Substituted adamantyl-urea inhibitors of the soluble epoxide hydrolase dilate mesenteric resistance vessels

Journal of Pharmacology and Experimental Therapeutics

Volumn 318, Issue 3, 2006, Pages 1307-1314

  Olearczyk, Jeffrey J ^a   Field, Mary B ^a   Kim, In Hae ^b   Morisseau, Christophe ^b   Hammock, Bruce D ^b   Imig, John D ^a  

^a MEDICAL COLLEGE OF GEORGIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ADAMANTYL 3 (12 AMINODODECYL)UREA; 1 CYCLOHEXYL 3 DODECYLUREA; 12 (3 ADAMANTAN 1 YLUREIDO)DODECANOIC ACID; 12 (3 CYCLOHEXYLUREIDO)DODECANOIC ACID; 15 HYDROXY 11ALPHA,9ALPHA EPOXYMETHANOPROSTA 5,13 DIENOIC ACID; 4 (3 ADAMANTAN 1 YLUREIDO)BUTANOIC ACID; 6 (3 ADAMANTYLUREIDO)HEXANOIC ACID; 8 (3 ADAMANTYLUREIDO)OCTANOIC ACID; ADAMANTAN 1 YL 3 [5 [2 (2 ETHOXYETHOXY)ETHOXY]PENTYL]UREA; EPOXIDE HYDROLASE; GLIBENCLAMIDE; HYDROLASE INHIBITOR; IBERIOTOXIN; OUABAIN; POTASSIUM CHLORIDE; TETRYLAMMONIUM; THROMBOXANE A2 RECEPTOR STIMULATING AGENT; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BLOOD PRESSURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INHIBITION; HEART PROTECTION; IC 50; MALE; MESENTERY BLOOD VESSEL; NONHUMAN; PRIORITY JOURNAL; RAT; VASCULAR RESISTANCE; VASCULAR SMOOTH MUSCLE; VASCULARIZATION; VASOCONSTRICTION; VASODILATATION;

ADAMANTANE; ANIMALS; ENZYME INHIBITORS; EPOXIDE HYDROLASES; LAURIC ACIDS; MALE; MESENTERIC ARTERIES; NA(+)-K(+)-EXCHANGING ATPASE; PEPTIDES; POTASSIUM CHANNELS; RATS; RATS, SPRAGUE-DAWLEY; TETRAETHYLAMMONIUM COMPOUNDS; VASCULAR RESISTANCE; VASODILATION;

EID: 33747611948     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.106.103556     Document Type: Article

References (26)

