Epoxyeicosatrienoic acids, cell signaling and angiogenesis

Prostaglandins and Other Lipid Mediators

Volumn 82, Issue 1-4, 2007, Pages 60-67

  Fleming, Ingrid ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

Angiogenesis; Ca2+ dependent K+ channels; Cytochrome P450; Eiciosanoids; Endothelium; Signal transduction

Indexed keywords

CYTOCHROME P450; EPOXYICOSATRIENOIC ACID;

ANGIOGENESIS; CELL PROLIFERATION; ENZYME ACTIVATION; NONHUMAN; PROTEIN EXPRESSION; REVIEW; VASODILATATION;

8,11,14-EICOSATRIENOIC ACID; CELL PROLIFERATION; CYTOCHROME P-450 ENZYME SYSTEM; ENDOTHELIAL CELLS; EPOXY COMPOUNDS; NEOVASCULARIZATION, PHYSIOLOGIC; OXYGENASES; SIGNAL TRANSDUCTION;

EID: 33845346159     PISSN: 10988823     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.prostaglandins.2006.05.003     Document Type: Review

References (66)

1. Campbell W.B., Gebremedhin D., Pratt P.F., and Harder D.R. Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors. Circ Res 78 (1996) 415-423
2. Fisslthaler B., Popp R., Kiss L., et al. Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature 401 (1999) 493-497
3. Fisslthaler B., Hinsch N., Chataigneau T., et al. Nifedipine increases cytochrome P4502C expression and EDHF-mediated responses in coronary arteries. Hypertension 36 (2000) 270-275
4. Fisslthaler B., Popp R., Michaelis U.R., et al. Cyclic stretch enhances the expression and activity of coronary endothelium-derived hyperpolarizing factor synthase. Hypertension 38 (2001) 1427-1432
5. Gerbal-Chaloin S., Pascussi J.M., Pichard-Garcia L., et al. Induction of CYP2C genes in human hepatocytes in primary culture. Drug Metab Dispos 29 (2001) 242-251
6. Gerbal-Chaloin S., Daujat M., Pascussi J.M., et al. Transcriptional Regulation of CYP2C9 Gene. Role of glucocorticoid receptor and constitutive androstane receptor. J Biol Chem 277 (2002) 209-217
7. de Morais S.M.F., Schweikl H., Blaisdell J., and Goldstein J.A. Gene structure and upstream regulatory regions of human CYP2C9 and CYP2C18. Biochem Biophys Res Commun 194 (1993) 194-201
8. Ged C., and Beaune P. Isolation of the human cytochrome P-450 IIC8 gene: multiple glucocorticoid responsive elements in the 5' region. Biochim Biophys Acta 1088 (1991) 433-435
9. Bauersachs J., Christ M., Ertl G., et al. Cytochrome P450 2C expression and EDHF-mediated relaxation in porcine coronary arteries is increased by cortisol. Cardiovasc Res 54 (2002) 669-675
10. Transon C., Leemann T., and Dayer P. In vitro comparative inhibition profiles of major human drug metabolising cytochrome P450 isozymes (CYP2C9, CYP2D6 and CYP3A4) by HMG-CoA reductase inhibitors. Eur J Clin Pharmacol 50 (1996) 209-215
11. Fischer V., Johanson L., Heitz F., et al. The 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor fluvastatin: effect on human cytochrome P-450 and implications for metabolic drug interactions. Drug Metab Dispos 27 (1999) 410-416
12. Qiu W.P., Hu Q., Paolocci N., Ziegelstein R.C., and Kass D.A. Differential effects of pulsatile versus steady flow on coronary endothelial membrane potential. Am J Physiol Heart Circ Physiol 285 (2003) H341-H346
13. Marden N.Y., Fiala-Beer E., Xiang S.H., and Murray M. Role of activator protein-1 in the down-regulation of the human CYP2J2 gene in hypoxia. Biochem J 373 (2003) 669-680
