Characterization of arachidonic acid metabolism by rat cytochrome P450 enzymes: The involvement of CYP1As

Drug Metabolism and Disposition

Volumn 42, Issue 9, 2014, Pages 1498-1507

  El Sherbeni, Ahmed A ^a   El Kadi, Ayman O S ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA-NAPHTHOFLAVONE; ARACHIDONIC ACID; BENZOFLAVONE DERIVATIVE; CYTOCHROME P450;

ANIMAL; KINETICS; LIVER MICROSOME; MALE; METABOLISM; RAT; SPRAGUE DAWLEY RAT;

ANIMALS; ARACHIDONIC ACID; BENZOFLAVONES; CYTOCHROME P-450 ENZYME SYSTEM; KINETICS; MALE; MICROSOMES, LIVER; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84906852511     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.114.057836     Document Type: Article

References (56)

1. Agbor LN, Walsh MT, Boberg JR, and Walker MK (2012) Elevated blood pressure in cytochrome P4501A1 knockout mice is associated with reduced vasodilation to omega-3 polyunsaturated fatty acids. Toxicol Appl Pharmacol 264:351-360.
2. Alkayed NJ, Goyagi T, Joh HD, Klaus J, Harder DR, Traystman RJ, and Hurn PD (2002) Neuroprotection and P450 2C11 upregulation after experimental transient ischemic attack. Stroke 33:1677-1684. (Pubitemid 34619978)
3. Alonso-Galicia M, Falck JR, Reddy KM, and Roman RJ (1999) 20-HETE agonists and antagonists in the renal circulation. Am J Physiol 277:F790-F796.
4. Barakat MM, El-Kadi AO, and du Souich P (2001) L-NAME prevents in vivo the inactivation but not the down-regulation of hepatic cytochrome P450 caused by an acute inflammatory reaction. Life Sci 69:1559-1571. (Pubitemid 32786729)
5. Bednar MM, Gross CE, Balazy MK, Belosludtsev Y, Colella DT, Falck JR, and Balazy M (2000) 16(R)-hydroxy-5,8,11,14-eicosatetraenoic acid, a new arachidonate metabolite in human polymorphonuclear leukocytes. Biochem Pharmacol 60:447-455. (Pubitemid 30336643)
6. Benassayag C, Mignot TM, Haourigui M, Civel C, Hassid J, Carbonne B, Nunez EA, and Ferre F (1997) High polyunsaturated fatty acid, thromboxane A2, and alpha-fetoprotein concentrations at the human feto-maternal interface. J Lipid Res 38:276-286. (Pubitemid 27118040)
7. Blewett AJ, Varma D, Gilles T, Libonati JR, and Jansen SA (2008) Development and validation of a high-performance liquid chromatography- electrospray mass spectrometry method for the simultaneous determination of 23 eicosanoids. J Pharm Biomed Anal 46:653-662.
8. Brash AR (2001) Arachidonic acid as a bioactive molecule. J Clin Invest 107:1339-1345.
9. Bylund J, Kunz T, Valmsen K, and Oliw EH (1998) Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes. J Pharmacol Exp Ther 284:51-60. (Pubitemid 28109528)
10. Capdevila JH (2007) Regulation of ion transport and blood pressure by cytochrome p450 monooxygenases. Curr Opin Nephrol Hypertens 16: 465-470.
11. Capdevila JH, Falck JR, and Harris RC (2000) Cytochrome P450 and arachidonic acid bio-activation. Molecular and functional properties of the arachidonate monooxygenase. J Lipid Res 41:163-181. (Pubitemid 30117856)
12. Carlson GP, Hynes DE, and Mantick NA (1998) Effects of inhibitors of CYP1A and CYP2B on styrene metabolism in mouse liver and lung microsomes. Toxicol Lett 98:131-137. (Pubitemid 28403577)
13. Carroll MA, Balazy M, Huang DD, Rybalova S, Falck JR, and McGiff JC (1997) Cytochrome P450-derived renal HETEs: storage and release. Kidney Int 51:1696-1702. (Pubitemid 27252736)
14. Choudhary D, Jansson I, Stoilov I, Sarfarazi M, and Schenkman JB (2004) Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos 32:840-847. (Pubitemid 38955614)
15. Couroucli XI, Welty SE, Geske RS, and Moorthy B (2002) Regulation of pulmonary and hepatic cytochrome P4501A expression in the rat by hyperoxia: implications for hyperoxic lung injury. Mol Pharmacol 61:507-515. (Pubitemid 34171916)
16. Edpuganti V and Mehvar R (2013) UHPLC-MS/MS analysis of arachidonic acid and 10 of its major cytochrome P450 metabolites as free acids in rat livers: Effects of hepatic ischemia. J Chromatogr B Analyt Technol Biomed Life Sci 964:153-163.
17. El-Sherbeni AA, Aboutabl ME, Zordoky BN, Anwar-Mohamed A, and El-Kadi AO (2013) Determination of the dominant arachidonic acid cytochrome p450 monooxygenases in rat heart, lung, kidney, and liver: protein expression and metabolite kinetics. AAPS J 15:112-122.
