Identification of 13-hydroxy-14,15-epoxyeicosatrienoic acid as an acid-stable endothelium-derived hyperpolarizing factor in rabbit arteries

Journal of Biological Chemistry

Volumn 284, Issue 45, 2009, Pages 31280-31290

  Chawengsub, Yuttana ^a   Gauthier, Kathryn M ^a   Nithipatikom, Kasem ^a   Hammock, Bruce D ^b   Falck, John R ^c   Narsimhaswamy, Dubasi ^c   Campbell, William B ^a,d  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^d NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

15-LIPOXYGENASE; ACIDIC HYDROLYSIS; ANGIOTENSIN II; ARACHIDONIC ACIDS; CHANNEL ACTIVATION; CYTOCHROME P450; DIASTEREOMERS; EICOSANOIDS; EPOXYEICOSATRIENOIC ACIDS; ERYTHRO; HYPERPOLARIZATION; IN-CELL; MASS SPECTROMETRIC ANALYSIS; MESENTERIC ARTERIES; POLAR METABOLITE; SMOOTH MUSCLE CELLS; VASCULAR ACTIVITY;

BIOMOLECULES; BLOOD VESSELS; HYDROLYSIS; ISOMERS; MASS SPECTROMETERS; MASS SPECTROMETRY; METABOLISM; METABOLITES; MUSCLE; SELF ASSEMBLY;

ACIDS;

13 HYDROXY 14,15 EPOXYEICOSATRIENOIC ACID; APAMIN; ARACHIDONIC ACID; CYTOCHROME P450 2J2; EPOXYICOSATRIENOIC ACID; LIPOXYGENASE; SMALL CONDUCTANCE CALCIUM ACTIVATED POTASSIUM CHANNEL; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ENZYME ACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; HYPERPOLARIZATION; MASS SPECTROMETRY; MESENTERIC ARTERY; NONHUMAN; PRIORITY JOURNAL; RABBIT; VASCULAR ENDOTHELIUM;

8,11,14-EICOSATRIENOIC ACID; ACIDS; ANIMALS; ARACHIDONIC ACID; ARTERIES; ENDOTHELIUM, VASCULAR; RABBITS; VASODILATOR AGENTS;

ORYCTOLAGUS CUNICULUS;

EID: 71449107550     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M109.025627     Document Type: Article

References (61)