14. Michaelis U.R., Fisslthaler B., Barbosa-Sicard E., et al. Cytochrome P450 epoxygenases 2C8 and 2C9 are implicated in hypoxia-induced endothelial cell migration and angiogenesis. J Cell Sci 118 (2005) 5489-5498
15. Pokreisz P., Fleming I., Kiss L., et al. Cytochrome P450 epoxygenase gene function in hypoxic pulmonary vasoconstriction and pulmonary vascular remodeling. Hypertension 47 (2006) 762-770
16. Alkayed N.J., Goyagi T., Joh H.D., et al. Neuroprotection and P450 2C11 upregulation after experimental transient ischemic attack. Stroke 33 (2002) 1677-1684
17. Earley S., and Walker B.R. Endothelium-dependent blunting of myogenic responsiveness after chronic hypoxia. Am J Physiol Heart Circ Physiol 283 (2002) H2202-H2209
18. Earley S., Pastuszyn A., and Walker B.R. Cytochrome P-450 epoxygenase products contribute to attenuated vasoconstriction after chronic hypoxia. Am J Physiol Heart Circ Physiol 285 (2003) H127-H136
19. Oesch-Bartlomowicz B., Richter B., Becker R., et al. cAMP-dependent phosphorylation of CYP2B1 as a functional switch for cyclophosphamide activation and its hormonal control in vitro and in vivo. Int J Cancer 94 (2001) 733-742
20. Korsmeyer K.K., Davoll S., Figueiredo-Pereira M.E., and Correia M.A. Proteolytic degradation of heme-modified hepatic cytochromes P450: A role for phosphorylation, ubiquitination, and the 26S proteasome?. Arch Biochem Biophys 365 (1999) 31-44
21. Anandatheerthavarada H.K., Biswas G., Mullick J., et al. Dual targeting of cytochrome P4502B1 to endoplasmic reticulum and mitochondria involves a novel signal activation by cyclic AMP-dependent phosphorylation at Ser128. EMBO J 18 (1999) 5494-5504
22. Eliasson E., Mkrtchian S., and Ingelman-Sundberg M. Hormone- and substrate-regulated intracellular degradation of cytochrome P450 (2E1) involving MgATP-activated rapid proteolysis in the endoplasmic reticulum membranes. J Biol Chem 267 (1992) 15765-15769
23. Wong P.Y., Lai P.S., and Falck J.R. Mechanism and signal transduction of 14 (R), 15 (S)-epoxyeicosatrienoic acid (14,15-EET) binding in guinea pig monocytes. Prostaglandins Other Lipid Mediat 62 (2000) 321-333
24. + channels in coronary smooth muscle through a guanine nucleotide binding protein. Circ Res 80 (1997) 877-884
25. Capdevila J.H., Falck J.R., and Harris R.C. Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase. J Lipid Res 41 (2000) 163-181
26. Ca channels expressed in human embryonic kidney 293 cells by epoxyeicosatrienoic acid. Mol Pharmacol 59 (2001) 16-23
27. Imig J.D., Inscho E.W., Deichamnn P.C., Reddy K.M., and Falck J.R. Afferent arteriolar vasodilation to the sulfonimide analog of 11,12-epoxyeicosatrienoic acid involves protein kinase A. Hypertension 33 (1999) 408-413
28. Cowart L.A., Wei S., Hsu M.H., et al. The CYP4A isoforms hydroxylate epoxyeicosatrienoic acids to form high affinity peroxisome proliferator-activated receptor ligands. J Biol Chem 277 (2002) 35105-35112
29. Liu Y., Zhang Y., Schmelzer K., et al. The antiinflammatory effect of laminar flow: the role of PPARγ, epoxyeicosatrienoic acids, and soluble epoxide hydrolase. Proc Natl Acad Sci USA 102 (2005) 16747-16752
30. Widstrom R.L., Norris A.W., and Spector A.A. Binding of cytochrome P450 monooxygenase and lipoxygenase pathway products by heart fatty acid-binding protein. Biochemistry 40 (2001) 1070-1076
