Cannabinoid receptor antagonists and fatty acids alter endocannabinoid system gene expression and COX activity

Journal of Nutritional Biochemistry

Volumn 25, Issue 8, 2014, Pages 815-823

  Kim, Jeffrey ^a   Watkins, Bruce A ^a,b  

^a Lipid Chemistry and Molecular Biology Laboratory   (United States)

^b UNIVERSITY OF CONNECTICUT HEALTH CENTER   (United States)

Author keywords

C2C12 myoblasts; Cannabinoid receptors; Cyclooxygenase; Endocannabinoids; Polyunsaturated fatty acids

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 6 IODO 3 (4 METHOXYBENZOYL) 2 METHYL 1 (2 MORPHOLINOETHYL)INDOLE; ANANDAMIDE; ARACHIDONIC ACID; BOVINE SERUM ALBUMIN; CANNABINOID 1 RECEPTOR; CANNABINOID 1 RECEPTOR ANTAGONIST; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR ANTAGONIST; CYCLOOXYGENASE 1; DIACYLGLYCEROL LIPASE ALPHA; DIACYLGLYCEROL LIPASE BETA; DOCOSAHEXAENOIC ACID; ENDOCANNABINOID; FATTY ACID; GLYCOSYLPHOSPHATIDYLINOSITOL PHOSPHOLIPASE D; ICOSAPENTAENOIC ACID; INTERLEUKIN 6; LIPOPROTEIN LIPASE; MESSENGER RNA; NESS 0327; POLYUNSATURATED FATTY ACID; PROSTAGLANDIN; PROSTAGLANDIN SYNTHASE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; 2-ARACHIDONYLGLYCEROL; ACYLGLYCEROL; ARACHIDONIC ACID DERIVATIVE; INDOLE DERIVATIVE; IODOPRAVADOLINE; N-PIPERIDINYL-(8-CHLORO-1-(2,4-DICHLOROPHENYL)-1,4,5,6-TETRAHYDROBENZO(6,7)CYCLOHEPTA(1,2-C)PYRAZOLE-3-CARBOXAMIDE); PIPERIDINE DERIVATIVE; PYRAZOLE DERIVATIVE; UNSATURATED FATTY ACID;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME SUBSTRATE COMPLEX; GENE EXPRESSION; HUMAN; HUMAN CELL; INVERSE AGONISM; MYOBLAST; POLYMERASE CHAIN REACTION; QUANTITATIVE ANALYSIS; RECEPTOR DOWN REGULATION; RECEPTOR UPREGULATION; ANIMAL; CYTOLOGY; DRUG EFFECTS; GENE EXPRESSION REGULATION; GENETICS; INFLAMMATION; METABOLISM; MOUSE;

BOVINAE;

ANIMALS; ARACHIDONIC ACID; ARACHIDONIC ACIDS; CANNABINOID RECEPTOR ANTAGONISTS; ENDOCANNABINOIDS; FATTY ACIDS, UNSATURATED; GENE EXPRESSION REGULATION; GLYCERIDES; INDOLES; INFLAMMATION; INTERLEUKIN-6; LIPOPROTEIN LIPASE; MICE; MYOBLASTS; PIPERIDINES; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PYRAZOLES; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84903752092     PISSN: 09552863     EISSN: 18734847     Source Type: Journal    
DOI: 10.1016/j.jnutbio.2014.03.012     Document Type: Article

References (55)

