CYP4 isoform specificity in the ω-hydroxylation of phytanic acid, a potential route to elimination of the causative agent of Refsum's disease

Journal of Pharmacology and Experimental Therapeutics

Volumn 318, Issue 2, 2006, Pages 835-839

  Xu, Fengyun ^a   Ng, Valerie Y ^a   Kroetz, Deanna L ^a   Ortiz De Montellano, Paul R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CLOFIBRATE; CYTOCHROME P450 4A; ISOENZYME; PHYTANIC ACID;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME SPECIFICITY; FATTY ACID OXIDATION; HUMAN; HYDROXYLATION; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; REFSUM DISEASE;

ANIMALS; ANTILIPEMIC AGENTS; BLOTTING, WESTERN; CLOFIBRATE; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INDUCTION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; HYDROXYLATION; ISOENZYMES; KINETICS; MALE; MICROSOMES, LIVER; OXIDATION-REDUCTION; PHYTANIC ACID; RATS; RATS, INBRED F344; REFSUM DISEASE; SUBSTRATE SPECIFICITY;

EID: 33745962817     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.106.104976     Document Type: Article

References (27)

1. Alterman MA, Chaurasia CS, Lu P, Hardwick JP, and Hanzlik RP (1995) Fatty acid discrimination and ω-hydroxylation by cytochrome P450 4A1 and a cytochrome P4504A1/NADPH-P450 reductase fusion protein. Arch Biochem Biophys 320:289-296.
2. Bambal RB and Hanzlik RP (1996) Effects of steric bulk and conformational rigidity on fatty acid omega hydroxylation by a cytochrome P450 4A1 fusion protein. Arch Biochem Biophys 334:59-66.
3. Capdevila JH, Holla VR, and Falck JR (2005) Cytochrome P450 and the metabolism and bioactivation of arachidonic acid and eicosanoids, in Cytochrome P450: Structure, Mechanism, and Biochemistry (Ortiz de Montellano PR ed) 3rd ed, pp 531-551, Kluwer/Plenum, New York.
4. Dierks EA, Zhang Z, Johnson EF, and Ortiz de Montellano PR (1998) The catalytic site of cytochrome P4504A11 (CYP4A11) and its L131F mutant. J Biol Chem 273:23055-23061.
5. He X, Cryle MJ, De Voss JJ, and Ortiz de Montellano PR (2005) Calibration of the channel that determines the ω-hydroxylation regiospecificity of cytochrome P450 4A1: catalytic oxidation of 12-halododecanoic acids. J Biol Chem 280:22697-22705.
6. Hoch U, Zhang Z, Kroetz DL, and Ortiz de Montellano PR (2000) Structural determination of the substrate specificities and regioselectivities of the rat and human fatty acid omega-hydroxylases. Arch Biochem Biophys 373:63-71.
7. Holmes VE, Bruce M, Shaw PN, Bell DR, Qi FM, and Barrett DA (2004) A gas chromatography-mass spectrometry method for the measurement of fatty acid omega and omega(-1) hydroxylation kinetics by CYP4A1 using an artificial membrane system. Anal Biochem 325:354-363.
8. Jansen GA, Ofman R, Ferdinandusse S, Ijlst L, Muijsers AO, Skjeldal OH, Stokke O, Jakobs C, Besley GTN, Wraith E, et al. (1997a) Refsum's disease is caused by mutations in the phytanoyl-CoA hydroxylase gene. Nat Genet 17:190-193.
9. Jansen GA, Wanders RJA, Watkins PA, and Mihalik S (1997b) Phytanoyl-coenzyme A hydroxylase deficiency: the enzyme defect in Refsum's disease. N Engl J Med 337:133-134.
10. Komen JC, Duran M, and Wanders RJA (2004) ω-Hydroxylation of phytanic acid in rat liver microsomes: implications for Refsum's disease. J Lipid Res 45:1341-1345.
11. Komen JC, Duran M, and Wanders RJA (2005) Characterization of phytanic acid ω-hydroxylation in human liver microsomes. Mol Genet Metab 85:190-195.
12. Lawrence JW, Li Y, Chen S, DeLuca JG, Berger JP, Umbenhauer DR, Moller DE, and Zhou G (2001) Differential gene regulation in human versus rodent hepatocytes by peroxisome proliferator-activated receptor (PPAR) α. J Biol Chem 276:31521-31527.
13. Mihalik SJ, Morrell JC, Kim D, Sacksteder KA, Watkins PA, and Gould SJ (1997) Identification of PAHX, a Refsum disease gene. Nature (Lond) Genet 17:185-189.
14. Okita RT and Okita JR (2001) Cytochrome P450 4A fatty acid omega hydroxylases. Curr Drug Metab 2:265-281.
15. Omura T and Sato R (1964) Carbon monoxide-binding pigment of liver microsomes: I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
16. Patton S and Benson AA (1966) Phytol metabolism in the bovine. Biochim Biophys Acta 125:22-32.
17. Powell PK, Wolf I, and Lasker JM (1996) Identification of CYP4A11 as the major lauric acid ω-hydroxylase in human liver microsomes. Arch Biochem Biophys 335:219-226.
18. Raucy JL, Lasker J, Ozaki K, and Zoleta V (2004) Regulation of CYP2E1 by ethanol and palmitic acid and CYP4A11 by clofibrate in primary cultures of human hepatocytes. Toxicol Sci 79:233-241.
19. Reddy JK, Azarnoff DL, and Hignite CE (1980) Hypolipidaemic hepatic peroxisome proliferators form a novel class of chemical carcinogens. Nature (Lond) 283:397-398.
20. Refsum S (1981) Heredopathia atactica polyneuritiformis phytanic-acid storage disease, "Refsum's disease": a biochemically well-defined disease with a specific dietary treatment. Arch Neurol 38:605-606.
21. Sanders R-J, Ofman R, Valianpour F, Kemp S, and Wanders RJA (2005) Evidence for two enzymatic pathways for ω-oxidation of docosanoic acid in rat liver microsomes. J Lipid Res 46:1001-1008.
22. Savas Ü, Griffin KJ, and Johnson EF (1999) Molecular mechanisms of cytochrome P450 induction by xenobiotics: an expanded role for nuclear hormone receptors. Mol Pharmacol 56:851-857.
23. Savas Ü, Hsu M, and Johnson EF (2003) Differential regulation of human CYP4 genes by peroxisome proliferators and dexamethasone. Arch Biochem Biophys 409:212-220.
24. Su P, Kaushal KM, and Kroetz DL (1998) Inhibition of renal arachidonic acid omega-hydroxylase activity with ABT reduces blood pressure in the SHR. Am J Physiol 275:R426-R438.
25. ten Brink HJ, Schor DS, Kok RM, Stellaard F, Kneer J, Poll-The BT, Saudubray BT, and Jakobs C (1992) In vivo study of phytanic acid alpha-oxidation in classic Refsum's disease and chondrodysplasia punctata. Pediatr Res 32:566-570.
26. Wanders RJA, Jansen GA, and Lloyd MD (2003) Phytanic acid alpha-oxidation, new insights into an old problem: a review. Biochim Biophys Acta 1631:119-135.
27. Xu F, Falck JR, Ortiz de Montellano PR, and Kroetz DL (2004) Catalytic activity and isoform-specific inhibition of rat cytochrome P450 4F enzymes. J Pharmacol Exp Ther 308:887-895.