31. Wolfrum C., Borrmann C.M., Borchers T., and Spener F. Fatty acids and hypolipidemic drugs regulate peroxisome proliferator-activated receptors alpha- and gamma-mediated gene expression via liver fatty acid binding protein: A signaling path to the nucleus. Proc Natl Acad Sci USA 98 (2001) 2323-2328
32. Hoebel B.G., and Graier W.F. 11,12-Epoxyeicosatrienoic acid stimulates tyrosine kinase activity in porcine aortic endothelial cells. Eur J Pharmacol 346 (1998) 115-117
33. Fleming I., Fisslthaler B., Michaelis U.R., et al. The coronary endothelium-derived hyperpolarizing factor (EDHF) stimulates multiple signalling pathways and proliferation in vascular cells. Pflugers Arch 442 (2001) 511-518
34. Potente M., Michaelis U.R., Fisslthaler B., Busse R., and Fleming I. Cytochrome P450 2C9-induced endothelial cell proliferation involves induction of mitogen-activated protein (MAP) kinase phosphatase-1, inhibition of the c-Jun N-terminal kinase, and up-regulation of cyclin D1. J Biol Chem 277 (2002) 15671-15676
35. Chen J.K., Wang D.-W., Falck J.R., Capdevila J., and Harris R.C. Transfection of an active cytochrome P450 arachidonic acid epoxygenase indicates that 14,15-epoxyeicosatrienoic acid functions as an intracellular messenger in response to epidermal growth factor. J Biol Chem 274 (1999) 4764-4769
36. Chen J.K., Capdevila J., and Harris R.C. Heparin-binding EGF-like growth factor mediates the biological effects of P450 arachidonate epoxygenase metabolites in epithelial cells. Proc Natl Acad Sci USA 99 (2002) 6029-6034
37. Michaelis U.R., Fisslthaler B., Medhora M., et al. Cytochrome P450 2C9-derived epoxyeicosatrienoic acids induce angiogenesis via cross-talk with the epidermal growth factor receptor (EGFR). FASEB J 17 (2003) 770-772
38. Fleming I., Michaelis U.R., Bredenkotter D., et al. Endothelium-derived hyperpolarizing factor synthase (cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries. Circ Res 88 (2001) 44-51
39. Fichtlscherer S., Dimmeler S., Breuer S., et al. Inhibition of cytochrome P450 2C9 improves endothelium-dependent, nitric oxide-mediated vasodilatation in patients with coronary artery disease. Circulation 109 (2004) 178-183
40. Granville D.J., Tashakkor B., Takeuchi C., et al. Reduction of ischemia and reperfusion-induced myocardial damage by cytochrome P450 inhibitors. Proc Natl Acad Sci USA 101 (2004) 1321-1326
41. Chen J.K., Falck J.R., Reddy K.M., Capdevila J., and Harris R.C. Epoxyeicosatrienoic acids and their sulfonimide derivatives stimulate tyrosine phosphorylation and induce mitogenesis in renal epithelial cells. J Biol Chem 273 (1998) 29254-29261
42. Pozzi A., Macias-Perez I., Abair T., et al. Charaterization of 5,6-and 8,9-epoxyeicosatrienoic acids (5,6- and 8,9-EET) as potent in vivo angiogenic lipids. J Biol Chem 280 (2005) 27138-27146
43. Wang Y., Wei X., Xiao X., et al. Arachidonic acid epoxygenase metabolites stimulate endothelial cell growth and angiogenesis via mitogen-activated protein kinase and phosphatidylinositol 3-kinase/Akt signaling pathways. J Pharmacol Exp Ther 314 (2005) 522-532
44. Potente M., Fisslthaler B., Busse R., and Fleming I. 11,12-epoxyeicosatrienoic acid-induced inhibition of FOXO factors promotes endothelial proliferation by down-regulating p27Kip1. J Biol Chem 278 (2003) 29619-29625
45. Park H.S., Kim M.S., Huh S.H., et al. Akt (protein kinase B) negatively regulates SEK1 by means of protein phosphorylation. J Biol Chem 277 (2002) 2573-2578