18. Elsherbiny ME, El-Kadi AO, and Brocks DR (2010) The effect of beta-naphthoflavone on the metabolism of amiodarone by hepatic and extra-hepatic microsomes. Toxicol Lett 195: 147-154.
19. Fernandez-Salguero P, Pineau T, Hilbert DM, McPhail T, Lee SS, Kimura S, Nebert DW, Rudikoff S, Ward JM, and Gonzalez FJ (1995) Immune system impairment and hepatic fibrosis in mice lacking the dioxin-binding Ah receptor. Science 268:722-726.
20. Hammarström S, Hamberg M, Samuelsson B, Duell EA, Stawiski M, and Voorhees JJ (1975) Increased concentrations of nonesterified arachidonic acid, 12L-hydroxy-5,8,10,14-eicosatetraenoic acid, prostaglandin E2, and prostaglandin F2alpha in epidermis of psoriasis. Proc Natl Acad Sci USA 72:5130-5134.
21. Holla VR, Makita K, Zaphiropoulos PG, and Capdevila JH (1999) The kidney cytochrome P-450 2C23 arachidonic acid epoxygenase is upregulated during dietary salt loading. J Clin Invest 104:751-760. (Pubitemid 29536360)
22. Houston JB and Kenworthy KE (2000) In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab Dispos 28:246-254. (Pubitemid 30137047)
23. Iliff JJ, Jia J, Nelson J, Goyagi T, Klaus J, and Alkayed NJ (2010) Epoxyeicosanoid signaling in CNS function and disease. Prostaglandins Other Lipid Mediat 91:68-84.
24. Imaoka S, Hashizume T, and Funae Y (2005) Localization of rat cytochrome P450 in various tissues and comparison of arachidonic acid metabolism by rat P450 with that by human P450 orthologs. Drug Metab Pharmacokinet 20:478-484.
25. Imig JD (2012) Epoxides and soluble epoxide hydrolase in cardiovascular physiology. Physiol Rev 92:101-130.
26. Jiang W, Welty SE, Couroucli XI, Barrios R, Kondraganti SR, Muthiah K, Yu L, Avery SE, and Moorthy B (2004) Disruption of the Ah receptor gene alters the susceptibility of mice to oxygen-mediated regulation of pulmonary and hepatic cytochromes P4501A expression and exacerbates hyperoxic lung injury. J Pharmacol Exp Ther 310:512-519. (Pubitemid 38988894)
27. Kapelyukh Y, Paine MJ, Maréchal JD, Sutcliffe MJ, Wolf CR, and Roberts GC (2008) Multiple substrate binding by cytochrome P450 3A4: estimation of the number of bound substrate molecules. Drug Metab Dispos 36:2136-2144.
28. Kayama Y, Minamino T, Toko H, Sakamoto M, Shimizu I, Takahashi H, Okada S, Tateno K, Moriya J, and Yokoyama M, et al. (2009) Cardiac 12/15 lipoxygenase-induced inflammation is involved in heart failure. J Exp Med 206:1565-1574.
29. Kiss L, Schütte H, Mayer K, Grimm H, Padberg W, Seeger W, and Grimminger F (2000) Synthesis of arachidonic acid-derived lipoxygenase and cytochrome P450 products in the intact human lung vasculature. Am J Respir Crit Care Med 161:1917-1923. (Pubitemid 30418130)
30. Kramer MA and Tracy TS (2008) Studying cytochrome P450 kinetics in drug metabolism. Expert Opin Drug Metab Toxicol 4:591-603. (Pubitemid 351890741)
31. Laethem RM, Balazy M, Falck JR, Laethem CL, and Koop DR (1993) Formation of 19(S)-, 19 (R)-, and 18(R)-hydroxyeicosatetraenoic acids by alcohol-inducible cytochrome P450 2E1. J Biol Chem 268:12912-12918. (Pubitemid 23182463)
32. Lee SS, Buters JT, Pineau T, Fernandez-Salguero P, and Gonzalez FJ (1996) Role of CYP2E1 in the hepatotoxicity of acetaminophen. J Biol Chem 271:12063-12067. (Pubitemid 26157285)
33. LiCata VJ and Allewell NM (1997) Is substrate inhibition a consequence of allostery in aspartate transcarbamylase? Biophys Chem 64:225-234.
34. Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, and Shou M (2001) Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos 29: 368-374. (Pubitemid 32275548)
35. Liu M and Alkayed NJ (2005) Hypoxic preconditioning and tolerance via hypoxia inducible factor (HIF) 1alpha-linked induction of P450 2C11 epoxygenase in astrocytes. J Cereb Blood Flow Metab 25:939-948. (Pubitemid 41061709)
36. Lowry OH, Rosebrough NJ, Farr AL, and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
37. Lund AK, Goens MB, Kanagy NL, and Walker MK (2003) Cardiac hypertrophy in aryl hydrocarbon receptor null mice is correlated with elevated angiotensin II, endothelin-1, and mean arterial blood pressure. Toxicol Appl Pharmacol 193:177-187. (Pubitemid 37476433)
