Anti-inflammatory effects of epoxyeicosatrienoic acids

International Journal of Vascular Medicine

Volumn 2012, Issue , 2012, Pages

  Thomson, Scott J ^a   Askari, Ara ^a   Bishop Bailey, David ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONIC ACID; EPOXIDE HYDROLASE; EPOXYICOSATRIENOIC ACID; G PROTEIN COUPLED RECEPTOR; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; TRANSIENT RECEPTOR POTENTIAL CHANNEL;

ANGIOGENESIS; ANTIINFLAMMATORY ACTIVITY; ARACHIDONIC ACID METABOLISM; BLOOD VESSEL TONE; CELL MIGRATION; CELL PROLIFERATION; HUMAN; NONHUMAN; REVIEW; SIGNAL TRANSDUCTION; SMOOTH MUSCLE FIBER;

EID: 84866148838     PISSN: 20902824     EISSN: 20902832     Source Type: Journal    
DOI: 10.1155/2012/605101     Document Type: Review

References (65)

1. Leonarduzzi G., Gamba P., Gargiulo S., Biasi F., Poli G., Inflammation-related gene expression by lipid oxidation-derived products in the progression of atherosclerosis. Free Radical Biology and Medicine 52 1 19 34
2. He P., Leucocyte/endothelium interactions and microvessel permeability: coupled or uncoupled? Cardiovascular Research 2010 87 2 281 290 2-s2.0-77954331063 10.1093/cvr/cvq140
3. Wong C. H. Y., Heit B., Kubes P., Molecular regulators of leucocyte chemotaxis during inflammation. Cardiovascular Research 2010 86 2 183 191 2-s2.0-77951690581 10.1093/cvr/cvq040
4. Libby P., Sukhova G., Lee R. T., Galis Z. S., Cytokines regulate vascular functions related to stability of the atherosclerotic plaque. Journal of Cardiovascular Pharmacology 1995 25 supplement 2 S9 S12 2-s2.0-0029549156 (Pubitemid 26084648)
5. Capdevila J., Chacos N., Werringloer J., Liver microsomal cytochrome P-450 and the oxidative metabolism of arachidonic acid. Proceedings of the National Academy of Sciences of the United States of America 1981 78 9 5362 5366 2-s2.0-0344935682 (Pubitemid 12248586)
6. Oliw E. H., Oates J. A., Oxygenation of arachidonic acid by hepatic microsomes of the rabbit; mechanism of biosynthesis of two vicinal dihydroxyeicosatrienoic acids. Biochimica et Biophysica Acta 1981 666 3 327 340 2-s2.0-0019770983 (Pubitemid 12144864)
7. Oliw E. H., Moldeus P., Metabolism of arachidonic acid by isolated rat hepatocytes, renal cells and by some rabbit tissues. Detection of vicinal diols by mass fragmentography. Biochimica et Biophysica Acta 1982 721 2 135 143 2-s2.0-0020442370 (Pubitemid 13208552)
8. Capdevila J., Chacos N., Falck J. R., Novel hypothalamic arachidonate products stimulate somatostatin release from the median eminence. Endocrinology 1983 113 1 421 423 2-s2.0-0020510129 (Pubitemid 13045172)
9. Capdevila J., Snijder G. D., Falck J. R., Epoxygenation of arachidonic acid by rat anterior pituitary microsomal fractions. FEBS Letters 1984 178 2 319 322 2-s2.0-0021709546 10.1016/0014-5793(84)80625-0 (Pubitemid 15199597)
10. Nelson D. R., Zeldin D. C., Hoffman S. M. G., Maltais L. J., Wain H. M., Nebert D. W., Comparison of cytochrome P450 (CYP) genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternative-splice variants. Pharmacogenetics 2004 14 1 1 18 2-s2.0-0842312531 10.1097/00008571-200401000-00001 (Pubitemid 38183957)
11. Peter Guengerich F., Cheng Q., Orphans in the human cytochrome P450 superfamily: approaches to discovering functions and relevance in pharmacology. Pharmacological Reviews 2011 63 3 684 699 2-s2.0-79960657926 10.1124/pr.110.003525
12. Daikh B. E., Lasker J. M., Raucy J. L., Koop D. R., Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9. Journal of Pharmacology and Experimental Therapeutics 1994 271 3 1427 1433 2-s2.0-0027940480 (Pubitemid 24382654)
