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Cytochrome P450 4F2

Definition:

A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, eicosanoids and vitamins. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase). Catalyzes predominantly the oxidation of the terminal carbon (omega-oxidation) of long- and very long-chain fatty acids. Displays high omega-hydroxylase activity toward polyunsaturated fatty acids (PUFAs). Participates in the conversion of arachidonic acid to omega-hydroxyeicosatetraenoic acid (20-HETE), a signaling molecule acting both as vasoconstrictive and natriuretic with overall effect on arterial blood pressure. Plays a role in the oxidative inactivation of eicosanoids, including both pro-inflammatory and anti-inflammatory mediators such as leukotriene B4 (LTB4), lipoxin A4 (LXA4), and several HETEs. Catalyzes omega-hydroxylation of 3-hydroxy fatty acids. Converts monoepoxides of linoleic acid leukotoxin and isoleukotoxin to omega-hydroxylated metabolites. Contributes to the degradation of very long-chain fatty acids (VLCFAs) by catalyzing successive omega-oxidations and chain shortening. Plays an important role in vitamin metabolism by chain shortening. Catalyzes omega-hydroxylation of the phytyl chain of tocopherols (forms of vitamin E), with preference for gamma-tocopherols over alpha-tocopherols, thus promoting retention of alpha-tocopherols in tissues. Omega-hydroxylates and inactivates phylloquinone (vitamin K1), and menaquinone-4 (MK-4, a form of vitamin K2), both acting as cofactors in blood coagulation.

References:

[1]. David E Stec, et al. Functional polymorphism in human CYP4F2 decreases 20-HETE production. Physiol Genomics. 2007 Jun 19;30(1):74-81. [Content Brief]

[2]. Y Kikuta, et al. Characterization of human liver leukotriene B(4) omega-hydroxylase P450 (CYP4F2). J Biochem. 2000 Jun;127(6):1047-52. [Content Brief]

[3]. Valérie Le Quéré, et al. Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides. J Lipid Res. 2004 Aug;45(8):1446-58. [Content Brief]

[4]. Y Kikuta, et al. Cloning and expression of a novel form of leukotriene B4 omega-hydroxylase from human liver. FEBS Lett. 1994 Jul 4;348(1):70-4. [Content Brief]

[5]. R Jin, et al. Role of human CYP4F2 in hepatic catabolism of the proinflammatory agent leukotriene B4. Arch Biochem Biophys. 1998 Nov 1;359(1):89-98. [Content Brief]

[6]. Madhurima Dhar, et al. Omega oxidation of 3-hydroxy fatty acids by the human CYP4F gene subfamily enzyme CYP4F11. J Lipid Res. 2008 Mar;49(3):612-24. [Content Brief]

[7]. Robert-Jan Sanders, et al. Characterization of the human omega-oxidation pathway for omega-hydroxy-very-long-chain fatty acids. FASEB J. 2008 Jun;22(6):2064-71. [Content Brief]

[8]. Matthew G McDonald, et al. CYP4F2 is a vitamin K1 oxidase: An explanation for altered warfarin dose in carriers of the V433M variant. Mol Pharmacol. 2009 Jun;75(6):1337-46. [Content Brief]

[9]. Katheryne Z Edson, et al. Cytochrome P450-dependent catabolism of vitamin K: ω-hydroxylation catalyzed by human CYP4F2 and CYP4F11. Biochemistry. 2013 Nov 19;52(46):8276-85. [Content Brief]

[10]. Cristiano Fava, et al. The V433M variant of the CYP4F2 is associated with ischemic stroke in male Swedes beyond its effect on blood pressure. Hypertension. 2008 Aug;52(2):373-80. [Content Brief]

[11]. Timothy J Sontag, et al. Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem. 2002 Jul 12;277(28):25290-6. [Content Brief]

[12]. Maude Fer, et al. Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism. J Lipid Res. 2008 Nov;49(11):2379-89. [Content Brief]

[13]. J M Lasker, et al. Formation of 20-hydroxyeicosatetraenoic acid, a vasoactive and natriuretic eicosanoid, in human kidney. Role of Cyp4F2 and Cyp4A11. J Biol Chem. 2000 Feb 11;275(6):4118-26. [Content Brief]

[14]. Robert-Jan Sanders, et al. Omega-oxidation of very long-chain fatty acids in human liver microsomes. Implications for X-linked adrenoleukodystrophy. J Biol Chem. 2006 May 12;281(19):13180-13187. [Content Brief]

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