Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1814, Issue 1, 2011, Pages 210-222

  Konkel, Anne ^a   Schunck, Wolf Hagen ^a  

^a MAX DELBRÜCK CENTER FOR MOLECULAR MEDICINE   (Germany)

Author keywords

Arachidonic acid; Cardiovascular disease; Cytochrome P450; Eicosanoid; Omega 3 polyunsaturated fatty acid

Indexed keywords

20 HYDROXYICOSATETRAENOIC ACID; ADRENIC ACID; ARACHIDONIC ACID; CYTOCHROME P450; CYTOCHROME P450 1A; CYTOCHROME P450 2C; CYTOCHROME P450 2E; CYTOCHROME P450 2J; CYTOCHROME P450 4A; DOCOSAHEXAENOIC ACID; EPOXYICOSATRIENOIC ACID; ICOSAPENTAENOIC ACID; LINOLEIC ACID; OMEGA 3 FATTY ACID; OMEGA 6 FATTY ACID; POLYUNSATURATED FATTY ACID; UNCLASSIFIED DRUG;

BIOAVAILABILITY; CARDIOVASCULAR DISEASE; ENZYME STRUCTURE; EPOXIDATION; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY;

ARACHIDONIC ACID; CYTOCHROME P-450 ENZYME SYSTEM; DOCOSAHEXAENOIC ACIDS; EICOSAPENTAENOIC ACID; FATTY ACIDS, UNSATURATED; HUMANS; LINOLEIC ACID; SIGNAL TRANSDUCTION; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 78649451203     PISSN: 15709639     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbapap.2010.09.009     Document Type: Review

References (213)

1. W.L. Hall Dietary saturated and unsaturated fats as determinants of blood pressure and vascular function Nutr. Res. Rev. 22 2009 18 38
2. F.M. Sacks, and H. Campos Polyunsaturated fatty acids, inflammation, and cardiovascular disease: time to widen our view of the mechanisms J. Clin. Endocrinol. Metab. 91 2006 398 400
3. R. Uauy Dietary fat quality for optimal health and well-being: overview of recommendations Ann. Nutr. Metab. 54 Suppl 1 2009 2 7
4. P.M. Kris-Etherton, W.S. Harris, and L.J. Appel Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease Circulation 106 2002 2747 2757
5. J.H. Lee, J.H. O'Keefe, C.J. Lavie, and W.S. Harris Omega-3 fatty acids: cardiovascular benefits, sources and sustainability Nat. Rev. Cardiol. 6 2009 753 758
6. A.A. Spector Essentiality of fatty acids Lipids 34 Suppl 1999 S1 S3
7. G.L. Russo Dietary n-6 and n-3 polyunsaturated fatty acids: from biochemistry to clinical implications in cardiovascular prevention Biochem. Pharmacol. 77 2009 937 946
8. W.L. Smith, D.L. DeWitt, and R.M. Garavito Cyclooxygenases: structural, cellular, and molecular biology Annu. Rev. Biochem. 69 2000 145 182
9. D.L. Simmons, R.M. Botting, and T. Hla Cyclooxygenase isozymes: the biology of prostaglandin synthesis and inhibition Pharmacol. Rev. 56 2004 387 437
10. C.D. Funk Prostaglandins and leukotrienes: advances in eicosanoid biology Science 294 2001 1871 1875
11. A.R. Brash Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate J. Biol. Chem. 274 1999 23679 23682
12. H. Kuhn, J. Saam, S. Eibach, H.G. Holzhutter, I. Ivanov, and M. Walther Structural biology of mammalian lipoxygenases: enzymatic consequences of targeted alterations of the protein structure Biochem. Biophys. Res. Commun. 338 2005 93 101
13. J.H. Capdevila, and J.R. Falck Biochemical and molecular properties of the cytochrome P450 arachidonic acid monooxygenases Prostaglandins Other Lipid Mediat. 68-69 2002 325 344
14. R.J. Roman P-450 metabolites of arachidonic acid in the control of cardiovascular function Physiol. Rev. 82 2002 131 185
15. J.C. McGiff, and J. Quilley 20-HETE and the kidney: resolution of old problems and new beginnings Am. J. Physiol. 277 1999 R607 R623
16. A.A. Spector, X. Fang, G.D. Snyder, and N.L. Weintraub Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function Prog. Lipid Res. 43 2004 55 90
17. D.C. Zeldin Epoxygenase pathways of arachidonic acid metabolism J. Biol. Chem. 276 2001 36059 36062
18. I. Fleming Vascular cytochrome p450 enzymes: physiology and pathophysiology Trends Cardiovasc. Med. 18 2008 20 25
19. M.W. Buczynski, D.S. Dumlao, and E.A. Dennis Thematic Review Series: Proteomics. An integrated omics analysis of eicosanoid biology J. Lipid Res. 50 2009 1015 1038
20. L.M. Arterburn, E.B. Hall, and H. Oken Distribution, interconversion, and dose response of n-3 fatty acids in humans Am. J. Clin. Nutr. 83 2006 1467S 1476S
21. L. Schaeffer, H. Gohlke, M. Muller, I.M. Heid, L.J. Palmer, I. Kompauer, H. Demmelmair, T. Illig, B. Koletzko, and J. Heinrich Common genetic variants of the FADS1 FADS2 gene cluster and their reconstructed haplotypes are associated with the fatty acid composition in phospholipids Hum. Mol. Genet. 15 2006 1745 1756
22. B. Koletzko, H. Demmelmair, L. Schaeffer, T. Illig, and J. Heinrich Genetically determined variation in polyunsaturated fatty acid metabolism may result in different dietary requirements Nestle Nutr. Workshop Ser. Pediatr. Program. 62 2008 35 44 (discussion 44-39)
23. T. Tanaka, J. Shen, G.R. Abecasis, A. Kisialiou, J.M. Ordovas, J.M. Guralnik, A. Singleton, S. Bandinelli, A. Cherubini, D. Arnett, M.Y. Tsai, and L. Ferrucci Genome-wide association study of plasma polyunsaturated fatty acids in the InCHIANTI Study PLoS Genet. 5 2009 e1000338
24. G. Burdge Alpha-linolenic acid metabolism in men and women: nutritional and biological implications Curr. Opin. Clin. Nutr. Metab. Care 7 2004 137 144
25. C.E. Childs, M. Romeu-Nadal, G.C. Burdge, and P.C. Calder Gender differences in the n-3 fatty acid content of tissues Proc. Nutr. Soc. 67 2008 19 27
26. G.C. Burdge, and S.A. Wootton Conversion of alpha-linolenic acid to eicosapentaenoic, docosapentaenoic and docosahexaenoic acids in young women Br. J. Nutr. 88 2002 411 420
27. D. Mozaffarian Fish and n-3 fatty acids for the prevention of fatal coronary heart disease and sudden cardiac death Am. J. Clin. Nutr. 87 2008 1991S 1996S