13. Wu S., Moomaw C. R., Tomer K. B., Falck J. R., Zeldin D. C., Molecular cloning and expression of CYP2J2, a human cytochrome P450 arachidonic acid epoxygenase highly expressed in heart. The Journal of Biological Chemistry 1996 271 7 3460 3468 2-s2.0-0030063499 10.1074/jbc.271.7.3460 (Pubitemid 26065653)
14. Gaedigk A., Baker D. W., Totah R. A., Gaedigk R., Pearce R. E., Vyhlidal C. A., Zeldin D. C., Leeder J. S., Variability of CYP2J2 expression in human fetal tissues. Journal of Pharmacology and Experimental Therapeutics 2006 319 2 523 532 2-s2.0-33751191888 10.1124/jpet.106.109215
15. Rifkind A. B., Lee C., Chang T. K. H., Waxman D. J., 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. Archives of Biochemistry and Biophysics 1995 320 2 380 389 2-s2.0-0029039791
16. Mitra R., Guo Z., Milani M., Mesaros C., Rodriguez M., Nguyen J., Luo X., Clarke D., Lamba J., Schuetz E., Donner D. B., Puli N., Falck J. R., Capdevila J., Gupta K., Blair I. A., Potter D. A., CYP3A4 mediates growth of estrogen receptor-positive breast cancer cells in part by inducing nuclear translocation of phospho-Stat3 through biosynthesis of (±)-14,15-epoxyeicosatrienoic acid (EET). The Journal of Biological Chemistry 2011 286 20 17543 17559 2-s2.0-79955947190 10.1074/jbc.M110.198515
17. Capdevila J. H., Karara A., Waxman D. J., Martin M. V., Falck J. R., Guenguerich F. P., Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase. The Journal of Biological Chemistry 1990 265 19 10865 10871 2-s2.0-0025311273
18. Keeney D. S., Skinner C., Wei S., Friedberg T., Waterman M. R., A keratinocyte-specific epoxygenase, CYP2B12, metabolizes arachidonic acid with unusual selectivity, producing a single major epoxyeicosatrienoic acid. The Journal of Biological Chemistry 1998 273 15 9279 9284 2-s2.0-0032502795 10.1074/jbc.273.15.9279 (Pubitemid 28176221)
19. Thompson C. M., Capdevila J. H., Strobel H. W., Recombinant cytochrome P450 2D18 metabolism of dopamine and arachidonic acid. Journal of Pharmacology and Experimental Therapeutics 2000 294 3 1120 1130 2-s2.0-0033846716 (Pubitemid 30666868)
20. Oleksiak M. F., Wu S., Parker C., Karchner S. I., Stegeman J. J., Zeldin D. C., Identification, functional characterization, and regulation of a new cytochrome P450 subfamily, the CYP2Ns. The Journal of Biological Chemistry 2000 275 4 2312 2321 2-s2.0-0034723401 10.1074/jbc.275.4.2312 (Pubitemid 30081987)
21. Nguyen X., Wang M. H., Reddy K. M., Falck J. R., Schwartzman M. L., Kinetic profile of the rat CYP4A isoforms: arachidonic acid metabolism and isoform-specific inhibitors. American Journal of Physiology 1999 276 6, part 2 R1691 R1700 2-s2.0-0032997280 (Pubitemid 29323534)
22. Imig J. D., Epoxides and soluble epoxide hydrolase in cardiovascular physiology. Physiological Reviews 92 1 101 130
23. Larsen B. T., Miura H., Hatoum O. A., Campbell W. B., Hammock B. D., Zeldin D. C., Falck J. R., Gutterman D. D., Epoxyeicosatrienoic and dihydroxyeicosatrienoic acids dilate human coronary arterioles via BKCa channels: implications for soluble epoxide hydrolase inhibition. American Journal of Physiology 2006 290 2 H491 H499 2-s2.0-33644849675 10.1152/ajpheart.00927.2005
24. Spector A. A., Fang X., Snyder G. D., Weintraub N. L., Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function. Progress in Lipid Research 2004 43 1 55 90 2-s2.0-0242720683 10.1016/S0163-7827(03)00049- 3 (Pubitemid 37433867)
25. Imig J. D., Eicosanoid regulation of the renal vasculature. American Journal of Physiology 2000 279 6 F965 F981 2-s2.0-0034534288 (Pubitemid 32001618)