1. Moncada, S., and Vane, J. R. (1978) Pharmacol. Rev. 30, 293-331
2. Moncada, S., Herman, A. G., and Vanhoutte, P. (1987) Trends Pharmacol. Sci. 8, 365-368
3. Dembinska-Kiec, A., Gryglewska, T., Zmuda, A., and Gryglewski, R. J. (1977) Prostaglandins 14, 1025-1034
4. Russo, G., Leopold, J. A., and Loscalzo, J. (2002) Vascul. Pharmacol. 38, 259-269
5. Voetsch, B., Jin, R. C., and Loscalzo, J. (2004) Histochem. Cell Biol. 122, 353-367
6. Félétou, M., and Vanhoutte, P. M. (2007) Ann. Med. 39, 495-516
7. Bolton, T. B., and Clapp, L. H. (1986) Br. J. Pharmacol. 87, 713-723
8. Feletou, M., and Vanhoutte, P. M. (1988) Br. J. Pharmacol. 93, 515-524
9. Taylor, S. G., Southerton, J. S., Weston, A. H., and Baker, J. R. J. (1988) Br. J. Pharmacol. 94, 853-863
10. Chen, G., Suzuki, H., and Weston, A. H. (1988) Br. J. Pharmacol. 95, 1165-1174
11. Campbell, W. B., Spitzbarth, N., Gauthier, K. M., and Pfister, S. L. (2003) Am. J. Physiol. Heart Circ. Physiol. 285, H2648-H2656
12. Tang, X., Holmes, B. B., Nithipatikom, K., Hillard, C. J., Kuhn, H., and Campbell, W. B. (2006) Arterioscler. Thromb. Vasc. Biol. 26, 78-84
13. Pfister, S. L., Spitzbarth, N., Gauthier, K. M., and Campbell, W. B. (2001) Identification of 11,12,15-Trihydroxyeicosatrienoic Acid as the Mediator of Acetylcholine- and Arachidonic Acid-induced Relaxations in the Rabbit Aorta, Taylor and Francis, London
14. Pfister, S. L., Spitzbarth, N., Nithipatikom, K., Edgemond, W. S., Falck, J. R., and Campbell, W. B. (1998) J. Biol. Chem. 273, 30879-30887
15. Chawengsub, Y., Aggarwal, N. T., Nithipatikom, K., Gauthier, K. M., Anjaiah, S., Hammock, B. D., Falck, J. R., and Campbell, W. B. (2008) Am. J. Physiol. Heart Circ. Physiol. 294, H1348-H1356
16. Gauthier, K. M., Spitzbarth, N., Edwards, E. M., and Campbell, W. B. (2004) Hypertension 43, 413-419
17. Gauthier, K. M., Chawengsub, Y., Goldman, D. H., Conrow, R. E., Anjaiah, S., Falck, J. R., and Campbell, W. B. (2008) Am. J. Physiol. Heart Circ. Physiol. 294, H1467-H1472
18. Nie, D. (2007) Front Biosci. 12, 1574-1585
19. Wittwer, J., and Hersberger, M. (2007) Prostaglandins Leukot Essent Fatty Acids 77, 67-77
20. Natarajan, R., and Nadler, J. L. (2003) Front Biosci. 8, s783-795
21. Corey, E. J., Guo Su, W., and Mehrotra, M. M. (1984) Tetrahedron Lett. 25, 5123-5126
22. Corey, E. J., and Mehrotra, M. M. (1983) Tetrahedron Lett. 24, 4921-4922
23. Pfister, S. L., Spitzbarth, N., Edgemond, W., and Campbell, W. B. (1996) Am. J. Physiol. 270, H1021-H1030
24. Tang, X., Edwards, E. M., Holmes, B. B., Falck, J. R., and Campbell, W. B. (2006) Am. J. Physiol. Heart Circ. Physiol. 290, H37-H45
25. Powell, W. S. (1980) Prostaglandins 20, 947-957
26. Pfister, S. L., Schmitz, J. M., Willerson, J. T., and Campbell, W. B. (1988) Prostaglandins 36, 515-532
27. Cui, L., Isbell, M. A., Chawengsub, Y., Falck, J. R., Campbell, W. B., and Nithipatikom, K. (2008) J. Am. Soc. Mass Spectrom. 19, 569-585
28. Zhang, D. X., Gauthier, K. M., and Campbell, W. B. (2004) Endocrinology 145, 1571-1578
29. Herlihy, J. T., and Murphy, R. A. (1973) Circ. Res. 33, 275-283
30. Gebremedhin, D., Ma, Y. H., Falck, J. R., Roman, R. J., VanRollins, M., and Harder, D. R. (1992) Am. J. Physiol. 263, H519-H525
31. Pfister, S. L., Kotulock, D. A., and Campbell, W. B. (1997) Hypertension 29, 303-309