28. A.P. Simopoulos The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases Exp. Biol. Med. (Maywood) 233 2008 674 688
29. C.J. Lavie, R.V. Milani, M.R. Mehra, and H.O. Ventura Omega-3 polyunsaturated fatty acids and cardiovascular diseases J. Am. Coll. Cardiol. 54 2009 585 594
30. R. Fischer, R. Dechend, F. Qadri, M. Markovic, S. Feldt, F. Herse, J.K. Park, A. Gapelyuk, I. Schwarz, U.B. Zacharzowsky, R. Plehm, E. Safak, A. Heuser, A. Schirdewan, F.C. Luft, W.H. Schunck, and D.N. Muller Dietary n-3 polyunsaturated fatty acids and direct renin inhibition improve electrical remodeling in a model of high human renin hypertension Hypertension 51 2008 540 546
31. A. Leaf, J.X. Kang, Y.F. Xiao, and G.E. Billman Clinical prevention of sudden cardiac death by n-3 polyunsaturated fatty acids and mechanism of prevention of arrhythmias by n-3 fish oils Circulation 107 2003 2646 2652
32. R. Marchioli, F. Barzi, E. Bomba, C. Chieffo, D. Di Gregorio, R. Di Mascio, M.G. Franzosi, E. Geraci, G. Levantesi, A.P. Maggioni, L. Mantini, R.M. Marfisi, G. Mastrogiuseppe, N. Mininni, G.L. Nicolosi, M. Santini, C. Schweiger, L. Tavazzi, G. Tognoni, C. Tucci, and F. Valagussa Early protection against sudden death by n-3 polyunsaturated fatty acids after myocardial infarction: time-course analysis of the results of the Gruppo Italiano per lo Studio della Sopravvivenza nell'Infarto Miocardico (GISSI)-Prevenzione Circulation 105 2002 1897 1903
33. N.R. Matthan, H. Jordan, M. Chung, A.H. Lichtenstein, D.A. Lathrop, and J. Lau A systematic review and meta-analysis of the impact of omega-3 fatty acids on selected arrhythmia outcomes in animal models Metabolism 54 2005 1557 1565
34. R.S. Chapkin, D.N. McMurray, L.A. Davidson, B.S. Patil, Y.Y. Fan, and J.R. Lupton Bioactive dietary long-chain fatty acids: emerging mechanisms of action Br. J. Nutr. 100 2008 1152 1157
35. D.B. Jump The biochemistry of n-3 polyunsaturated fatty acids J. Biol. Chem. 277 2002 8755 8758
36. R.J. Deckelbaum, T.S. Worgall, and T. Seo n-3 fatty acids and gene expression Am. J. Clin. Nutr. 83 2006 1520S 1525S
37. Y.F. Xiao, D.C. Sigg, and A. Leaf The antiarrhythmic effect of n-3 polyunsaturated fatty acids: modulation of cardiac ion channels as a potential mechanism J. Membr. Biol. 206 2005 141 154
38. P.C. Calder n-3 polyunsaturated fatty acids, inflammation, and inflammatory diseases Am. J. Clin. Nutr. 83 2006 1505S 1519S
39. C.N. Serhan, N. Chiang, and T.E. Van Dyke Resolving inflammation: dual anti-inflammatory and pro-resolution lipid mediators Nat. Rev. Immunol. 8 2008 349 361
40. G. Schmitz, and J. Ecker The opposing effects of n-3 and n-6 fatty acids Prog. Lipid Res. 47 2008 147 155
41. M. Wada, C.J. DeLong, Y.H. Hong, C.J. Rieke, I. Song, R.S. Sidhu, C. Yuan, M. Warnock, A.H. Schmaier, C. Yokoyama, E.M. Smyth, S.J. Wilson, G.A. FitzGerald, R.M. Garavito, and X. Sui Test Enzymes and receptors of prostaglandin pathways with arachidonic acid-derived versus eicosapentaenoic acid-derived substrates and products J. Biol. Chem. 282 2007 22254 22266
42. E.H. Oliw, J. Bylund, and C. Herman Bisallylic hydroxylation and epoxidation of polyunsaturated fatty acids by cytochrome P450 Lipids 31 1996 1003 1021 (Pubitemid 26338032)
43. J.H. Capdevila, J.R. Falck, and R.C. Harris Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase J. Lipid Res. 41 2000 163 181
44. D.L. Kroetz, and F. Xu Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation Annu. Rev. Pharmacol. Toxicol. 45 2005 413 438
45. F. Xu, J.R. Falck, P.R. Ortiz de Montellano, and D.L. Kroetz Catalytic activity and isoform-specific inhibition of rat cytochrome p450 4F enzymes J. Pharmacol. Exp. Ther. 308 2004 887 895
46. J.V. Gainer, A. Bellamine, E.P. Dawson, K.E. Womble, S.W. Grant, Y. Wang, L.A. Cupples, C.Y. Guo, S. Demissie, C.J. O'Donnell, N.J. Brown, M.R. Waterman, and J.H. Capdevila Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension Circulation 111 2005 63 69
47. D.N. Muller, C. Schmidt, E. Barbosa-Sicard, M. Wellner, V. Gross, H. Hercule, M. Markovic, H. Honeck, F.C. Luft, and W.H. Schunck Mouse Cyp4a isoforms: enzymatic properties, gender- and strain-specific expression, and role in renal 20-hydroxyeicosatetraenoic acid formation Biochem. J. 403 2007 109 118
48. X. Nguyen, M.H. Wang, K.M. Reddy, J.R. Falck, and M.L. Schwartzman Kinetic profile of the rat CYP4A isoforms: arachidonic acid metabolism and isoform-specific inhibitors Am. J. Physiol. 276 1999 R1691 R1700
49. M. Fer, L. Corcos, Y. Dreano, E. Plee-Gautier, J.P. Salaun, F. Berthou, and Y. Amet Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism J. Lipid Res. 49 2008 2379 2389
50. 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 1990 10244 10249
51. D. Schwarz, P. Kisselev, S.S. Ericksen, G.D. Szklarz, A. Chernogolov, H. Honeck, W.H. Schunck, and I. Roots Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: highly stereoselective formation of 17(R),18(S)-epoxyeicosatetraenoic acid Biochem. Pharmacol. 67 2004 1445 1457
52. A.B. Rifkind, C. Lee, T.K. 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 1995 380 389
53. R.M. Laethem, M. Balazy, J.R. Falck, C.L. Laethem, and D.R. Koop Formation of 19(S)-, 19(R)-, and 18(R)-hydroxyeicosatetraenoic acids by alcohol-inducible cytochrome P450 2E1 J. Biol. Chem. 268 1993 12912 12918