26. Weintraub N. L., Fang X., Kaduce T. L., VanRollins M., Chatterjee P., Spector A. A., Epoxide hydrolases regulate epoxyeicosatrienoic acid incorporation into coronary endothelial phospholipids. American Journal of Physiology 1999 277 5, part 2 H2098 H2108 2-s2.0-0032735546
27. Zhang D., Xie X., Chen Y., Hammock B. D., Kong W., Zhu Y., Homocysteine upregulates soluble epoxide hydrolase in vascular endothelium in vitro and in vivo. Circulation Research 110 6 808 817 10.1161/CIRCRESAHA.111.259325
28. Revermann M., Schloss M., Barbosa-Sicard E., Mieth A., Liebner S., Morisseau C., Geisslinger G., Schermuly R. T., Fleming I., Hammock B. D., Brandes R. P., Soluble epoxide hydrolase deficiency attenuates neointima formation in the femoral cuff model of hyperlipidemic mice. Arteriosclerosis, Thrombosis, and Vascular Biology 2010 30 5 909 914 2-s2.0-77951498924 10.1161/ATVBAHA.110.204099
29. Zhang L. N., Vincelette J., Cheng Y., Mehra U., Chen D., Anandan S. K., Gless R., Webb H. K., Wang Y. X., Inhibition of soluble epoxide hydrolase attenuated atherosclerosis, abdominal aortic aneurysm formation, and dyslipidemia. Arteriosclerosis, Thrombosis, and Vascular Biology 2009 29 9 1265 1270 2-s2.0-69849107198 10.1161/ATVBAHA.109.186064
30. Lee C. R., Imig J. D., Edin M. L., Foley J., DeGraff L. M., Bradbury J. A., Graves J. P., Lih F. B., Clark J., Myers P., Perrow A. L., Lepp A. N., Kannon M. A., Ronnekleiv O. K., Alkayed N. J., Falck J. R., Tomer K. B., Zeldin D. C., Endothelial expression of human cytochrome P450 epoxygenases lowers blood pressure and attenuates hypertension-induced renal injury in mice. The FASEB Journal 2010 24 10 3770 3781 2-s2.0-77957831701 10.1096/fj.10-160119
31. Luo P., Chang H. H., Zhou Y., Zhang S., Hwang S. H., Morisseau C., Wang C. Y., Inscho E. W., Hammock B. D., Wang M. H., Inhibition or deletion of soluble epoxide hydrolase prevents hyperglycemia, promotes insulin secretion, and reduces islet apoptosis. Journal of Pharmacology and Experimental Therapeutics 2010 334 2 430 438 2-s2.0-77954902049 10.1124/jpet.110.167544
32. Fissithaler B., Popp R., Kiss L., Potente M., Harder D. R., Fleming I., Busse R., Cytochrome P450 2C is an EDHF synthasein coronary arteries. Nature 1999 401 6752 493 497 2-s2.0-0033619262 10.1038/46816 (Pubitemid 29470209)
33. Fisslthaler B., Fleming I., Busse R., EDHF: a cytochrome P450 metabolite in coronary arteries. Seminars in Perinatology 2000 24 1 15 19 2-s2.0-0034007090 (Pubitemid 30115264)
34. Bystrom J., Wray J. A., Sugden M. C., Endogenous epoxygenases are modulators of monocyte/macrophage activity. PLoS ONE 2011 6 10 e26591 10.1371/journal.pone.0026591
35. Node K., Huo Y., Ruan X., Yang B., Spiecker M., Ley K., Zeldin D. C., Liao J. K., Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science 1999 285 5431 1276 1279 2-s2.0-0033588034 10.1126/science.285.5431.1276 (Pubitemid 29398616)
36. Nakayama K., Nitto T., Inoue T., Node K., Expression of the cytochrome P450 epoxygenase CYP2J2 in human monocytic leukocytes. Life Sciences 2008 83 9-10 339 345 2-s2.0-49549112885 10.1016/j.lfs.2008.06.026
37. Spiecker M., Darius H., Hankeln T., Soufi M., Sattler A. M., Schaefer J. R., Node K., Börgel J., Mügge A., Lindpaintner K., Huesing A., Maisch B., Zeldin D. C., Liao J. K., Risk of coronary artery disease associated with polymorphism of the cytochrome P450 epoxygenase CYP2J2. Circulation 2004 110 15 2132 2136 2-s2.0-20844452556 10.1161/01.CIR.0000143832.91812.60 (Pubitemid 39372490)