32. Pfister, S. L., Spitzbarth, N., Zeldin, D. C., Lafite, P., Mansuy, D., and Campbell, W. B. (2003) Arch. Biochem. Biophys. 420, 142-152
33. Weiss, R. H., Arnold, J. L., and Estabrook, R. W. (1987) Arch. Biochem. Biophys. 252, 334-338
34. Aggarwal, N. T., Pfister, S. L., and Campbell, W. B. (2008) Arterioscler. Thromb. Vasc. Biol. 28, 2209-2215
35. Aggarwal, N. T., Chawengsub, Y., Gauthier, K. M., Viita, H., Yla-Herttuala, S., and Campbell, W. B. (2008) Hypertension 51, 246-251
36. Vanhoutte, P. M. (2004) Pharmacol. Res. 49, 503-508
37. Singer, H. A., and Peach, M. J. (1983) J. Pharmacol. Exp. Ther. 226, 790-795
38. Pfister, S. L., and Campbell, W. B. (1992) Hypertension 20, 682-689
39. Zhang, D. X., Gauthier, K. M., Chawengsub, Y., Holmes, B. B., and Campbell, W. B. (2005) Am. J. Physiol. Heart Circ. Physiol. 288, H302-H309
40. Narumiya, S., Salmon, J. A., Cottee, F. H., Weatherley, B. C., and Flower, R. J. (1981) J. Biol. Chem. 256, 9583-9592
41. Yeh, H. C., Tsai, A. L., and Wang, L. H. (2007) Arch. Biochem. Biophys. 461, 159-168
42. Hamberg, M. (1999) Lipids 34, 1131-1142
43. Hamberg, M., and Hamberg, G. (1990) Arch. Biochem. Biophys. 283, 409-416
44. Reynaud, D., Clark, D., Qiao, N., Rand, M. L., and Pace-Asciak, C. R. (2003) Thromb. Res. 112, 245-248
45. Roy, U., Joshua, R., Stark, R. L., and Balazy, M. (2005) Biochem. J. 390, 719-727
46. Gill, S. S., and Hammock, B. D. (1979) Biochem. Biophys. Res. Commun. 89, 965-971
47. Jiang, H., Zhu, A. G., Mamczur, M., Morisseau, C., Hammock, B. D., Falck, J. R., and McGiff, J. C. (2008) J. Pharmacol. Exp. Ther. 326, 330-337
48. Dietze, E. C., Kuwano, E., Casas, J., and Hammock, B. D. (1991) Biochem. Pharmacol. 42, 1163-1175
49. Mrsny, R. J., Gewirtz, A. T., Siccardi, D., Savidge, T., Hurley, B. P., Madara, J. L., and McCormick, B. A. (2004) Proc. Natl. Acad. Sci. U.S.A. 101, 7421-7426
50. Pace-Asciak, C. R., Reynaud, D., Demin, P., and Nigam, S. (1999) Adv. Exp. Med. Biol. 447, 123-132
51. Nigam, S., Patabhiraman, S., Ciccoli, R., Ishdorj, G., Schwarz, K., Petrucev, B., Kühn, H., and Haeggström, J. Z. (2004) J. Biol. Chem. 279, 29023-29030
52. Chang, M. S., Boeglin, W. E., Guengerich, F. P., and Brash, A. R. (1996) Biochemistry 35, 464-471
53. Brash, A. R., Chang, M. S., Funk, C. D., and Song, W. (1994) Ann. N.Y. Acad. Sci. 744, 25-30
54. McCallum, G. P., Weedon, A. C., Krug, P., and Bend, J. R. (1996) J. Pharmacol. Exp. Ther. 278, 1188-1194
55. Förstermann, U., Hertting, G., and Neufang, B. (1984) Br. J. Pharmacol. 81, 623-630
56. Félétou, M., and Vanhoutte, P. M. (2004) Pharmacol. Res. 49, 565-580
57. Panza, J. A., Casino, P. R., Kilcoyne, C. M., and Quyyumi, A. A. (1993) Circulation 87, 1468-1474
58. Fisslthaler, B., Popp, R., Michaelis, U. R., Kiss, L., Fleming, I., and Busse, R. (2001) Hypertension 38, 1427-1432
59. Taddei, S., Versari, D., Cipriano, A., Ghiadoni, L., Galetta, F., Franzoni, F., Magagna, A., Virdis, A., and Salvetti, A. (2006) J. Am. Coll. Cardiol. 48, 508-515
60. Brandes, R. P., Behra, A., Lebherz, C., Böger, R. H., Bode-Böger, S. M., Phivthong-Ngam, L., and Mügge, A. (1997) Atherosclerosis 135, 49-55
61. Honda, H., Moroe, H., Fujii, H., Arai, K., Notoya, Y., and Kogo, H. (2001) Jpn. J. Pharmacol. 85, 203-206