1. Campbell WB, Gebremedhin D, Pratt PF, and Harder DR (1996) Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors. Circ Res 78:415-423.
2. Chataigneau T, Feletou M, Duhault J, and Vanhoutte PM (1998) Epoxyeicosatrienoic acids, potassium channel blockers and endothelium-dependent hyperpolarization in the guinea-pig carotid artery. Br J Pharmacol 123:574-580.
3. Enayetallah AE, French RA, Barber M, and Grant DF (2006) Cell-specific subcellular localization of soluble epoxide hydrolase in human tissues. J Histochem Cytochem 54:329-335.
4. Falck JR, Reddy LM, Reddy YK, Bondlela M, Krishna UM, Ji Y, Sun J, and Liao JK (2003) 11,12-epoxyeicosatrienoic acid (11,12-EET): structural determinants for inhibition of TNF-alpha-induced VCAM-1 expression. Bioorg Med Chem Lett 13:4011-4014.
5. Fisslthaler B, Popp R, Kiss L, Potente M, Harder DR, Fleming I, and Busse R (1999) Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature (Lond) 401:493-497.
6. Imig JD, Zhao X, Capdevila JH, Morisseau C, and Hammock BD (2002) Soluble epoxide hydrolase inhibition lowers arterial blood pressure in angiotensin II hypertension. Hypertension 39:690-694.
7. Imig JD, Zhao X, Zharis C, Olearczyk JJ, Pollock DM, Newman JW, Kim I-H, Watanabe T, and Hammock BD (2005) An orally active epoxide hydrolase inhibitor lowers blood pressure and provides renal protection in salt-sensitive hypertension. Hypertension 46:1-7.
8. Kim IH, Morisseau C, Watanabe T, and Hammock BD (2004) Design, synthesis, and biological activity of 1,3-disubstituted ureas as potent inhibitors of the soluble epoxide hydrolase of increased water solubility. J Med Chem 47:2110-2122.
9. Moghaddam MF, Grant DF, Cheek JM, Greene JF, Williamson KC, and Hammock BD (1997) Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase. Nat Med 3:562-566.
10. Morisseau C, Goodrow MH, Newman JW, Wheelock CE, Dowdy DL, and Hammock BD (2002) Structural refinement of inhibitors of urea-based soluble epoxide hydrolases. Biochem Pharmacol 63:1599-1608.
11. Morisseau C and Hammock BD (2005) Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. Annu Rev Pharmacol Toxicol 45:311-333.
12. Newman JW, Morisseau C, and Hammock BD (2005) Epoxide hydrolases: their roles and interactions with lipid metabolism. Prog Lipid Res 44:1-51.
13. Node K, Huo Y, Ruan X, Yang B, Spiecker M, Ley K, Zeldin DC, and Liao JK (1999) Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science (Wash DC) 285:1276-1279.
14. Pratt PF, Li P, Hillard CJ, Kurian J, and Campbell WB (2001) Endotheliumin-dependent, ouabain-sensitive relaxation of bovine coronary arteries by EETs. Am J Physiol 280:H1113-H1121.
15. Schmelzer KR, Kubala L, Newman JW, Kim IH, Eiserich JP, and Hammock BD (2005) Soluble epoxide hydrolase is a therapeutic target for acute inflammation. Proc Natl Acad Sci USA 102:9772-9777.
16. Smith KR, Pinkerton KE, Watanabe T, Pedersen TL, Ma SJ, and Hammock BD (2005) Attenuation of tobacco smoke-induced lung inflammation by treatment with a soluble epoxide hydrolase inhibitor. Proc Natl Acad Sci USA 102:2186-2191.
17. Spector AA, Fang X, Snyder GD, and Weintraub NL (2004) Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function. Prog Lipid Res 43:55-90.
18. Wang P, Meijer J, and Guengerich FP (1982) Purification of human liver cytosolic epoxide hydrolase and comparison to the microsomal enzyme. Biochemistry 21:5769-5776.
19. (+) channels in pituitary GH(3) cells. Biochem Pharmacol 60:251-262.
20. Yang W, Gauthier KM, Reddy LM, Sangras B, Sharma KK, Nithipatikom K, Falck JR, and Campbell WB (2005) Stable 5,6-epoxyeicosatrienoic acid analog relaxes coronary arteries through potassium channel activation. Hypertension 45:681-686.
21. Ye D, Zhou W, and Lee HC (2005) Activation of rat mesenteric arterial KATP channels by 11,12-epoxyeicosatrienoic acid. Am J Physiol 288:H358-H364.
22. Ye D, Zhou W, Lu T, Jagadeesh SG, Falck JR, and Lee HC (2006) Mechanism of rat mesenteric arterial KATP channel activation by 14,15-epoxyeicosatrienoic acid. Am J Physiol 290:H1326-H1336.
23. Yu Z, Davis BB, Morisseau C, Hammock BD, Olson JL, Kroetz DL, and Weiss RH (2004) Vascular localization of soluble epoxide hydrolase in the human kidney. Am J Physiol 286:F720-F726.
24. Yu Z, Xu F, Huse LM, Morisseau C, Draper AJ, Newman JW, Parker C, Graham L, Engler MM, Hammock BD, Zeldin DC, and Kroetz DL (2000) Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ Res 87:992-998.
25. Zeldin DC (2001) Epoxygenase pathways of arachidonic acid metabolism. J Biol Chem 276:36059-36062.
26. Zhao X, Yamamoto T, Newman JW, Kim IH, Watanabe T, Hammock BD, Stewart J, Pollock JS, Pollock DM, and Imig JD (2004) Soluble epoxide hydrolase inhibition protects the kidney from hypertension-induced damage. J Am Soc Nephrol 15:1244-1253.