54. W. Qu, J.A. Bradbury, C.C. Tsao, R. Maronpot, G.J. Harry, C.E. Parker, L.S. Davis, M.D. Breyer, M.P. Waalkes, J.R. Falck, J. Chen, R.L. Rosenberg, and D.C. Zeldin Cytochrome P450 CYP2J9, a new mouse arachidonic acid omega-1 hydroxylase predominantly expressed in brain J. Biol. Chem. 276 2001 25467 25479
55. S. Wu, C.R. Moomaw, K.B. Tomer, J.R. Falck, and D.C. Zeldin Molecular cloning and expression of CYP2J2, a human cytochrome P450 arachidonic acid epoxygenase highly expressed in heart J. Biol. Chem. 271 1996 3460 3468
56. S. Wu, W. Chen, E. Murphy, S. Gabel, K.B. Tomer, J. Foley, C. Steenbergen, J.R. Falck, C.R. Moomaw, and D.C. Zeldin Molecular cloning, expression, and functional significance of a cytochrome P450 highly expressed in rat heart myocytes J. Biol. Chem. 272 1997 12551 12559
57. C.C. Tsao, J. Foley, S.J. Coulter, R. Maronpot, D.C. Zeldin, and J.A. Goldstein CYP2C40, a unique arachidonic acid 16-hydroxylase, is the major CYP2C in murine intestinal tract Mol. Pharmacol. 58 2000 279 287
58. 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 P-450 arachidonic acid epoxygenase J. Biol. Chem. 268 1993 13565 13570
59. T.C. DeLozier, C.C. Tsao, S.J. Coulter, J. Foley, J.A. Bradbury, D.C. Zeldin, and J.A. Goldstein CYP2C44, a new murine CYP2C that metabolizes arachidonic acid to unique stereospecific products J. Pharmacol. Exp. Ther. 310 2004 845 854
60. D.C. Zeldin, R.N. DuBois, J.R. Falck, and J.H. Capdevila Molecular cloning, expression and characterization of an endogenous human cytochrome P450 arachidonic acid epoxygenase isoform Arch. Biochem. Biophys. 322 1995 76 86
61. 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 1994 1427 1433
62. D.S. Keeney, C. Skinner, J.B. Travers, J.H. Capdevila, L.B. Nanney, L.E. King Jr., and M.R. Waterman Differentiating keratinocytes express a novel cytochrome P450 enzyme, CYP2B19, having arachidonate monooxygenase activity J. Biol. Chem. 273 1998 32071 32079
63. L. Hornsten, J. Bylund, and E.H. Oliw Dexamethasone induces bisallylic hydroxylation of polyunsaturated fatty acids by rat liver microsomes Arch. Biochem. Biophys. 332 1996 261 268
64. J. Bylund, T. Kunz, K. Valmsen, and E.H. Oliw 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 1998 51 60
65. J. Bylund, J. Ericsson, and E.H. Oliw Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS Anal. Biochem. 265 1998 55 68
66. A.R. Brash, W.E. Boeglin, J.H. Capdevila, S. Yeola, and I.A. Blair 7-HETE, 10-HETE, and 13-HETE are major products of NADPH-dependent arachidonic acid metabolism in rat liver microsomes: analysis of their stereochemistry, and the stereochemistry of their acid-catalyzed rearrangement Arch. Biochem. Biophys. 321 1995 485 492
67. I. Kudo, and M. Murakami Phospholipase A2 enzymes Prostaglandins Other Lipid Mediat. 68-69 2002 3 58
68. G. Perez-Chacon, A.M. Astudillo, D. Balgoma, M.A. Balboa, and J. Balsinde Control of free arachidonic acid levels by phospholipases A2 and lysophospholipid acyltransferases Biochim. Biophys. Acta 1791 2009 1103 1113
69. C.M. Jenkins, A. Cedars, and R.W. Gross Eicosanoid signalling pathways in the heart Cardiovasc. Res. 82 2009 240 249
70. A. Karara, E. Dishman, J.R. Falck, and J.H. Capdevila Endogenous epoxyeicosatrienoyl-phospholipids. A novel class of cellular glycerolipids containing epoxidized arachidonate moieties J. Biol. Chem. 266 1991 7561 7569
71. M.A. Carroll, M. Balazy, D.D. Huang, S. Rybalova, J.R. Falck, and J.C. McGiff Cytochrome P450-derived renal HETEs: storage and release Kidney Int. 51 1997 1696 1702
72. T.L. Kaduce, X. Fang, S.D. Harmon, C.L. Oltman, K.C. Dellsperger, L.M. Teesch, V.R. Gopal, J.R. Falck, W.B. Campbell, N.L. Weintraub, and A.A. Spector 20-Hydroxyeicosatetraenoic acid (20-HETE) metabolism in coronary endothelial cells J. Biol. Chem. 279 2004 2648 2656
73. J.W. Phillis, and M.H. O'Regan A potentially critical role of phospholipases in central nervous system ischemic, traumatic, and neurodegenerative disorders Brain Res. Brain Res. Rev. 44 2004 13 47
74. H. Nakamura, R.A. Nemenoff, J.H. Gronich, and J.V. Bonventre Subcellular characteristics of phospholipase A2 activity in the rat kidney. Enhanced cytosolic, mitochondrial, and microsomal phospholipase A2 enzymatic activity after renal ischemia and reperfusion J. Clin. Invest. 87 1991 1810 1818
75. C.M. Mansbach, and S.A. Siddiqi The biogenesis of chylomicrons Annu. Rev. Physiol. 72 2010 315 333
76. D.C. Zeldin, J. Foley, S.M. Goldsworthy, M.E. Cook, J.E. Boyle, J. Ma, C.R. Moomaw, K.B. Tomer, C. Steenbergen, and S. Wu CYP2J subfamily cytochrome P450s in the gastrointestinal tract: expression, localization, and potential functional significance Mol. Pharmacol. 51 1997 931 943
77. E.R. Jacobs, and D.C. Zeldin The lung HETEs (and EETs) up Am. J. Physiol. Heart Circ. Physiol. 280 2001 H1 H10
78. B. Keseru, E. Barbosa-Sicard, R. Popp, B. Fisslthaler, A. Dietrich, T. Gudermann, B.D. Hammock, J.R. Falck, N. Weissmann, R. Busse, and I. Fleming Epoxyeicosatrienoic acids and the soluble epoxide hydrolase are determinants of pulmonary artery pressure and the acute hypoxic pulmonary vasoconstrictor response FASEB J. 22 2008 4306 4315
79. A.E. Loot, I. Fleming, Cytochrome P450-derived epoxyeicosatrienoic acids and pulmonary hypertension: central role of transient receptor potential (TRP) C6 channels. J. Cardiovasc. Pharmacol 2010, Jun 24. Epub ahead of print.
80. C. Zheng, L. Wang, R. Li, B. Ma, L. Tu, X. Xu, R.T. Dackor, D.C. Zeldin, D.W. Wang, Gene delivery of a cytochrome P450 epoxygenase ameliorates monocrotaline-induced pulmonary artery hypertension in rats. Am. J. Respir. Cell Mol. Biol. 2010, Jan 29, Epub ahead of print.
