Effect of nitric oxide donors on membrane tritium accumulation of endocannabinoids and related endogenous lipids

European Journal of Pharmacology

Volumn 621, Issue 1-3, 2009, Pages 10-18

  Thors, Lina ^a   Fowler, Christopher J ^a  

^a UMEÅ UNIVERSITY   (Sweden)

Author keywords

Anandamide; Arachidonic acid; Endocannabinoid; Fatty acid amide hydrolase; Membrane accumulation; Nitric oxide

Indexed keywords

2 ARACHIDONOYLGLYCEROL; ANANDAMIDE; ARACHIDONIC ACID; CYCLOHEXYLCARBAMIC ACID 3' CARBAMOYLBIPHENYL 3 YL ESTER; ENDOCANNABINOID; ETHANOLAMINE; FATTY ACID AMIDASE; N ACETYL S NITROSOPENICILLAMINE; NITRIC OXIDE; NITRIC OXIDE DONOR; NITROPRUSSIDE SODIUM; PHOSPHOLIPID; TRITIUM;

ANIMAL CELL; ARTICLE; BASOPHIL; CELL LABELING; CELL MEMBRANE; CELL METABOLISM; CELL STRAIN 3T3; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INHIBITION; ESTERIFICATION; FIBROBLAST; HYDROLYSIS; INCUBATION TIME; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; ARACHIDONIC ACIDS; BENZAMIDES; CARBAMATES; CELL LINE; CELL MEMBRANE; CYCLIC N-OXIDES; ENDOCANNABINOIDS; FREE RADICAL SCAVENGERS; GLYCERIDES; IMIDAZOLES; LIPID METABOLISM; MICE; NITRIC OXIDE; NITRIC OXIDE DONORS; PALMITIC ACIDS; POLYUNSATURATED ALKAMIDES; RATS; SIGNAL TRANSDUCTION; TRITIUM;

EID: 70349498806     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2009.08.028     Document Type: Article

References (46)