38. Michaelis U. R., Fisslthaler B., Medhora M., Harder D., Fleming I., Busse R., Cytochrome P450 2C9-derived epoxyeicosatrienoic acids induce angiogenesis via cross-talk with the epidermal growth factor receptor (EGFR). The FASEB Journal 2003 17 6 770 772 2-s2.0-0037387681
39. Zhao G., Tu L., Li X., Delivery of AAV2-CYP2J2 protects remnant kidney in the 5/6-nephrectomized rat via inhibition of apoptosis andfibrosis. Human Gene Therapy. In press 10.1089/hum.2011.135
40. Deng Y., Edin M. L., Theken K. N., Schuck R. N., Flake G. P., Kannon M. A., DeGraff L. M., Lih F. B., Foley J., Bradbury J. A., Graves J. P., Tomer K. B., Falck J. R., Zeldin D. C., Lee C. R., Endothelial CYP epoxygenase overexpression and soluble epoxide hydrolase disruption attenuate acute vascular inflammatory responses in mice. The FASEB Journal 2011 25 2 703 713 2-s2.0-79551646708 10.1096/fj.10-171488
41. Kozak W., Aronoff D. M., Boutaud O., Kozak A., 11,12-Epoxyeicosatrienoic acid attenuates synthesis of prostaglandin E2 in rat monocytes stimulated with lipopolysaccharide. Experimental Biology and Medicine 2003 228 7 786 794 2-s2.0-0141567962 (Pubitemid 37169263)
42. Werner K., Schaefer W. R., Schweer H., Deppert W. R., Karck U., Zahradnik H. P., Characterization and identification of cytochrome P450 metabolites of arachidonic acid released by human peritoneal macrophages obtained from the pouch of Douglas. Prostaglandins Leukotrienes and Essential Fatty Acids 2002 67 6 397 404 2-s2.0-0036892329 10.1054/plef.2002.0449 (Pubitemid 35398900)
43. Pritchard K. A. Jr., Tota R. R., Stemerman M. B., Wong P. Y. K., 14,15-Epoxyeicosatrienoic acid promotes endothelial cell dependent adhesion of human monocytic tumor U937 cells. Biochemical and Biophysical Research Communications 1990 167 1 137 142 2-s2.0-0025253159 10.1016/0006-291X(90)91741-A (Pubitemid 20085360)
44. Pratt P. F., Rosolowsky M., Campbell W. B., Effects of epoxyeicosatrienoic acids on polymorphonuclear leukocyte function. Life Sciences 2002 70 21 2521 2533 2-s2.0-0037066413 10.1016/S0024-3205(02)01533-3 (Pubitemid 34267040)
45. Morin C., Sirois M., Echave V., Gomes M. M., Rousseau E., EET displays anti-inflammatory effects in TNF stimulated human bronchi: putative role of CPI-17. American Journal of Respiratory Cell and Molecular Biology 2008 38 2 192 201 2-s2.0-38549155981 10.1165/rcmb.2007-0232OC (Pubitemid 351162841)
46. Fife K. L., Liu Y., Schmelzer K. R., Tsai H. J., Kim I. H., Morisseau C., Hammock B. D., Kroetz D. L., Inhibition of soluble epoxide hydrolase does not protect against endotoxin-mediated hepatic inflammation. Journal of Pharmacology and Experimental Therapeutics 2008 327 3 707 715 2-s2.0-57349120615 10.1124/jpet.108.142398
47. Hayden M. S., Ghosh S., Shared principles in NB signaling. Cell 2008 132 3 344 362 2-s2.0-38849199203 10.1016/j.cell.2008.01.020 (Pubitemid 351192002)
48. Hayden M. S., Ghosh S., NF- κ B, the first quarter-century: remarkable progress and outstanding questions. Genes & Development 2012 26 3 203 234
49. Fleming I., Michaelis U. R., Bredenkötter D., Fisslthaler B., Dehghani F., Brandes R. P., Busse R., Endothelium-derived hyperpolarizing factor synthase (cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries. Circulation Research 2001 88 1 44 51 2-s2.0-0035910620 (Pubitemid 32064081)
50. Williams L., Bradley L., Smith A., Foxwell B., Signal transducer and activator of transcription 3 is the dominant mediator of the anti-inflammatory effects of IL-10 in human macrophages. Journal of Immunology 2004 172 1 567 576 2-s2.0-0346103717 (Pubitemid 38020514)