81. D. Sacerdoti, A. Gatta, and J.C. McGiff Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology Prostaglandins Other Lipid Mediat. 72 2003 51 71
82. J.R. Falck, S. Manna, J. Moltz, N. Chacos, and J. Capdevila Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets Biochem. Biophys. Res. Commun. 114 1983 743 749
83. D.C. Zeldin, J. Foley, J.E. Boyle, C.R. Moomaw, K.B. Tomer, C. Parker, C. Steenbergen, and S. Wu Predominant expression of an arachidonate epoxygenase in islets of Langerhans cells in human and rat pancreas Endocrinology 138 1997 1338 1346
84. S. Mustafa, V. Sharma, and J.H. McNeill Insulin resistance and endothelial dysfunction: are epoxyeicosatrienoic acids the link? Exp. Clin. Cardiol. 14 2009 e41 e50
85. M. Terashvili, L.F. Tseng, H.E. Wu, J. Narayanan, L.M. Hart, J.R. Falck, P.F. Pratt, and D.R. Harder Antinociception produced by 14,15- epoxyeicosatrienoic acid is mediated by the activation of beta-endorphin and met-enkephalin in the rat ventrolateral periaqueductal gray J. Pharmacol. Exp. Ther. 326 2008 614 622
86. J.J. Iliff, J. Jia, J. Nelson, T. Goyagi, J. Klaus, and N.J. Alkayed Epoxyeicosanoid signaling in CNS function and disease Prostaglandins Other Lipid Mediat. 91 2010 68 84
87. J.D. Imig Eicosanoid regulation of the renal vasculature Am. J. Physiol. Renal Physiol. 279 2000 F965 F981
88. V. Randriamboavonjy, R. Busse, and I. Fleming 20-HETE-induced contraction of small coronary arteries depends on the activation of Rho-kinase Hypertension 41 2003 801 806
89. D. Gebremedhin, A.R. Lange, J. Narayanan, M.R. Aebly, E.R. Jacobs, and D.R. Harder Cat cerebral arterial smooth muscle cells express cytochrome P450 4A2 enzyme and produce the vasoconstrictor 20-HETE which enhances L-type Ca2+ current J. Physiol. 507 Pt 3 1998 771 781
90. J.S. Wang, H. Singh, F. Zhang, T. Ishizuka, H. Deng, R. Kemp, M.S. Wolin, T.H. Hintze, N.G. Abraham, A. Nasjletti, and M. Laniado-Schwartzman Endothelial dysfunction and hypertension in rats transduced with CYP4A2 adenovirus Circ. Res. 98 2006 962 969
91. J. Cheng, J.S. Ou, H. Singh, J.R. Falck, D. Narsimhaswamy, K.A. Pritchard Jr., and M.L. Schwartzman 20-Hydroxyeicosatetraenoic acid causes endothelial dysfunction via eNOS uncoupling Am. J. Physiol. Heart Circ. Physiol. 294 2008 H1018 H1026
92. T. Ishizuka, J. Cheng, H. Singh, M.D. Vitto, V.L. Manthati, J.R. Falck, and M. Laniado-Schwartzman 20-Hydroxyeicosatetraenoic acid stimulates nuclear factor-kappaB activation and the production of inflammatory cytokines in human endothelial cells J. Pharmacol. Exp. Ther. 324 2008 103 110
93. H. Singh, J. Cheng, H. Deng, R. Kemp, T. Ishizuka, A. Nasjletti, and M.L. Schwartzman Vascular cytochrome P450 4A expression and 20- hydroxyeicosatetraenoic acid synthesis contribute to endothelial dysfunction in androgen-induced hypertension Hypertension 50 2007 123 129
94. A. Blanton, R. Nsaif, H. Hercule, and A. Oyekan Nitric oxide/cytochrome P450 interactions in cyclosporin A-induced effects in the rat J. Hypertens. 24 2006 1865 1872
95. H. Singh, and M.L. Schwartzman Renal vascular cytochrome P450-derived eicosanoids in androgen-induced hypertension Pharmacol. Rep. 60 2008 29 37
96. K. Nithipatikom, E.R. Gross, M.P. Endsley, J.M. Moore, M.A. Isbell, J.R. Falck, W.B. Campbell, and G.J. Gross Inhibition of cytochrome P450omega-hydroxylase: a novel endogenous cardioprotective pathway Circ. Res. 95 2004 e65 e71
97. N. Miyata, T. Seki, Y. Tanaka, T. Omura, K. Taniguchi, M. Doi, K. Bandou, S. Kametani, M. Sato, S. Okuyama, L. Cambj-Sapunar, D.R. Harder, and R.J. Roman Beneficial effects of a new 20-hydroxyeicosatetraenoic acid synthesis inhibitor, TS-011 [N-(3-chloro-4-morpholin-4-yl) phenyl-N′-hydroxyimido formamide], on hemorrhagic and ischemic stroke J. Pharmacol. Exp. Ther. 314 2005 77 85
98. R.J. Roman, M. Alonso-Galicia, and T.W. Wilson Renal P450 metabolites of arachidonic acid and the development of hypertension in Dahl salt-sensitive rats Am. J. Hypertens. 10 1997 63S 67S
99. H. Honeck, V. Gross, B. Erdmann, E. Kargel, R. Neunaber, A.F. Milia, W. Schneider, F.C. Luft, and W.H. Schunck Cytochrome P450-dependent renal arachidonic acid metabolism in desoxycorticosterone acetate-salt hypertensive mice Hypertension 36 2000 610 616
100. K.M. Hoagland, A.K. Flasch, and R.J. Roman Inhibitors of 20-HETE formation promote salt-sensitive hypertension in rats Hypertension 42 2003 669 673
101. N.C. Ward, J. Rivera, J. Hodgson, I.B. Puddey, L.J. Beilin, J.R. Falck, and K.D. Croft Urinary 20-hydroxyeicosatetraenoic acid is associated with endothelial dysfunction in humans Circulation 110 2004 438 443
102. M. Hermann, J.P. Hellermann, K. Quitzau, M.M. Hoffmann, T. Gasser, T. Meinertz, T. Munzel, I. Fleming, and T.F. Luscher CYP4A11 polymorphism correlates with coronary endothelial dysfunction in patients with coronary artery disease-the ENCORE Trials Atherosclerosis 207 2009 476 479
103. C. Fava, M. Montagnana, P. Almgren, L. Rosberg, G. Lippi, B. Hedblad, G. Engstrom, G. Berglund, P. Minuz, and O. Melander The V433M variant of the CYP4F2 is associated with ischemic stroke in male Swedes beyond its effect on blood pressure Hypertension 52 2008 373 380
104. B.N. Zordoky, and A.O. El-Kadi Effect of cytochrome P450 polymorphism on arachidonic acid metabolism and their impact on cardiovascular diseases Pharmacol. Ther. 125 2010 446 463
105. M.A. Carroll, M. Balazy, P. Margiotta, D.D. Huang, J.R. Falck, and J.C. McGiff Cytochrome P-450-dependent HETEs: profile of biological activity and stimulation by vasoactive peptides Am. J. Physiol. 271 1996 R863 R869
106. M. Alonso-Galicia, J.R. Falck, K.M. Reddy, and R.J. Roman 20-HETE agonists and antagonists in the renal circulation Am. J. Physiol. 277 1999 F790 F796
107. F. Zhang, H. Deng, R. Kemp, H. Singh, V.R. Gopal, J.R. Falck, M. Laniado-Schwartzman, and A. Nasjletti Decreased levels of cytochrome P450 2E1-derived eicosanoids sensitize renal arteries to constrictor agonists in spontaneously hypertensive rats Hypertension 45 2005 103 108