1. Beltramo M., and Piomelli D. Carrier-mediated transport and enzymatic hydrolysis of the endogenous cannabinoid 2-arachidonylglycerol. NeuroReport 11 (2000) 1231-1235
2. Berkels R., Suerhoff S., Roesen R., and Klaus W. Nitric oxide causes a cGMP-independent intracellular calcium rise in porcine endothelial cells-a paradox?. Microvasc. Res. 59 (2000) 38-44
3. Bisogno T., Maccarrone M., De Petrocellis L., Jarrahian A., Finazzi-Agrò A., Hillard C., and Di Marzo V. The uptake by cells of 2-arachidonoylglycerol, an endogenous agonist of cannabinoid receptors. Eur. J. Biochem. 268 (2001) 1982-1989
4. Blankman J.L., Simon G.M., and Cravatt B.F. A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol. Chem. Biol. 14 (2007) 1347-1356
5. Bligh E.G., and Dyer W.J. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37 (1959) 911-917
6. Boldrup L., Wilson S.J., Barbier A.J., and Fowler C.J. A simple stopped assay for fatty acid amide hydrolase avoiding the use of a chloroform extraction phase. J. Biochem. Biophys. Methods 60 (2004) 171-177
7. Chalimoniuk M., Głowacka J., Zabielna A., Eckert A., and Strosznajder J.B. Nitric oxide alters arachidonic acid turnover in brain cortex synaptoneurosomes. Neurochem. Int. 48 (2006) 1-8
8. Chen P., Hu S., Harmon S.D., Moore S.A., Spector A.A., and Fang X. Metabolism of anandamide in cerebral microvascular endothelial cells. Prostaglandins Oth. Lipid Med. 73 (2004) 59-72
9. Day T.A., Rakhshan F., Deutsch D.G., and Barker E.L. Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide. Mol. Pharmacol. 59 (2001) 1369-1375
10. Deutsch D.G., and Chin S.A. Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem. Pharmacol. 46 (1993) 791-796
11. Deutsch D.G., Glaser S.T., Howell J.M., Kunz J.S., Puffenbarger R.A., Hillard C.J., and Abumrad N. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. J. Biol. Chem. 276 (2001) 6967-6973
12. Di Marzo V., Fontana A., Cadas H., Schinelli S., Cimino G., Schwartz J.-C., and Piomelli D. Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature. 372 (1994) 686-691
13. Di Marzo V., Bisogno T., Sugiura T., Melck D., and De Petrocellis L. The novel endogenous cannabinoid 2-arachidonoylglycerol is inactivated by neuronal- and basophil-like cells: connections with anandamide. Biochem. J. 331 (1998) 15-19
14. Di Marzo V., Bisogno T., De Petrocellis L., Melck D., Orlando P., Wagner J.A., and Kunos G. Biosynthesis and inactivation of the endocannabinoid 2-arachidonoylglycerol in circulating and tumoral macrophages. Eur. J. Biochem. 264 (1999) 258-267
15. Di Pasquale E., Chahinian H., Sanchez P., and Fantini J. The insertion and transport of anandamide in synthetic lipid membranes are both cholesterol-dependent. PLoS ONE 4 (2009) e4989
16. Dinh T.P., Carpenter D., Leslie F.M., Freund T.F., Katona I., Sensi S.L., Kathuria S., and Piomelli D. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci U S A 99 (2002) 10819-10824
17. Feil R., and Kleppisch T. NO/cGMP-dependent modulation of synaptic transmission. Handb. Exp. Pharmacol. 184 (2008) 529-560
18. Fowler C.J., and Jacobsson S.O.P. Cellular transport of anandamide, 2-arachidonoylglycerol and palmitoylethanolamide-targets for drug development?. Prostaglandins Leukot. Essent. Fatty Acids 66 (2002) 193-200
19. Fowler C.J., and Ghafouri N. Does the hydrolysis of 2-arachidonoylglycerol regulate its cellular uptake?. Pharmacol. Res. 58 (2008) 72-76
20. Goparaju S.K., Ueda N., Yamaguchi H., and Yamamoto S. Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand. FEBS Lett. 422 (1998) 69-73
21. Hillard C.J., and Jarrahian A. Cellular accumulation of anandamide: consensus and controversy. Br. J. Pharmacol. 140 (2003) 802-808
22. Hillard C.J., and Jarrahian A. Accumulation of anandamide: evidence for cellular diversity. Neuropharmacology 48 (2005) 1072-1078
23. Hogg N., Darley-Usmar V.M., Wilson M.T., and Moncada S. Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide. Biochem. J. 281 (1992) 419-424
24. Jayamanne A., Greenwood R., Mitchell V.A., Aslan S., Piomelli D., and Vaughan C.W. Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models. Br. J. Pharmacol. 147 (2006) 281-288
25. Kaczocha M., Glaser S.T., and Deutsch D.G. Identification of intracellular carriers for the endocannabinoid anandamide. Proc. Natl. Scad. Sci. U.S.A. 106 (2009) 6375-6380
26. Kathuria S., Gaetani S., Fegley D., Valiño F., Duranti A., Tontini A., Mor M., Tarzia G., La Rana G., Calignano A., Giustino A., Tattoli M., Palmery M., Cuomo V., and Piomelli D. Modulation of anxiety through blockade of anandamide hydrolysis. Nat. Med. 9 (2003) 76-81
