Vasorelaxation to N-oleoylethanolamine in rat isolated arteries: Mechanisms of action and modulation via cyclooxygenase activity

British Journal of Pharmacology

Volumn 160, Issue 3, 2010, Pages 701-711

  Wheal, A J ^a   Alexander, S P H ^a   Randall, M D ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Caffeine; Cannabinoid; Cyclooxygenase; Endothelium; Mesenteric arterial beds; N Oleoylethanolamine; Sensory nerves

Indexed keywords

1 (2,4 DICHLOROPHENYL) 5 (4 IODOPHENYL) 4 METHYL N (1 PIPERIDYL) 1H PYRAZOLE 3 CARBOXAMIDE; CAFFEINE; CALCIUM; CAPSAICIN; CHLORIDE CHANNEL; INDOMETACIN; METHOXAMINE; N OLEOYLETHANOLAMINE; POTASSIUM; POTASSIUM CHANNEL; PROSTAGLANDIN SYNTHASE; AMIDE; ANANDAMIDE; ARACHIDONIC ACID DERIVATIVE; CANNABINOID 1 RECEPTOR; ENDOCANNABINOID; ETHANOLAMINE DERIVATIVE; N-OLEOYLETHANOLAMINE; NITRIC OXIDE; OLEIC ACID; PIPERIDINE DERIVATIVE; POTASSIUM CHANNEL BLOCKING AGENT; PYRAZOLE DERIVATIVE;

ANIMAL TISSUE; ARTERY DILATATION; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENTIATION; DRUG PROTEIN BINDING; ENZYME ACTIVITY; MESENTERIC ARTERY; NONHUMAN; PRIORITY JOURNAL; RAT; SENSORY NERVE; THORACIC AORTA; VASCULAR ENDOTHELIUM; ANIMAL; ANTAGONISTS AND INHIBITORS; DRUG EFFECTS; IN VITRO STUDY; MALE; PHYSIOLOGY; SENSORY NERVE CELL; VASODILATATION; WISTAR RAT;

ANIMALS; AORTA, THORACIC; ARACHIDONIC ACIDS; CAFFEINE; CAPSAICIN; CHLORIDE CHANNELS; ENDOCANNABINOIDS; ENDOTHELIUM, VASCULAR; ETHANOLAMINES; IN VITRO TECHNIQUES; INDOMETHACIN; MALE; MESENTERIC ARTERIES; NITRIC OXIDE; OLEIC ACIDS; PIPERIDINES; POLYUNSATURATED ALKAMIDES; POTASSIUM CHANNEL BLOCKERS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PYRAZOLES; RATS; RATS, WISTAR; RECEPTOR, CANNABINOID, CB1; SENSORY RECEPTOR CELLS; VASODILATION;

EID: 77952645922     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2010.00770.x     Document Type: Article

References (55)