108. W.B. Campbell, D. Gebremedhin, P.F. Pratt, and D.R. Harder Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors Circ. Res. 78 1996 415 423
109. W.B. Campbell, and J.R. Falck Arachidonic acid metabolites as endothelium-derived hyperpolarizing factors Hypertension 49 2007 590 596
110. B. Fisslthaler, R. Popp, L. Kiss, M. Potente, D.R. Harder, I. Fleming, and R. Busse Cytochrome P450 2C is an EDHF synthase in coronary arteries Nature 401 1999 493 497 (Pubitemid 29470209)
111. H.C. Hercule, W.H. Schunck, V. Gross, J. Seringer, F.P. Leung, S.M. Weldon, A. da Costa Goncalves, Y. Huang, F.C. Luft, and M. Gollasch Interaction between P450 eicosanoids and nitric oxide in the control of arterial tone in mice Arterioscler. Thromb. Vasc. Biol. 29 2009 54 60
112. H. Wang, L. Lin, J. Jiang, Y. Wang, Z.Y. Lu, J.A. Bradbury, F.B. Lih, D.W. Wang, and D.C. Zeldin Up-regulation of endothelial nitric-oxide synthase by endothelium-derived hyperpolarizing factor involves mitogen-activated protein kinase and protein kinase C signaling pathways J. Pharmacol. Exp. Ther. 307 2003 753 764
113. A.E. Loot, R. Popp, B. Fisslthaler, J. Vriens, B. Nilius, and I. Fleming Role of cytochrome P450-dependent transient receptor potential V4 activation in flow-induced vasodilatation Cardiovasc. Res. 80 2008 445 452
114. Y. Wei, P. Sun, Z. Wang, B. Yang, M.A. Carroll, and W.H. Wang Adenosine inhibits ENaC via cytochrome P-450 epoxygenase-dependent metabolites of arachidonic acid Am. J. Physiol. Renal Physiol. 290 2006 F1163 F1168
115. P. Sun, D.H. Lin, T. Wang, E. Babilonia, Z. Wang, Y. Jin, R. Kemp, A. Nasjletti, and W.H. Wang Low Na intake suppresses expression of CYP2C23 and arachidonic acid-induced inhibition of ENaC Am. J. Physiol. Renal Physiol. 291 2006 F1192 F1200
116. Y.F. Xiao, L. Huang, and J.P. Morgan Cytochrome P450: a novel system modulating Ca2+ channels and contraction in mammalian heart cells J. Physiol. 508 Pt 3 1998 777 792
117. T. Lu, T. Hoshi, N.L. Weintraub, A.A. Spector, and H.C. Lee Activation of ATP-sensitive K(+) channels by epoxyeicosatrienoic acids in rat cardiac ventricular myocytes J. Physiol. 537 2001 811 827
118. H.C. Lee, T. Lu, N.L. Weintraub, M. VanRollins, A.A. Spector, and E.F. Shibata Effects of epoxyeicosatrienoic acids on the cardiac sodium channels in isolated rat ventricular myocytes J. Physiol. 519 Pt 1 1999 153 168
119. Y.F. Xiao Cyclic AMP-dependent modulation of cardiac L-type Ca2+ and transient outward K+ channel activities by epoxyeicosatrienoic acids Prostaglandins Other Lipid Mediat. 82 2007 11 18
120. J. Seubert, B. Yang, J.A. Bradbury, J. Graves, L.M. Degraff, S. Gabel, R. Gooch, J. Foley, J. Newman, L. Mao, H.A. Rockman, B.D. Hammock, E. Murphy, and D.C. Zeldin Enhanced postischemic functional recovery in CYP2J2 transgenic hearts involves mitochondrial ATP-sensitive K+ channels and p42/p44 MAPK pathway Circ. Res. 95 2004 506 514
121. J.M. Seubert, D.C. Zeldin, K. Nithipatikom, and G.J. Gross Role of epoxyeicosatrienoic acids in protecting the myocardium following ischemia/reperfusion injury Prostaglandins Other Lipid Mediat. 82 2007 50 59
122. G.J. Gross, A. Hsu, J.R. Falck, and K. Nithipatikom Mechanisms by which epoxyeicosatrienoic acids (EETs) elicit cardioprotection in rat hearts J. Mol. Cell. Cardiol. 42 2007 687 691
123. I. Fleming Epoxyeicosatrienoic acids, cell signaling and angiogenesis Prostaglandins Other Lipid Mediat. 82 2007 60 67
124. A.A. Spector, and A.W. Norris Action of epoxyeicosatrienoic acids on cellular function Am. J. Physiol. Cell Physiol. 292 2007 C996 C1012
125. M. Medhora, A. Dhanasekaran, S.K. Gruenloh, L.K. Dunn, M. Gabrilovich, J.R. Falck, D.R. Harder, E.R. Jacobs, and P.F. Pratt Emerging mechanisms for growth and protection of the vasculature by cytochrome P450-derived products of arachidonic acid and other eicosanoids Prostaglandins Other Lipid Mediat. 82 2007 19 29
126. B.T. Larsen, W.B. Campbell, and D.D. Gutterman Beyond vasodilatation: non-vasomotor roles of epoxyeicosatrienoic acids in the cardiovascular system Trends Pharmacol. Sci. 28 2007 32 38
127. M. Spiecker, and J.K. Liao Vascular protective effects of cytochrome p450 epoxygenase-derived eicosanoids Arch. Biochem. Biophys. 433 2005 413 420
128. K. Node, Y. Huo, X. Ruan, B. Yang, M. Spiecker, K. Ley, D.C. Zeldin, and J.K. Liao Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids Science 285 1999 1276 1279
129. D. Xu, N. Li, Y. He, V. Timofeyev, L. Lu, H.J. Tsai, I.H. Kim, D. Tuteja, R.K. Mateo, A. Singapuri, B.B. Davis, R. Low, B.D. Hammock, and N. Chiamvimonvat Prevention and reversal of cardiac hypertrophy by soluble epoxide hydrolase inhibitors Proc. Natl. Acad. Sci. U. S. A. 103 2006 18733 18738
130. J.D. Imig Epoxide hydrolase and epoxygenase metabolites as therapeutic targets for renal diseases Am. J. Physiol. Renal Physiol. 289 2005 F496 F503
131. D.N. Muller, J. Theuer, E. Shagdarsuren, E. Kaergel, H. Honeck, J.K. Park, M. Markovic, E. Barbosa-Sicard, R. Dechend, M. Wellner, T. Kirsch, A. Fiebeler, M. Rothe, H. Haller, F.C. Luft, and W.H. Schunck A peroxisome proliferator-activated receptor-alpha activator induces renal CYP2C23 activity and protects from angiotensin II-induced renal injury Am. J. Pathol. 164 2004 521 532
132. E.L. Liclican, J.C. McGiff, J.R. Falck, and M.A. Carroll Failure to upregulate the adenosine2A receptor-epoxyeicosatrienoic acid pathway contributes to the development of hypertension in Dahl salt-sensitive rats Am. J. Physiol. Renal Physiol. 295 2008 F1696 F1704
133. C. Morisseau, and B.D. Hammock Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles Annu. Rev. Pharmacol. Toxicol. 45 2005 311 333
134. J.D. Imig, and B.D. Hammock Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases Nat. Rev. Drug Discov. 8 2009 794 805
135. D. Ai, Y. Fu, D. Guo, H. Tanaka, N. Wang, C. Tang, B.D. Hammock, J.Y. Shyy, and Y. Zhu Angiotensin II up-regulates soluble epoxide hydrolase in vascular endothelium in vitro and in vivo Proc. Natl. Acad. Sci. U. S. A. 104 2007 9018 9023