1. Yu M., Ives D., Ramesha C.S. Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 1997, 272(34):21181-21186.
2. Kozak K.R., Rowlinson S.W., Marnett L.J. Oxygenation of the endocannabinoid, 2-arachidonylglycerol, to glyceryl prostaglandins by cyclooxygenase-2. J Biol Chem 2000, 275(43):33744-33749.
3. Jhaveri M.D., Richardson D., Robinson I., et al. Inhibition of fatty acid amide hydrolase and cyclooxygenase-2 increases levels of endocannabinoid related molecules and produces analgesia via peroxisome proliferator-activated receptor-alpha in a model of inflammatory pain. Neuropharmacology 2008, 55(1):85-93.
4. Wahn H., Wolf J., Kram F., et al. The endocannabinoid arachidonyl ethanolamide (anandamide) increases pulmonary arterial pressure via cyclooxygenase-2 products in isolated rabbit lungs. Am J Physiol Heart Circ Physiol 2005, 289(6):H2491-H2496.
5. Kozak K.R., Crews B.C., Morrow J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J Biol Chem 2002, 277(47):44877-44885.
6. Kozak K.R., Prusakiewicz J.J., Marnett L.J. Oxidative metabolism of endocannabinoids by COX-2. Curr Pharm Des 2004, 10(6):659-667.
7. Sang N., Zhang J., Chen C. PGE2 glycerol ester, a COX-2 oxidative metabolite of 2-arachidonoyl glycerol, modulates inhibitory synaptic transmission in mouse hippocampal neurons. J Physiol 2006, 572(Pt 3):735-745.
8. Zygmunt P.M., Petersson J., Andersson D.A., et al. Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 1999, 400(6743):452-457.
9. Ross R.A. Anandamide and vanilloid TRPV1 receptors. Br J Pharmacol 2003, 140(5):790-801.
10. De Petrocellis L., Di Marzo V. Lipids as regulators of the activity of transient receptor potential type V1 (TRPV1) channels. Life Sci 2005, 77(14):1651-1666.
11. Alger B.E. Endocannabinoid identification in the brain: studies of breakdown lead to breakthrough, and there may be NO hope. Sci STKE 2005, 2005(309):e51.
12. Bisogno T., Ligresti A., Di Marzo V. The endocannabinoid signalling system: biochemical aspects. Pharmacol Biochem Behav 2005, 81(2):224-238.
13. Sugiura T., Kishimoto S., Oka S., et al. Biochemistry, pharmacology and physiology of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. Prog Lipid Res 2006, 45(5):405-446.
14. Zhang J., Chen C. Endocannabinoid 2-arachidonoylglycerol protects neurons by limiting COX-2 elevation. J Biol Chem 2008, 283(33):22601-22611.
15. Hohmann A.G., Suplita R.L. Endocannabinoid mechanisms of pain modulation. AAPS J 2006, 8(4):E693-E708.
16. Jhaveri M.D., Richardson D., Chapman V. Endocannabinoid metabolism and uptake: novel targets for neuropathic and inflammatory pain. Br J Pharmacol 2007, 152(5):624-632.
17. Prieto S., Grau J.M. The geoepidemiology of autoimmune muscle disease. Autoimmun Rev 2010, 9(5):A330-A334.
18. Mammen A.L. Autoimmune myopathies: autoantibodies, phenotypes and pathogenesis. Nat Rev Neurol 2011, 7(6):343-354.
19. Engel WK. The essentiality of histo- and cytochemical studies of skeletal muscle in the investigation of neuromuscular disease. 1962. Neurology 1998; 51(3):655 and 17 pages following.
20. Schaap L.A., Pluijm S.M., Deeg D.J., et al. Inflammatory markers and loss of muscle mass (sarcopenia) and strength. Am J Med 2006, 119(6):526.e9-526.e17.
21. Cannon J.G. Intrinsic and extrinsic factors in muscle aging. Ann N Y Acad Sci 1998, 854:72-77.
22. Roubenoff R., Harris T.B., Abad L.W., et al. Monocyte cytokine production in an elderly population: effect of age and inflammation. J Gerontol A Biol Sci Med Sci 1998, 53(1):M20-M26.
23. Roubenoff R., Parise H., Payette H.A., et al. Cytokines, insulin-like growth factor 1, sarcopenia, and mortality in very old community-dwelling men and women: the Framingham Heart Study. Am J Med 2003, 115(6):429-435.
24. Payette H., Roubenoff R., Jacques P.F., et al. Insulin-like growth factor-1 and interleukin 6 predict sarcopenia in very old community-living men and women: the Framingham Heart Study. J Am Geriatr Soc 2003, 51(9):1237-1243.
25. Paul W.E., Seder R.A. Lymphocyte responses and cytokines. Cell 1994, 76(2):241-251.
26. Bartoccioni E., Michaelis D., Hohlfeld R. Constitutive and cytokine-induced production of interleukin-6 by human myoblasts. Immunol Lett 1994, 42(3):135-138.
27. Sugamura K., Sugiyama S., Nozaki T., et al. Activated endocannabinoid system in coronary artery disease and antiinflammatory effects of cannabinoid 1 receptor blockade on macrophages. Circulation 2009, 119(1):28-36.
28. Gallily R., Breuer A., Mechoulam R. 2-Arachidonylglycerol, an endogenous cannabinoid, inhibits tumor necrosis factor-alpha production in murine macrophages, and in mice. Eur J Pharmacol 2000, 406(1):R5-R7.
