. J. H. Capdevila, A. Karara, D. J. Waxman, M. V. Martin, J. R. Falck, and F. P. Guengerich: Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase. J. Biol. Chem. 265, 10865-10871 (1990).
9. S. Imaoka, P. J. Wedlund, H. Ogawa, S. Kimura, F. J. Gonzalez, and H.-Y. Kim: Identification of CYP2C23 expressed in rat kidney as an arachidonic acid epoxygenase. J. Pharmacol. Exp. Ther. 267, 1012-1016 (1993).
10. A. Karara, K. Makita, H. R. Jacobson, J. R. Falck, F. P. Guengerich, R. N. DuBois, and J. H. Capdevila: Molecular cloning, expression, and enzymatic characterization of the rat kidney cytochrome P450 arachidonic acid epoxygenase. J. Biol. Chem. 268, 13565-13570 (1993).
11. B. E. Daikh, J. M. Lasker, J. L. Raucy, and D. R. Koop: Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9. J. Pharmacol. Exp. Ther. 271, 1427-1433 (1994).
12. A. B. Rifkind, C. Lee, T. K. H. Chang, and D. J. Waxman: Arachidonic acid metabolism by human Cytochrome P450s 2C8, 2C9, 2E1, and 1A2: regioselective oxygenation and evidence for a role for CYP2C enzymes in arachidonic acid epoxygenation in human liver microsomes. Arch. Biochem. Biophys. 320, 380-389 (1995).
13. R. M. Laethem, C. L. Laethem, and D. R. Koop: Purification and properties of a cytochrome P450 arachidonic acid epoxygenase from rabbit renal cortex. J. Biol. Chem. 267, 5552-5559 (1992).
14. S.-K. Chung, and A. I. Scott: Synthesis of (±)eicosa-cis-8,9-(11,12- and 14,15-) epoxy-cis-11,14-(8,14- and 8,11-) dienoic acids and attempted bioconversion to prostaglandins. Tetrahedron Lett. 35, 3023-3024 (1974).
15. M. Balazy: Metabolism of 5,6-epoxyeicosatrienoic acid by the human platelet. J. Biol. Chem. 266, 23561-23567 (1991).
16. B. L. Clark and M. R. Waterman: Heterologous expression of mammalian P450 in COS cells. Methods Enzymol. 206, 100-108 (1991).
17. O. H. Lowry, N. J. Rosebrough, A. L. Farr, and R. J. Randall: Protein measurement with the Polin phenol reagent. J. Biol. Chem. 193, 265-275 (1951).
18. J. S. French and M. J. Coon: Properties of NADPH-cytochrome P-450 reductase purified from rabbit liver microsomes. Arch. Biochem. Biophys. 195, 565-577 (1979).
19. D. R. Dutton, S. K. McMillen, A. J. Sonderfan, P. E. Thomas, and A. Parkinson: Studies in the rate-determining factor in testosterone hydroxylation by rat liver microsomal cytochrome P450: evidence against cytochrome P450 isozyme:isozyme interactions. Arch. Biochem. Biophys. 255, 316-328 (1987).
20. A. H. Phillips and R. G. Langdon: Hepatic triphosphopyridine nucleotide-cytochrome c reductase isolation, characterization, and kinetic studies. J. Biol. Chem. 237, 2652-2660 (1962).
21. 5. Methods Ezymol. 52, 97-101 (1978).
22. R. M. Laethem, J. R. Halpert, and D. R. Koop: Epoxidation of arachidonic acid as an active-site probe of cytochrome P450 isoforms. Biochim. Biophys. Acta. 1206, 42-48 (1994).
23. B. E. Daikh, R. M. Laethem, and D. R. Koop: Stereoselective epoxidation of arachidonic acid by cytochrome P450s 2CAA and 2C2. J. Pharmacol. Exp. Ther. 269, 1130-1135 (1994).
24. J. R. Falck, S. Lumin, I. Blair, E. Dishman, M. V. Martin, D. J. Waxman, F. P. Guengerich, and J. H. Capdevila: Cytochrome P-450-dependent oxidation of arachidonic acid to 16-, 17-, and 18-hydroxyeicosatetraenoic acids. J. Biol. Chem. 265, 10244-10249 (1990).
25. cam. J. Mol. Biol. 195, 687-700 (1987).
26. terp at 2.3 Å resolution. J. Mol. Biol. 236, 1169-1185 (1994).
27. C. A. Hasemann, R. G. Kurumbail, S. S. Boddupalli, J. A. Peterson, and J. Deisenhofer: Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure 2, 41-62 (1995).
28. +-ATPase inhibitors from acute volume-expanded hog plasma. J. Biol. Chem. 260, 9672-9677 (1985).
29. +2 mobilization and protein phosphorylation in human platelets in presence or absence of platelet activating factor, Arch. Biochem. Biophys. 298, 471-479 (1992).
30. R. J. Distel, G. S. Robinson, and B. M. Spiegelman: Fatty acid regulation of gene expression. J. Biol. Chem. 267, 5937-5941 (1992).
31. C. Sumida, R. Graber, and E. Nunez: Role of fatty acids in signal transduction: modulators and messengers. Prostaglandins Leukot. Essent. Fatty Acids 48, 117-122 (1993).
32. H. Mukai, M. Kitagawa, H. Shibata, H. Takanaga, K. Mon, M. Shimakawa, M. Miyahara, K. Hirao, and Y. Ono: Activation of PKN, a novel 120-KDa protein kinase with leucine zipper-like sequences, by unsaturated fatty acids and by limited proteolysis. Biochem. Biophys. Res. Commun. 204, 348-356 (1994).
33. M. Kurokawa, T. Hirano, S. Furukawa, S. Nagano, and M. Adachi: Similar to oleic acid, eicosapentaenoic acid stimulates apolipoprotein B secretion by inhibiting its intracellular degradation in Hep G2 cells. Atherosclerosis 112, 59-68 (1995).