136. D. Ai, W. Pang, N. Li, M. Xu, P.D. Jones, J. Yang, Y. Zhang, N. Chiamvimonvat, J.Y. Shyy, B.D. Hammock, and Y. Zhu Soluble epoxide hydrolase plays an essential role in angiotensin II-induced cardiac hypertrophy Proc. Natl. Acad. Sci. U. S. A. 106 2009 564 569
137. J. Monti, J. Fischer, S. Paskas, M. Heinig, H. Schulz, C. Gosele, A. Heuser, R. Fischer, C. Schmidt, A. Schirdewan, V. Gross, O. Hummel, H. Maatz, G. Patone, K. Saar, M. Vingron, S.M. Weldon, K. Lindpaintner, B.D. Hammock, K. Rohde, R. Dietz, S.A. Cook, W.H. Schunck, F.C. Luft, and N. Hubner Soluble epoxide hydrolase is a susceptibility factor for heart failure in a rat model of human disease Nat. Genet. 40 2008 529 537
138. B. Inceoglu, K.R. Schmelzer, C. Morisseau, S.L. Jinks, and B.D. Hammock Soluble epoxide hydrolase inhibition reveals novel biological functions of epoxyeicosatrienoic acids EETs Prostaglandins Other Lipid Mediat. 82 2007 42 49
139. J.G. Jiang, Y.G. Ning, C. Chen, D. Ma, Z.J. Liu, S. Yang, J. Zhou, X. Xiao, X.A. Zhang, M.L. Edin, J.W. Card, J. Wang, D.C. Zeldin, and D.W. Wang Cytochrome p450 epoxygenase promotes human cancer metastasis Cancer Res. 67 2007 6665 6674
140. M.P. Hutchens, T. Nakano, J. Dunlap, R.J. Traystman, P.D. Hurn, and N.J. Alkayed Soluble epoxide hydrolase gene deletion reduces survival after cardiac arrest and cardiopulmonary resuscitation Resuscitation 76 2008 89 94
141. V. Mastyugin, E. Aversa, A. Bonazzi, C. Vafaes, P. Mieyal, and M.L. Schwartzman Hypoxia-induced production of 12-hydroxyeicosanoids in the corneal epithelium: involvement of a cytochrome P-4504B1 isoform J. Pharmacol. Exp. Ther. 289 1999 1611 1619
142. L. Du, V. Yermalitsky, D.L. Hachey, S.G. Jagadeesh, J.R. Falck, and D.S. Keeney A biosynthetic pathway generating 12-hydroxy-5,8,14-eicosatrienoic acid from arachidonic acid is active in mouse skin microsomes J. Pharmacol. Exp. Ther. 316 2006 371 379
143. M.F. Moghaddam, D.F. Grant, J.M. Cheek, J.F. Greene, K.C. Williamson, and B.D. Hammock Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase Nat. Med. 3 1997 562 566
144. A. Luria, S.M. Weldon, A.K. Kabcenell, R.H. Ingraham, D. Matera, H. Jiang, R. Gill, C. Morisseau, J.W. Newman, and B.D. Hammock Compensatory mechanism for homeostatic blood pressure regulation in Ephx2 gene-disrupted mice J. Biol. Chem. 282 2007 2891 2898
145. J.H. Moran, L.A. Mitchell, J.A. Bradbury, W. Qu, D.C. Zeldin, R.G. Schnellmann, and D.F. Grant Analysis of the cytotoxic properties of linoleic acid metabolites produced by renal and hepatic P450s Toxicol. Appl. Pharmacol. 168 2000 268 279
146. F. Adas, J.P. Salaun, F. Berthou, D. Picart, B. Simon, and Y. Amet Requirement for omega and (omega;-1)-hydroxylations of fatty acids by human cytochromes P450 2E1 and 4A11 J. Lipid Res. 40 1999 1990 1997
147. A.J. Draper, and B.D. Hammock Identification of CYP2C9 as a human liver microsomal linoleic acid epoxygenase Arch. Biochem. Biophys. 376 2000 199 205
148. L.M. King, J. Ma, S. Srettabunjong, J. Graves, J.A. Bradbury, L. Li, M. Spiecker, J.K. Liao, H. Mohrenweiser, and D.C. Zeldin Cloning of CYP2J2 gene and identification of functional polymorphisms Mol. Pharmacol. 61 2002 840 852 (Pubitemid 34273164)
149. H. Wang, Y. Zhao, J.A. Bradbury, J.P. Graves, J. Foley, J.A. Blaisdell, J.A. Goldstein, and D.C. Zeldin Cloning, expression, and characterization of three new mouse cytochrome p450 enzymes and partial characterization of their fatty acid oxidation activities Mol. Pharmacol. 65 2004 1148 1158
150. B.E. Daikh, R.M. Laethem, and D.R. Koop Stereoselective epoxidation of arachidonic acid by cytochrome P-450s 2CAA and 2C2 J. Pharmacol. Exp. Ther. 269 1994 1130 1135
151. R.M. Laethem, M. Balazy, and D.R. Koop Epoxidation of C18 unsaturated fatty acids by cytochromes P4502C2 and P4502CAA Drug Metab. Dispos. 24 1996 664 668
152. K. Kosaka, K. Suzuki, M. Hayakawa, S. Sugiyama, and T. Ozawa Leukotoxin, a linoleate epoxide: its implication in the late death of patients with extensive burns Mol. Cell. Biochem. 139 1994 141 148
153. T. Ozawa, S. Sugiyama, M. Hayakawa, T. Satake, F. Taki, M. Iwata, and K. Taki Existence of leukotoxin 9,10-epoxy-12-octadecenoate in lung lavages from rats breathing pure oxygen and from patients with the adult respiratory distress syndrome Am. Rev. Respir. Dis. 137 1988 535 540
154. T. Ozawa, M. Hayakawa, T. Takamura, S. Sugiyama, K. Suzuki, M. Iwata, F. Taki, and T. Tomita Biosynthesis of leukotoxin, 9,10-epoxy-12 octadecenoate, by leukocytes in lung lavages of rat after exposure to hyperoxia Biochem. Biophys. Res. Commun. 134 1986 1071 1078
155. M. Hayakawa, S. Sugiyama, T. Takamura, K. Yokoo, M. Iwata, K. Suzuki, F. Taki, S. Takahashi, and T. Ozawa Neutrophils biosynthesize leukotoxin, 9, 10-epoxy-12-octadecenoate Biochem. Biophys. Res. Commun. 137 1986 424 430
156. T. Ozawa, S. Sugiyama, M. Hayakawa, F. Taki, and Y. Hanaki Neutrophil microsomes biosynthesize linoleate epoxide (9,10-epoxy-12-octadecenoate), a biological active substance Biochem. Biophys. Res. Commun. 152 1988 1310 1318
157. M. Hayakawa, T. Ogawa, S. Sugiyama, and T. Ozawa Hydroxyl radical and leukotoxin biosynthesis in neutrophil plasma membrane Biochem. Biophys. Res. Commun. 161 1989 1077 1085
158. T. Sakai, T. Ishizaki, T. Ohnishi, F. Sasaki, S. Ameshima, T. Nakai, S. Miyabo, S. Matsukawa, M. Hayakawa, and T. Ozawa Leukotoxin, 9,10-epoxy-12- octadecenoate inhibits mitochondrial respiration of isolated perfused rat lung Am. J. Physiol. 269 1995 L326 L331
159. T. Ishizaki, K. Shigemori, T. Nakai, S. Miyabo, T. Ozawa, S.W. Chang, and N.F. Voelkel Leukotoxin, 9,10-epoxy-12-octadecenoate causes edematous lung injury via activation of vascular nitric oxide synthase Am. J. Physiol. 269 1995 L65 L70
160. T. Ishizaki, K. Shigemori, T. Nakai, S. Miyabo, M. Hayakawa, T. Ozawa, N.F. Voelkel, and S.W. Chang Endothelin-1 potentiates leukotoxin-induced edematous lung injury J. Appl. Physiol. 79 1995 1106 1111