29. Schwarz H., Blanco F.J., Lotz M. Anadamide, an endogenous cannabinoid receptor agonist inhibits lymphocyte proliferation and induces apoptosis. J Neuroimmunol 1994, 55(1):107-115.
30. Valk P., Verbakel S., Vankan Y., et al. Anandamide, a natural ligand for the peripheral cannabinoid receptor is a novel synergistic growth factor for hematopoietic cells. Blood 1997, 90(4):1448-1457.
31. Ihenetu K., Molleman A., Parsons M.E., et al. Inhibition of interleukin-8 release in the human colonic epithelial cell line HT-29 by cannabinoids. Eur J Pharmacol 2003, 458(1-2):207-215.
32. Li Y., Seifert M.F., Lim S.Y., et al. Bone mineral content is positively correlated to n-3 fatty acids in the femur of growing rats. Br J Nutr 2010, 104(5):674-685.
33. Cavuoto P., McAinch A.J., Hatzinikolas G., et al. The expression of receptors for endocannabinoids in human and rodent skeletal muscle. Biochem Biophys Res Commun 2007, 364(1):105-110.
34. Wright K., Rooney N., Feeney M., et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology 2005, 129(2):437-453.
35. Brown I., Cascio M.G., Wahle K.W., et al. Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis 2010, 31(9):1584-1591.
36. Sheskin T., Hanus L., Slager J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 1997, 40(5):659-667.
37. Gao Y., Vasilyev D.V., Goncalves M.B., et al. Loss of retrograde endocannabinoid signaling and reduced adult neurogenesis in diacylglycerol lipase knock-out mice. J Neurosci 2010, 30(6):2017-2024.
38. Cravatt B.F., Demarest K., Patricelli M.P., et al. Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase. Proc Natl Acad Sci U S A 2001, 98(16):9371-9376.
39. Lichtman A.H., Leung D., Shelton C.C., et al. Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity. J Pharmacol Exp Ther 2004, 311(2):441-448.
40. Fegley D., Gaetani S., Duranti A., et al. Characterization of the fatty acid amide hydrolase inhibitor cyclohexyl carbamic acid 3'-carbamoyl-biphenyl-3-yl ester (URB597): effects on anandamide and oleoylethanolamide deactivation. J Pharmacol Exp Ther 2005, 313(1):352-358.
41. Jayamanne A., Greenwood R., Mitchell V.A., et al. Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models. Br J Pharmacol 2006, 147(3):281-288.
42. Weber A., Ni J., Ling K.H., et al. Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometry. J Lipid Res 2004, 45(4):757-763.
43. Berger C., Schmid P.C., Schabitz W.R., et al. Massive accumulation of N-acylethanolamines after stroke. Cell signalling in acute cerebral ischemia?. J Neurochem 2004, 88(5):1159-1167.
44. Collaco-Moraes Y., Aspey B., Harrison M., et al. Cyclo-oxygenase-2 messenger RNA induction in focal cerebral ischemia. J Cereb Blood Flow Metab 1996, 16(6):1366-1372.
45. Svensson C.I., Yaksh T.L. The spinal phospholipase-cyclooxygenase-prostanoid cascade in nociceptive processing. Annu Rev Pharmacol Toxicol 2002, 42:553-583.
46. Massa F., Marsicano G., Hermann H., et al. The endogenous cannabinoid system protects against colonic inflammation. J Clin Invest 2004, 113(8):1202-1209.
47. D'Argenio G., Valenti M., Scaglione G., et al. Up-regulation of anandamide levels as an endogenous mechanism and a pharmacological strategy to limit colon inflammation. FASEB J 2006, 20(3):568-570.
48. Kimball E.S., Schneider C.R., Wallace N.H., et al. Agonists of cannabinoid receptor 1 and 2 inhibit experimental colitis induced by oil of mustard and by dextran sulfate sodium. Am J Physiol Gastrointest Liver Physiol 2006, 291(2):G364-G371.
49. O'Neill G.P., Ford-Hutchinson A.W. Expression of mRNA for cyclooxygenase-1 and cyclooxygenase-2 in human tissues. FEBS Lett 1993, 330(2):156-160.
50. Seibert K., Zhang Y., Leahy K., et al. Distribution of COX-1 and COX-2 in normal and inflamed tissues. Adv Exp Med Biol 1997, 400A:167-170.
51. Felder C.C., Briley E.M., Axelrod J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci U S A 1993, 90(16):7656-7660.
52. Howlett A.C. Cannabinoid receptor signaling. Handb Exp Pharmacol 2005, 168:53-79.
53. Vecchio A.J., Malkowski M.G. The structural basis of endocannabinoid oxygenation by Cyclooxygenase-2. J Biol Chem 2011, 286(23):20736-20745.
54. Sordelli M.S., Beltrame J.S., Cella M., et al. Cycooxygenase-2 prostaglandins mediate anandamide-inhibitory action on nitric oxide synthase activity in the receptive rat uterus. Eur J Pharmacol 2012, 685:174-179.
55. Woodard D.F., Carling R.W.C., Cornell C.L., et al. The pharmacology and therapeutic relevance of endocannabinoid derived cyclo-oxygenase (COX)-2 products. Pharmacol Ther 2008, 120(1):71-80.