27. Long J.Z., Li W., Booker L., Burston J.J., Kinsey S.G., Schlosburg J.E., Pavón F.J., Serrano A.M., Selley D.E., Parsons L.H., Lichtman A.H., and Cravatt B.F. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat. Chem. Biol. 5 (2009) 37-44
28. Maccarrone M., Bari M., Lorenzon T., Bisogno T., Di Marzo V., and Finazzi-Agrò A. Anandamide uptake by human endothelial cells and its regulation by nitric oxide. J. Biol. Chem. 275 (2000) 13484-13492
29. Maccarrone M., Fiori A., Bari M., Granata F., Gasperi V., De Stefano M.E., Finazzi-Agrò A., and Strom R. Regulation by cannabinoid receptors of anandamide transport across the blood-brain barrier and through other endothelial cells. Thromb. Haemost. 95 (2006) 117-127
30. Maragos C.M., Morley D., Wink D.A., Dunams T.M., Saavedra J.E., Hoffman A., Bove A.A., Isaac L., Hrabie J.A., and Keefer L.K. Complexes of .NO with nucleophiles as agents for the controlled biological release of nitric oxide. Vasorelaxant effects. J. Med. Chem. 34 (1991) 3242-3247
31. McFarland M.J., Porter A.C., Rakhshan F.R., Rawat D.S., Gibbs R.A., and Barker E.L. A role for caveolae/lipid rafts in the uptake and recycling of the endogenous cannabinoid anandamide. J. Biol. Chem. 279 (2004) 41991-41997
32. Nguyen T., Brunson D., Crespi C.L., Penman B.W., Wishnok J.S., and Tannenbaum S.R. DNA damage and mutation in human cells exposed to nitric oxide in vitro. Proc Natl Acad Sci U S A 89 (1992) 3030-3034
33. Oddi S., Fezza F., Pasquariello N., De Simone C., Rapino C., Dainese E., Finazzi-Agrò A., and Maccarrone M. Evidence for the intracellular accumulation of anandamide in adiposomes. Cell. Mol. Life Sci. 65 (2008) 840-850
34. Oddi S., Fezza F., Pasquariello N., D'Agostino A., Catanzaro G., De Simone C., Rapino C., Finazzi-Agrò A., and Maccarrone M. Molecular identification of albumin and Hsp70 as cytosolic anandamide-binding proteins. Chem. Biol. 16 (2009) 624-632
35. Pacher P., Bátkai S., and Kunos G. The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol. Rev. 58 (2006) 389-462
36. Placzek E.A., Okamoto Y., Ueda N., and Barker E.L. Mechanisms for recycling and biosynthesis of endogenous cannabinoids anandamide and 2-arachidonylglycerol. J. Neurochem. 107 (2008) 987-1000
37. Rimmerman N., Hughes H.V., Bradshaw H.B., Pazos M.X., Mackie K., Prieto A.L., and Walker J.M. Compartmentalization of endocannabinoids into lipid rafts in a dorsal root ganglion cell line. Br. J. Pharmacol. 153 (2008) 380-389
38. Sakuma S., Fujimoto Y., Katoh Y., and Fujita T. The effects of nitric oxide and peroxynitrite on the formation of prostaglandin and arachidonoyl-CoA formed from arachidonic acid in rabbit kidney medulla microsomes. Prostaglandins Leukot. Essent. Fatty Acids 68 (2003) 343-349
39. Shen J., Lee W., Li Y., Lau C.F., Ng K.M., Fung M.L., and Liu K.J. Interaction of caveolin-1, nitric oxide, and nitric oxide synthases in hypoxic human SK-N-MC neuroblastoma cells. J. Neurochem. 107 (2008) 478-487
40. Stefano G.B., Liu Y., and Goligorsky M.S. Cannabinoid receptors are coupled to nitric oxide release in invertebrate immunocytes, microglia, and human monocytes. J. Biol. Chem. 271 (1996) 19238-19242
41. Stefano G.B., Bilfinger T.V., Rialas C.M., and Deutsch D.G. 2-Arachidonyl-glycerol stimulates nitric oxide release from human immune and vascular tissues and invertebrate immunocytes by cannabinoid receptor 1. Pharmacol. Res. 42 (2000) 317-322
42. Thors L., Eriksson J., and Fowler C.J. Inhibition of the cellular uptake of anandamide by genistein and its analogue daidzein in cells with different levels of fatty acid amide hydrolase-driven uptake. Br. J. Pharmacol. 152 (2007) 744-750
43. Thors L., Belghiti M., and Fowler C.J. Inhibition of fatty acid amide hydrolase by kaempferol and related naturally occurring flavonoids. Br. J. Pharmacol. 155 (2008) 244-252
44. Trigatti B.L., Anderson R.G.W., and Gerber G.E. Identification of caveolin-1 as a fatty acid binding protein. Biochem. Biophys. Res. Commun. 255 (1999) 34-39
45. Wanstall J.C., Jeffery T.K., Gambino A., Lovren F., and Triggle C.R. Vascular smooth muscle relaxation mediated by nitric oxide donors: a comparison with acetylcholine, nitric oxide and nitroxyl ion. Br. J. Pharmacol. 134 (2001) 463-472
46. 2α through nitric oxide-induced S-nitrosylation. Involvement of inducible nitric-oxide synthase and cyclooxygenase-2. J. Biol. Chem. 283 (2008) 3077-3087