1. Ahern GP (2003). Activation of TRPV1 by the satiety factor oleoylethanolamide. J Biol Chem 278 : 30429 30434.
2. Ahluwalia J, Urban L, Capogna M, Bevan S, Nagy I (2000). Cannabinoid 1 receptors are expressed in nociceptive primary sensory neurons. Neuroscience 100 : 685 688.
3. Alexander SPH, Kendall DA (2007). The complications of promiscuity: endocannabinoid action and metabolism. Br J Pharmacol 152 : 602 623.
4. Alexander SPH, Mathie A, Peters JA (2009). Guide to Receptors and Channels (GRAC), 4th edn. Br J Pharmacol 158 : S1 S254.
5. Almasi R, Szoke E, Bolcskei K, Varga A, Riedl Z, Sandor Z et al. (2008). Actions of 3-methyl-N-oleoyldopamine, 4-methyl-N-oleoyldopamine and N-oleoylethanolamide on the rat TRPV1 receptor in vitro and in vivo. Life Sci 82 : 644 651.
6. Artmann A, Petersen G, Hellgren LI, Boberg J, Skonberg C, Nellemann C et al. (2008). Influence of dietary fatty acids on endocannabinoid and N-acylethanolamine levels in rat brain, liver and small intestine. Biochim Biophys Acta 1781 : 200 212.
7. Busse R, Edwards G, Feletou M, Fleming I, Vanhoutte PM, Weston AH (2002). EDHF: bringing the concepts together. Trends Pharmacol Sci 23 : 374 380.
8. Campolongo P, Roozendaal B, Trezza V, Cuomo V, Astarita G, Fu J et al. (2009). Fat-induced satiety factor oleoylethanolamide enhances memory consolidation. Proc Natl Acad Sci U S A 106 : 8027 8031.
9. Chow SC, Jondal M (1990). Polyunsaturated free fatty acids stimulate an increase in cytosolic Ca2+ by mobilizing the inositol 1,4,5-trisphosphate- sensitive Ca2+ pool in T cells through a mechanism independent of phosphoinositide turnover. J Biol Chem 265 : 902 907.
10. Coleman RA, Humphrey PP, Kennedy I, Levy GP, Lumley P (1981). Comparison of the actions of U-46619, a prostaglandin H2-analogue, with those of prostaglandin H2 and thromboxane A2 on some isolated smooth muscle preparations. Br J Pharmacol 73 : 773 778.
11. Criddle DN, de Moura RS, Greenwood IA, Large WA (1997). Inhibitory action of niflumic acid on noradrenaline- and 5-hydroxytryptamine-induced pressor responses in the isolated mesenteric vascular bed of the rat. Br J Pharmacol 120 : 813 818.
12. Drukarch B, Kits KS, Leysen JE, Schepens E, Stoof JC (1989). Restricted usefulness of tetraethylammonium and 4-aminopyridine for the characterization of receptor-operated K+-channels. Br J Pharmacol 98 : 113 118.
13. Fowler CJ (2007a). The contribution of cyclooxygenase-2 to endocannabinoid metabolism and action. Br J Pharmacol 152 : 594 601.
14. Fowler CJ (2007b). The pharmacology of the cannabinoid system - a question of efficacy and selectivity. Mol Neurobiol 36 : 15 25.
15. Fu J, Gaetani S, Oveisi F, Lo Verme J, Serrano A, Rodriguez De Fonseca F et al. (2003). Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-alpha. Nature 425 : 90 93.
16. Gamberucci A, Fulceri R, Benedetti A (1997). Inhibition of store-dependent capacitative Ca2+ influx by unsaturated fatty acids. Cell Calcium 21 : 375 385.
17. Giuffrida A, Rodriguez de Fonseca F, Nava F, Loubet-Lescoulie P, Piomelli D (2000). Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404. Eur J Pharmacol 408 : 161 168.
18. Guzman M, Lo Verme J, Fu J, Oveisi F, Blazquez C, Piomelli D (2004). Oleoylethanolamide stimulates lipolysis by activating the nuclear receptor peroxisome proliferator-activated receptor alpha (PPAR-alpha). J Biol Chem 279 : 27849 27854.
19. Hansen HH, Hansen SH, Schousboe A, Hansen HS (2000). Determination of the phospholipid precursor of anandamide and other N-acylethanolamine phospholipids before and after sodium azide-induced toxicity in cultured neocortical neurons. J Neurochem 75 : 861 871.
20. Harris D, McCulloch AI, Kendall DA, Randall MD (2002). Characterization of vasorelaxant responses to anandamide in the rat mesenteric arterial bed. J Physiol 539 : 893 902.
21. Ho WS, Barrett DA, Randall MD (2008). 'Entourage' effects of N-palmitoylethanolamide and N-oleoylethanolamide on vasorelaxation to anandamide occur through TRPV1 receptors. Br J Pharmacol 155 : 837 846.
22. Ho WS, Randall MD (2007). Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol. Br J Pharmacol 150 : 641 651.
23. Johnson JL, Wimsatt J, Buckel SD, Dyer RD, Maddipati KR (1995). Purification and characterization of prostaglandin H synthase-2 from sheep placental cotyledons. Arch Biochem Biophys 324 : 26 34.
24. Kozlowska H, Baranowska M, Schlicker E, Kozlowski M, Laudanski J, Malinowska B (2008). Virodhamine relaxes the human pulmonary artery through the endothelial cannabinoid receptor and indirectly through a COX product. Br J Pharmacol 155 : 1034 1042.
25. Lambert DM, DiPaolo FG, Sonveaux P, Kanyonyo M, Govaerts SJ, Hermans E et al. (1999). Analogues and homologues of N-palmitoylethanolamide, a putative endogenous CB(2) cannabinoid, as potential ligands for the cannabinoid receptors. Biochim Biophys Acta 1440 : 266 274.
26. Lan R, Liu Q, Fan P, Lin S, Fernando SR, McCallion D et al. (1999). Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J Med Chem 42 : 769 776.