46. + channels inhibits proliferation of human endothelial cells induced by basic fibroblast growth factor. J Vasc Res 35 (1998) 363-371
47. + channels in human endothelial cells in culture. Int J Biochem Cell Biol 33 (2001) 337-346
48. +channels contributes to ROS-dependent proliferation of cultured human endothelial cells. J Mol Cell Cardiol 36 (2004) 675-682
49. Sun J., Sui X.X., Bradbury A., et al. Inhibition of vascular smooth muscle cell migration by cytochrome P450 epoxygenase-derived eicosanoids. Circ Res 90 (2002) 1020-1027
50. 2 production in vascular smooth muscle cells. Am J Physiol 275 (1998) H2113-H2121
51. Munzenmaier D.H., and Harder D.R. Cerebral microvascular endothelial cell tube formation: role of astrocytic epoxyeicosatrienoic acid release. Am J Physiol Heart Circ Physiol 278 (2000) H1163-H1167
52. Zhang C., and Harder D.R. Cerebral capillary endothelial cell mitogenesis and morphogenesis induced by astrocytic epoxyeicosatrienoic acid. Stroke 33 (2002) 2957-2964
53. Medhora M., Daniels J., Mundey K., et al. Epoxygenase-driven angiogenesis in human lung microvascular endothelial cells. Am J Physiol Heart Circ Physiol 284 (2003) H215-H224
54. Heissig B., Hattori K., Friedrich M., Rafii S., and Werb Z. Angiogenesis: vascular remodeling of the extracellular matrix involves metalloproteinases. Curr Opin Hematol 10 (2003) 136-141
55. Schlondorff J., and Blobel C.P. Metalloprotease-disintegrins: modular proteins capable of promoting cell-cell interactions and triggering signals by protein-ectodomain shedding. J Cell Sci 112 (1999) 3603-3617
56. Horwitz A.R., and Parsons J.T. Cell migration-movin' on. Science 286 (1999) 1102-1103
57. Michaelis U.R., Falck J.R., Schmidt R., Busse R., and Fleming I. Cytochrome P4502C9-derived epoxyeicosatrienoic acids induce the expression of cyclooxygenase-2 in endothelial cells. Arterioscler Thromb Vasc Biol 25 (2005) 321-326
58. Ito W.D., Arras M., Winkler B., et al. Monocyte chemotactic protein-1 increases collateral and peripheral conductance after femoral artery occlusion. Circ Res 80 (1997) 829-837
59. Node K., Huo Y., Ruan X., et al. Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science 285 (1999) 1276-1279
60. i subunits. Arterioscler Thromb Vasc Biol 22 (2002) 1610-1616
61. Rivilis I., Milkiewicz M., Boyd P., et al. Differential involvement of MMP-2 and VEGF during muscle stretch- versus shear stress-induced angiogenesis. Am J Physiol Heart Circ Physiol 283 (2002) H1430-H1438
62. Yokose T., Doy M., Taniguchi T., et al. Immunohistochemical study of cytochrome P450 2C and 3A in human non- neoplastic and neoplastic tissues. Virchows Arch 434 (1999) 401-411
63. Jiang J.G., Chen C.L., Card J.W., et al. Cytochrome P450 2J2 promotes the neoplastic phenotype of carcinoma cells and is up-regulated in human tumors. Cancer Res 65 (2005) 4707-4715
64. Chun Y.J., and Kim S. Discovery of cytochrome P450 1B1 inhibitors as new promising anti-cancer agents. Med Res Rev 23 (2003) 657-668
65. Stearns V., Johnson M.D., Rae J.M., et al. Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine. J Natl Cancer Inst 95 (2003) 1758-1764
66. Coller J.K. Oxidative metabolism of tamoxifen to Z-4-hydroxy-tamoxifen by cytochrome P450 isoforms: an appraisal of in vitro studies. Clin Exp Pharmacol Physiol 30 (2003) 845-848