38. Martignoni M, Groothuis GM, and de Kanter R (2006) Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opin Drug Metab Toxicol 2:875-894. (Pubitemid 44911538)
39. Morisseau C (2013) Role of epoxide hydrolases in lipid metabolism. Biochimie 95:91-95.
40. Nakajima T, Wang RS, Elovaara E, Park SS, Gelboin HV, and Vainio H (1992) A comparative study on the contribution of cytochrome P450 isozymes to metabolism of benzene, toluene and trichloroethylene in rat liver. Biochem Pharmacol 43:251-257.
41. Norris PC, Reichart D, Dumlao DS, Glass CK, and Dennis EA (2011) Specificity of eicosanoid production depends on the TLR-4-stimulated macrophage phenotype. J Leukoc Biol 90:563-574.
42. Peterson TC, Hodgson P, Fernandez-Salguero P, Neumeister M, and Gonzalez FJ (2000) Hepatic fibrosis and cytochrome P450: experimental models of fibrosis compared to AHR knockout mice. Hepatol Res 17:112-125. (Pubitemid 30175936)
43. Poloyac SM, Tortorici MA, Przychodzin DI, Reynolds RB, Xie W, Frye RF, and Zemaitis MA (2004) The effect of isoniazid on CYP2E1- and CYP4A-mediated hydroxylation of arachidonic acid in the rat liver and kidney. Drug Metab Dispos 32:727-733. (Pubitemid 38821874)
44. Reddy MA, Thimmalapura PR, Lanting L, Nadler JL, Fatima S, and Natarajan R (2002) The oxidized lipid and lipoxygenase product 12(S)- hydroxyeicosatetraenoic acid induces hypertrophy and fibronectin transcription in vascular smooth muscle cells via p38 MAPK and cAMP response element-binding protein activation.Mediation of angiotensin II effects. J Biol Chem 277:9920-9928. (Pubitemid 34968098)
45. Reed MC, Lieb A, and Nijhout HF (2010) The biological significance of substrate inhibition: a mechanism with diverse functions. BioEssays 32:422-429.
46. Reid JM, Kuffel MJ, Miller JK, Rios R, and Ames MM (1999) Metabolic activation of dacarbazine by human cytochromes P450: the role of CYP1A1, CYP1A2, and CYP2E1. Clin Cancer Res 5: 2192-2197. (Pubitemid 29399277)
47. Roman RJ (2002) P-450 metabolites of arachidonic acid in the control of cardiovascular function. Physiol Rev 82:131-185.
48. Roman RJ, Maier KG, Sun CW, Harder DR, and Alonso-Galicia M (2000) Renal and cardiovascular actions of 20-hydroxyeicosatetraenoic acid and epoxyeicosatrienoic acids. Clin Exp Pharmacol Physiol 27:855-865.
49. Schwarz D, Kisselev P, Ericksen SS, Szklarz GD, Chernogolov A, Honeck H, Schunck WH, and Roots I (2004) Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: highly stereoselective formation of 17(R),18(S)- epoxyeicosatetraenoic acid. Biochem Pharmacol 67:1445-1457. (Pubitemid 38388207)
50. Stec DE, Gannon KP, Beaird JS, and Drummond HA (2007) 20-Hydroxyeicosatetraenoic acid (20-HETE) stimulates migration of vascular smooth muscle cells. Cell Physiol Biochem 19: 121-128.
51. van Herwaarden AE, Wagenaar E, van der Kruijssen CM, van Waterschoot RA, Smit JW, Song JY, van der Valk MA, van Tellingen O, van der Hoorn JW, and Rosing H, et al. (2007) Knockout of cytochrome P450 3A yields new mouse models for understanding xenobiotic metabolism. J Clin Invest 117: 3583-3592. (Pubitemid 350097013)
52. 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. (Pubitemid 38263962)
53. Yeung CK, Shen DD, Thummel KE, and Himmelfarb J (2014) Effects of chronic kidney disease and uremia on hepatic drug metabolism and transport. Kidney Int 85:522-528.
54. Zhang F, Deng H, Kemp R, Singh H, Gopal VR, Falck JR, Laniado-Schwartzman M, and Nasjletti A (2005) Decreased levels of cytochrome P450 2E1-derived eicosanoids sensitize renal arteries to constrictor agonists in spontaneously hypertensive rats. Hypertension 45:103-108. (Pubitemid 40066422)
55. Zordoky BN, Aboutabl ME, and El-Kadi AO (2008) Modulation of cytochrome P450 gene expression and arachidonic acid metabolism during isoproterenol- induced cardiac hypertrophy in rats. Drug Metab Dispos 36:2277-2286.
56. Zou AP, Fleming JT, Falck JR, Jacobs ER, Gebremedhin D, Harder DR, and Roman RJ (1996) 20-HETE is an endogenous inhibitor of the large-conductance Ca(2+)-activated K+ channel in renal arterioles. Am J Physiol 270:R228-R237.