27. Lo Verme J, Gaetani S, Fu J, Oveisi F, Burton K, Piomelli D (2005). Regulation of food intake by oleoylethanolamide. Cell Mol Life Sci 62 : 708 716.
28. McCulloch AI, Bottrill FE, Randall MD, Hiley CR (1997). Characterization and modulation of EDHF-mediated relaxations in the rat isolated superior mesenteric arterial bed. Br J Pharmacol 120 : 1431 1438.
29. Movahed P, Jonsson BA, Birnir B, Wingstrand JA, Jorgensen TD, Ermund A et al. (2005). Endogenous unsaturated C18 N-acylethanolamines are vanilloid receptor (TRPV1) agonists. J Biol Chem 280 : 38496 38504.
30. Mulvany MJ, Halpern W (1977). Contractile properties of small resistance vessels in spontaneously hypertensive and normotensive rats. Circ Res 41, 19 26.
31. O'Sullivan SE (2007). Cannabinoids go nuclear: evidence for activation of peroxisome proliferator-activated receptors. Br J Pharmacol 152 : 576 582.
32. O'Sullivan SE, Kendall DA, Randall MD (2004). Heterogeneity in the mechanisms of vasorelaxation to anandamide in resistance and conduit rat mesenteric arteries. Br J Pharmacol 142 : 435 442.
33. O'Sullivan SE, Kendall DA, Randall MD (2005). Vascular effects of delta 9-tetrahydrocannabinol (THC), anandamide and N-arachidonoyldopamine (NADA) in the rat isolated aorta. Eur J Pharmacol 507 : 211 221.
34. Okamoto Y, Morishita J, Tsuboi K, Tonai T, Ueda N (2004). Molecular characterization of a phospholipase D generating anandamide and its congeners. J Biol Chem 279 : 5298 5305.
35. Overton HA, Babbs AJ, Doel SM, Fyfe MC, Gardner LS, Griffin G et al. (2006). Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents. Cell Metab 3 : 167 175.
36. Randall MD, Kendall DA, O'Sullivan SE (2004). The complexities of the cardiovascular actions of cannabinoids. Br J Pharmacol 142 : 20 26.
37. Richardson D, Ortori CA, Chapman V, Kendall DA, Barrett DA (2007). Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry. Anal Biochem 360 : 216 226.
38. Ryberg E, Larsson N, Sjogren S, Hjorth S, Hermansson NO, Leonova J et al. (2007). The orphan receptor GPR55 is a novel cannabinoid receptor. Br J Pharmacol 152 : 1092 1101.
39. Schwartz GJ, Fu J, Astarita G, Li X, Gaetani S, Campolongo P et al. (2008). The lipid messenger OEA links dietary fat intake to satiety. Cell Metab 8 : 281 288.
40. Scornik FS, Toro L (1992). U46619, a thromboxane A2 agonist, inhibits KCa channel activity from pig coronary artery. Am J Physiol 262 : C708 C713.
41. Sudhahar V, Shaw S, Imig JD (2009). Mechanisms involved in oleamide-induced vasorelaxation in rat mesenteric resistance arteries. Eur J Pharmacol 607 : 143 150.
42. Sun Y, Alexander SP, Garle MJ, Gibson CL, Hewitt K, Murphy SP et al. (2007). Cannabinoid activation of PPAR alpha; a novel neuroprotective mechanism. Br J Pharmacol 152 : 734 743.
43. Szallasi A, Blumberg PM (1999). Vanilloid (Capsaicin) receptors and mechanisms. Pharmacol Rev 51 : 159 212.
44. Tep-Areenan P, Kendall DA, Randall MD (2003a). Mechanisms of vasorelaxation to 17beta-oestradiol in rat arteries. Eur J Pharmacol 476 : 139 149.
45. Tep-Areenan P, Kendall DA, Randall MD (2003b). Mechanisms of vasorelaxation to testosterone in the rat aorta. Eur J Pharmacol 465 : 125 132.
46. Tsuboi K, Sun YX, Okamoto Y, Araki N, Tonai T, Ueda N (2005). Molecular characterization of N-acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase. J Biol Chem 280 : 11082 11092.
47. Ueda N, Yamanaka K, Yamamoto S (2001). Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance. J Biol Chem 276 : 35552 35557.
48. Venance L, Sagan S, Giaume C (1997). R)-methanandamide inhibits receptor-induced calcium responses by depleting internal calcium stores in cultured astrocytes. Pflugers Arch 434 : 147 149.
49. Wheal AJ, Alexander SPH, Randall MD (2009). Effect of contractile agents on vasorelaxation to oleoylethanolamide in isolated aortic rings from spontaneously hypertensive rats. Abstract presented at the British Pharmacological Society's summer meeting: http://www.pA2online.org/abstracts/ Vol7Issue2abst022P.pdf.
50. White R, Hiley CR (1998). The actions of some cannabinoid receptor ligands in the rat isolated mesenteric artery. Br J Pharmacol 125 : 533 541. (Pubitemid 28451492)
51. White R, Ho WS, Bottrill FE, Ford WR, Hiley CR (2001). Mechanisms of anandamide-induced vasorelaxation in rat isolated coronary arteries. Br J Pharmacol 134 : 921 929.
52. Yamagishi T, Yanagisawa T, Taira N (1992). Ca2+ influx induced by the agonist U46619 is inhibited by hyperpolarization induced by the K+ channel opener cromakalim in canine coronary artery. Jpn J Pharmacol 59 : 291 299.
53. Yuan C, Sidhu RS, Kuklev DV, Kado Y, Wada M, Song I et al. (2009). Cyclooxygenase Allosterism, Fatty Acid-mediated Cross-talk between Monomers of Cyclooxygenase Homodimers. J Biol Chem 284 : 10046 10055.
54. Zygmunt PM, Hogestatt ED, Waldeck K, Edwards G, Kirkup AJ, Weston AH (1997). Studies on the effects of anandamide in rat hepatic artery. Br J Pharmacol 122 : 1679 1686.
55. Zygmunt PM, Petersson J, Andersson DA, Chuang H, Sorgard M, Di Marzo V et al. (1999). Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 400 : 452 457.