161. J.N. Hu, F. Taki, S. Sugiyama, J. Asai, Y. Izawa, T. Satake, and T. Ozawa Neutrophil-derived epoxide, 9,10-epoxy-12-octadecenoate, induces pulmonary edema Lung 166 1988 327 337
162. S. Sugiyama, M. Hayakawa, S. Nagai, M. Ajioka, and T. Ozawa Leukotoxin, 9, 10-epoxy-12-octadecenoate, causes cardiac failure in dogs Life Sci. 40 1987 225 231
163. A. Fukushima, M. Hayakawa, S. Sugiyama, M. Ajioka, T. Ito, T. Satake, and T. Ozawa Cardiovascular effects of leukotoxin (9, 10-epoxy-12-octadecenoate) and free fatty acids in dogs Cardiovasc. Res. 22 1988 213 218
164. J. Zheng, C.G. Plopper, J. Lakritz, D.H. Storms, and B.D. Hammock Leukotoxin-diol: a putative toxic mediator involved in acute respiratory distress syndrome Am. J. Respir. Cell. Mol. Biol. 25 2001 434 438
165. J.H. Moran, R. Weise, R.G. Schnellmann, J.P. Freeman, and D.F. Grant Cytotoxicity of linoleic acid diols to renal proximal tubular cells Toxicol. Appl. Pharmacol. 146 1997 53 59
166. J.R. Stimers, M. Dobretsov, S.L. Hastings, A.R. Jude, and D.F. Grant Effects of linoleic acid metabolites on electrical activity in adult rat ventricular myocytes Biochim. Biophys. Acta 1438 1999 359 368
167. R. Slim, B.D. Hammock, M. Toborek, L.W. Robertson, J.W. Newman, C.H. Morisseau, B.A. Watkins, V. Saraswathi, and B. Hennig The role of methyl-linoleic acid epoxide and diol metabolites in the amplified toxicity of linoleic acid and polychlorinated biphenyls to vascular endothelial cells Toxicol. Appl. Pharmacol. 171 2001 184 193
168. S. Viswanathan, B.D. Hammock, J.W. Newman, P. Meerarani, M. Toborek, and B. Hennig Involvement of CYP 2C9 in mediating the proinflammatory effects of linoleic acid in vascular endothelial cells J. Am. Coll. Nutr. 22 2003 502 510
169. L.A. Mitchell, D.F. Grant, R.B. Melchert, N.M. Petty, and R.H. Kennedy Linoleic acid metabolites act to increase contractility in isolated rat heart Cardiovasc. Toxicol. 2 2002 219 230
170. G. Nowak, D.F. Grant, and J.H. Moran Linoleic acid epoxide promotes the maintenance of mitochondrial function and active Na+ transport following hypoxia Toxicol. Lett. 147 2004 161 175
171. L. Kubala, K.R. Schmelzer, A. Klinke, H. Kolarova, S. Baldus, B.D. Hammock, and J.P. Eiserich Modulation of arachidonic and linoleic acid metabolites in myeloperoxidase-deficient mice during acute inflammation Free Radic. Biol. Med. 48 2010 1131 1320
172. K.R. Smith, K.E. Pinkerton, T. Watanabe, T.L. Pedersen, S.J. Ma, and B.D. Hammock Attenuation of tobacco smoke-induced lung inflammation by treatment with a soluble epoxide hydrolase inhibitor Proc. Natl. Acad. Sci. U. S. A. 102 2005 2186 2191
173. X. Zhao, T. Yamamoto, J.W. Newman, I.H. Kim, T. Watanabe, B.D. Hammock, J. Stewart, J.S. Pollock, D.M. Pollock, and J.D. Imig Soluble epoxide hydrolase inhibition protects the kidney from hypertension-induced damage J. Am. Soc. Nephrol. 15 2004 1244 1253
174. J.W. Newman, T. Watanabe, and B.D. Hammock The simultaneous quantification of cytochrome P450 dependent linoleate and arachidonate metabolites in urine by HPLC-MS/MS J. Lipid Res. 43 2002 1563 1578
175. A.W. Dreisbach, J.C. Rice, S. Japa, J.W. Newman, A. Sigel, R.S. Gill, A.E. Hess, A.C. Cemo, J.P. Fonseca, B.D. Hammock, J.J. Lertora, and L.L. Hamm Salt loading increases urinary excretion of linoleic acid diols and triols in healthy human subjects Hypertension 51 2008 755 761
176. V.R. Holla, K. Makita, P.G. Zaphiropoulos, and J.H. Capdevila The kidney cytochrome P-450 2C23 arachidonic acid epoxygenase is upregulated during dietary salt loading J. Clin. Invest. 104 1999 751 760
177. E.L. Liclican, A.B. Doumad, J. Wang, J. Li, J.R. Falck, C.T. Stier Jr., and M.A. Carroll Inhibition of the adenosine2A receptor-epoxyeicosatrienoic acid pathway renders Dahl salt-resistant rats hypertensive Hypertension 54 2009 1284 1290
178. A. Ulu, B.B. Davis, H.J. Tsai, I.H. Kim, C. Morisseau, B. Inceoglu, O. Fiehn, B.D. Hammock, and R.H. Weiss Soluble epoxide hydrolase inhibitors reduce the development of atherosclerosis in apolipoprotein e-knockout mouse model J. Cardiovasc. Pharmacol. 52 2008 314 323
179. H. Sprecher, M. VanRollins, F. Sun, A. Wyche, and P. Needleman Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney J. Biol. Chem. 257 1982 3912 3918
180. C.J. Mann, T.L. Kaduce, P.H. Figard, and A.A. Spector Docosatetraenoic acid in endothelial cells: formation, retroconversion to arachidonic acid, and effect on prostacyclin production Arch. Biochem. Biophys. 244 1986 813 823
181. M. Martinez Abnormal profiles of polyunsaturated fatty acids in the brain, liver, kidney and retina of patients with peroxisomal disorders Brain Res. 583 1992 171 182
182. P.G. Kopf, D.X. Zhang, K.M. Gauthier, K. Nithipatikom, X.Y. Yi, J.R. Falck, and W.B. Campbell Adrenic acid metabolites as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors Hypertension 55 2010 547 554
183. X.Y. Yi, K.M. Gauthier, L. Cui, K. Nithipatikom, J.R. Falck, and W.B. Campbell Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo- epoxyeicosatrienoic acids by bovine coronary arteries Am. J. Physiol. Heart Circ. Physiol. 292 2007 H2265 H2274
184. Y. Zhang, C.L. Oltman, T. Lu, H.C. Lee, K.C. Dellsperger, and M. VanRollins EET homologs potently dilate coronary microvessels and activate BK(Ca) channels Am. J. Physiol. Heart Circ. Physiol. 280 2001 H2430 H2440
185. M. VanRollins, R.C. Baker, H.W. Sprecher, and R.C. Murphy Oxidation of docosahexaenoic acid by rat liver microsomes J. Biol. Chem. 259 1984 5776 5783
186. M. Van Rollins, P.D. Frade, and O.A. Carretero Oxidation of 5,8,11,14,17-eicosapentaenoic acid by hepatic and renal microsomes Biochim. Biophys. Acta 966 1988 133 149
187. B. Lauterbach, E. Barbosa-Sicard, M.H. Wang, H. Honeck, E. Kargel, J. Theuer, M.L. Schwartzman, H. Haller, F.C. Luft, M. Gollasch, and W.H. Schunck Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators Hypertension 39 2002 609 613