51. Berger J., Moller D. E., The mechanisms of action of PPARs. Annual Review of Medicine 2002 53 409 435 2-s2.0-0036183630 10.1146/annurev.med.53.082901. 104018 (Pubitemid 34177889)
52. Cowart L. A., Wei S., Hsu M. H., Johnson E. F., Krishna M. U., Falck J. R., Capdevila J. H., The CYP4A isoforms hydroxylate epoxyeicosatrienoic acids to form high affinity peroxisome proliferator-activated receptor ligands. The Journal of Biological Chemistry 2002 277 38 35105 35112 2-s2.0-0037144475 10.1074/jbc.M201575200
53. Wray J. A., Sugden M. C., Zeldin D. C., Greenwood G. K., Samsuddin S., Miller-Degraff L., Bradbury J. A., Holness M. J., Warner T. D., Bishop-Bailey D., The epoxygenases CYP2J2 activates the nuclear receptor PPAR α in vitro and in vivo. PLoS ONE 2009 4 10 2-s2.0-70350540660 10.1371/journal.pone.0007421 e7421
54. Liu Y., Zhang Y., Schmelzer K., Lee T. S., Fang X., Zhu Y., Spector A. A., Gill S., Morisseau C., Hammock B. D., Shyy J. Y. J., The antiinflammatory effect of laminar flow: the role of PPAR γ epoxyeicosatrienoic acids, and soluble epoxide hydrolase. Proceedings of the National Academy of Sciences of the United States of America 2005 102 46 16747 16752 2-s2.0-28044434102 10.1073/pnas.0508081102 (Pubitemid 41688848)
55. Fang X., Hu S., Xu B., Snyder G. D., Harmon S., Yao J., Liu Y., Sangras B., Falck J. R., Weintraub N. L., Spector A. A., 14,15-Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor- α American Journal of Physiology 2006 290 1 H55 H63 2-s2.0-33644790290 10.1152/ajpheart. 00427.2005
56. Olearczyk J. J., Field M. B., Kim I. H., Morisseau C., Hammock B. D., Imig J. D., Substituted adamantyl-urea inhibitors of the soluble epoxide hydrolase dilate mesenteric resistance vessels. Journal of Pharmacology and Experimental Therapeutics 2006 318 3 1307 1314 2-s2.0-33747611948 10.1124/jpet.106.103556 (Pubitemid 44268340)
57. + channels in coronary smooth muscle through a guanine nucleotide binding protein. Circulation Research 1997 80 6 877 884 2-s2.0-0030973315 (Pubitemid 27230063)
58. Wong P. Y. K., Lin K. T., Yan Y. T., Ahern D., Iles J., Shen S. Y., Bhatt R. K., Falck J. R., 14(R),15(S)-epoxyeicosatrienoic acid (14(R),15(S)-EET) receptor in guinea pig mononuclear cell membranes. Journal of Lipid Mediators 1992 6 13 199 208 2-s2.0-0026989776 (Pubitemid 23152450)
59. Watanabe H., Vriens J., Prenen J., Droogmans G., Voets T., Nillus B., Anandamide and arachidonic acid use epoxyeicosatrienoic acids to activate TRPV4 channels. Nature 2003 424 6947 434 438 2-s2.0-0043267987 10.1038/nature01807 (Pubitemid 36917492)
60. 2+ signaling complex with ryanodine receptors and BKCa channels. Circulation Research 2005 97 12 1270 1279 2-s2.0-33644671418 10.1161/01.RES.0000194321.60300.d6
61. 2+ permeable cation channel TRPV4 by cytochrome P450 epoxygenases in vascular endothelium. Circulation Research 2005 97 9 908 915 2-s2.0-27644497526 10.1161/01.RES.0000187474.47805.30 (Pubitemid 41552676)
62. Baylie R. L., Brayden J. E., TRPV channels and vascular function. Acta Physiologica 203 1 99 116
63. Buczynski M. W., Dumlao D. S., Dennis E. A., An integrated omics analysis of eicosanoid biology. Journal of Lipid Research 2009 50 6 1015 1038 2-s2.0-67650531422 10.1194/jlr.R900004-JLR200
64. Theken K. N., Schuck R. N., Edin M. L., Evaluation of cytochrome P450-derived eicosanoids in humans with stable atherosclerotic cardiovascular disease. Atherosclerosis 222 2 530 536
65. Morin C., Sirois M., Echave V., Rizcallah E., Rousseau E., Relaxing effects of 17(18)-EpETE on arterial and airway smooth muscles in human lung. American Journal of Physiology 2009 296 1 L130 L139 2-s2.0-58149529357 10.1152/ajplung.90436.2008