188. S.D. Harmon, X. Fang, T.L. Kaduce, S. Hu, V. Raj Gopal, J.R. Falck, and A.A. Spector Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production Prostaglandins Leukot. Essent. Fatty Acids 75 2006 169 177
189. S.S. Chuang, C. Helvig, M. Taimi, H.A. Ramshaw, A.H. Collop, M. Amad, J.A. White, M. Petkovich, G. Jones, and B. Korczak CYP2U1, a novel human thymus- and brain-specific cytochrome P450, catalyzes omega- and (omega-1)- hydroxylation of fatty acids J. Biol. Chem. 279 2004 6305 6314
190. M. Karlgren, M. Backlund, I. Johansson, M. Oscarson, and M. Ingelman-Sundberg Characterization and tissue distribution of a novel human cytochrome P450-CYP2U1 Biochem. Biophys. Res. Commun. 315 2004 679 685
191. D. Schwarz, P. Kisselev, A. Chernogolov, W.H. Schunck, and I. Roots Human CYP1A1 variants lead to differential eicosapentaenoic acid metabolite patterns Biochem. Biophys. Res. Commun. 336 2005 779 783
192. M. Fer, Y. Dreano, D. Lucas, L. Corcos, J.P. Salaun, F. Berthou, and Y. Amet Metabolism of eicosapentaenoic and docosahexaenoic acids by recombinant human cytochromes P450 Arch. Biochem. Biophys. 471 2008 116 125
193. D. Lucas, S. Goulitquer, J. Marienhagen, M. Fer, Y. Dreano, U. Schwaneberg, Y. Amet, and L. Corcos Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450 J. Lipid Res. 51 2002 1125 1133
194. C. Arnold, M. Markovic, K. Blossey, G. Wallukat, R. Fischer, R. Dechend, A. Konkel, C. von Schacky, F.C. Luft, D.N. Muller, M. Rothe, and W.H. Schunck Arachidonic acid-metabolizing cytochrome P450 enzymes are targets of omega-3 fatty acids J. Biol. Chem. 2010 Sep 22, Epub ahead of print
195. K. Stark, B. Wongsud, R. Burman, and E.H. Oliw Oxygenation of polyunsaturated long chain fatty acids by recombinant CYP4F8 and CYP4F12 and catalytic importance of Tyr-125 and Gly-328 of CYP4F8 Arch. Biochem. Biophys. 441 2005 174 181
196. E. Barbosa-Sicard, M. Markovic, H. Honeck, B. Christ, D.N. Muller, and W.H. Schunck Eicosapentaenoic acid metabolism by cytochrome P450 enzymes of the CYP2C subfamily Biochem. Biophys. Res. Commun. 329 2005 1275 1281
197. H.R. Knapp, A.J. Miller, and J.A. Lawson Urinary excretion of diols derived from eicosapentaenoic acid during n-3 fatty acid ingestion by man Prostaglandins 42 1991 47 54
198. G.C. Shearer, W.S. Harris, T.L. Pedersen, and J.W. Newman Detection of omega-3 oxylipins in human plasma and response to treatment with omega-3 acid ethyl esters J. Lipid Res. 51 2010 2074 2081
199. H.C. Hercule, B. Salanova, K. Essin, H. Honeck, J.R. Falck, M. Sausbier, P. Ruth, W.H. Schunck, F.C. Luft, and M. Gollasch The vasodilator 17,18-epoxyeicosatetraenoic acid targets the pore-forming BK alpha channel subunit in rodents Exp. Physiol. 92 2007 1067 1076
200. D. Ye, D. Zhang, C. Oltman, K. Dellsperger, H.C. Lee, and M. VanRollins Cytochrome p-450 epoxygenase metabolites of docosahexaenoate potently dilate coronary arterioles by activating large-conductance calcium-activated potassium channels J. Pharmacol. Exp. Ther. 303 2002 768 776
201. T. Lu, M. VanRollins, and H.C. Lee Stereospecific activation of cardiac ATP-sensitive K(+) channels by epoxyeicosatrienoic acids: a structural determinant study Mol. Pharmacol. 62 2002 1076 1083
202. C. Morin, M. Sirois, V. Echave, E. Rizcallah, and E. Rousseau Relaxing effects of 17(18)-EpETE on arterial and airway smooth muscles in human lung Am. J. Physiol. Lung Cell. Mol. Physiol. 296 2009 L130 L139
203. C. Morin, M. Sirois, V. Echave, R. Albadine, E. Rousseau, 17,18-EpETE targets PPAR {gamma} and p38MAPK to mediate its anti-inflammatory effect in lung: role of sEH, Am. J. Respir. Cell Mol. Biol. Epub ahead of print.
204. L.A. Cowart, S. Wei, M.H. Hsu, E.F. Johnson, M.U. Krishna, J.R. Falck, and J.H. Capdevila The CYP4A isoforms hydroxylate epoxyeicosatrienoic acids to form high affinity peroxisome proliferator-activated receptor ligands J. Biol. Chem. 277 2002 35105 35112
205. V.Y. Ng, Y. Huang, L.M. Reddy, J.R. Falck, E.T. Lin, and D.L. Kroetz Cytochrome P450 eicosanoids are activators of peroxisome proliferator-activated receptor alpha Drug Metab. Dispos. 35 2007 1126 1134
206. Y. Liu, Y. Zhang, K. Schmelzer, T.S. Lee, X. Fang, Y. Zhu, A.A. Spector, S. Gill, C. Morisseau, B.D. Hammock, and J.Y. Shyy The antiinflammatory effect of laminar flow: the role of PPARgamma, epoxyeicosatrienoic acids, and soluble epoxide hydrolase Proc. Natl. Acad. Sci. U. S. A. 102 2005 16747 16752
207. X. Fang, S. Hu, B. Xu, G.D. Snyder, S. Harmon, J. Yao, Y. Liu, B. Sangras, J.R. Falck, N.L. Weintraub, and A.A. Spector 14,15- Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor-alpha Am. J. Physiol. Heart Circ. Physiol. 290 2006 H55 H63
208. J.A. Wray, M.C. Sugden, D.C. Zeldin, G.K. Greenwood, S. Samsuddin, L. Miller-Degraff, J.A. Bradbury, M.J. Holness, T.D. Warner, and D. Bishop-Bailey The epoxygenases CYP2J2 activates the nuclear receptor PPARalpha in vitro and in vivo PLoS One 4 2009 e7421
209. J. Wray, and D. Bishop-Bailey Epoxygenases and peroxisome proliferator-activated receptors in mammalian vascular biology Exp. Physiol. 93 2008 148 154
210. P.L. Li, and W.B. Campbell Epoxyeicosatrienoic acids activate K+ channels in coronary smooth muscle through a guanine nucleotide binding protein Circ. Res. 80 1997 877 884
211. K. Node, X.L. Ruan, J. Dai, S.X. Yang, L. Graham, D.C. Zeldin, and J.K. Liao Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids J. Biol. Chem. 276 2001 15983 15989
212. W. Yang, V.R. Tuniki, S. Anjaiah, J.R. Falck, C.J. Hillard, and W.B. Campbell Characterization of epoxyeicosatrienoic acid binding site in U937 membranes using a novel radiolabeled agonist, 20-125i-14,15-epoxyeicosa-8(Z)- enoic acid J. Pharmacol. Exp. Ther. 324 2008 1019 1027
213. Y. Chen, J.R. Falck, V.R. Tuniki, and W.B. Campbell 20-125Iodo-14,15- epoxyeicosa-5(Z)-enoic acid: a high-affinity radioligand used to characterize the epoxyeicosatrienoic acid antagonist binding site J. Pharmacol. Exp. Ther. 331 2009 1137 1145