Anandamide transport

Pharmacology and Therapeutics

Volumn 104, Issue 2, 2004, Pages 117-135

  McFarland, Matthew J ^a   Barker, Eric L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

9 Tetrahydorcannabinol; Amidohydrolyase; Anandamide; Cannabinoid; Marijuana; Transporter

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; ANANDAMIDE; ARACHIDONIC ACID; CANNABINOID RECEPTOR AGONIST; CANNABINOID RECEPTOR ANTAGONIST; DIZOCILPINE; DRONABINOL; FATTY ACID AMIDASE; N (4 HYDROXYPHENYL)ARACHIDONAMIDE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; NABILONE; RHODAMINE; RIMONABANT; UNCLASSIFIED DRUG; VIRODHAMINE;

ANXIETY; CENTRAL NERVOUS SYSTEM; DISEASE ASSOCIATION; DRUG EFFECT; DRUG INHIBITION; DRUG METABOLISM; DRUG SYNTHESIS; DRUG TRANSPORT; DRUG UPTAKE; HUMAN; IN VIVO STUDY; KNOCKOUT MOUSE; NONHUMAN; PRIORITY JOURNAL; REVIEW; SIGNAL TRANSDUCTION; SPASTICITY;

ANIMALS; ARACHIDONIC ACIDS; BIOLOGICAL TRANSPORT; CANNABINOIDS; HUMANS; POLYUNSATURATED ALKAMIDES; RECEPTORS, CANNABINOID;

EID: 7044270770     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.pharmthera.2004.07.008     Document Type: Review

References (155)

1. T. Aoki, R. Nomura, and T. Fujimoto Tyrosine phosphorylation of caveolin-1 in the endothelium Exp Cell Res 253 2 1999 629 636
2. D. Baker, G. Pryce, J.L. Croxford, P. Brown, R.G. Pertwee, and J.W. Huffman Cannabinoids control spasticity and tremor in a multiple sclerosis model Nature 404 6773 2000 84 87
3. D. Baker, G. Pryce, J.L. Croxford, P. Brown, R.G. Pertwee, and A. Makriyannis Endocannabinoids control spasticity in a multiple sclerosis model FASEB J 15 2 2001 300 302
4. M. Beltramo, and D. Piomelli Anandamide transport inhibition by the vanilloid agonist olvanil Eur J Pharmacol 364 1 1999 75 78
5. M. Beltramo, N. Stella, A. Calignano, S.Y. Lin, A. Makriyannis, and D. Piomelli Functional role of high-affinity anandamide transport, as revealed by selective inhibition Science 277 5329 1997 1094 1097
6. M. Beltramo, F.R. de Fonseca, M. Navarro, A. Calignano, M.A. Gorriti, and G. Grammatikopoulos Reversal of dopamine D(2) receptor responses by an anandamide transport inhibitor J Neurosci 20 9 2000 3401 3407
7. F. Berrendero, and R. Maldonado Involvement of the opioid system in the anxiolytic-like effects induced by Delta(9)-tetrahydrocannabinol Psychopharmacology (Berl) 163 1 2002 111 117
8. T. Bisogno, S. Maurelli, D. Melck, L. De Petrocellis, and V. Di Marzo Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes J Biol Chem 272 6 1997 3315 3323
9. M.H. Bracey, M.A. Hanson, K.R. Masuda, R.C. Stevens, and B.F. Cravatt Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling Science 298 5599 2002 1793 1796
10. C.S. Breivogel, G. Griffin, V. Di Marzo, and B.R. Martin Evidence for a new G protein-coupled cannabinoid receptor in mouse brain Mol Pharmacol 60 1 2001 155 163
11. D.A. Brown, and E. London Structure and function of sphingolipid- and cholesterol-rich membrane rafts J Biol Chem 275 23 2000 17221 17224
12. G.A. Cabral, D.M. Toney, K. Fischer-Stenger, M.P. Harrison, and F. Marciano-Cabral Anandamide inhibits macrophage-mediated killing of tumor necrosis factor-sensitive cells Life Sci 56 23-24 1995 2065 2072
13. H. Cadas, E. di Tomaso, and D. Piomelli Occurrence and biosynthesis of endogenous cannabinoid precursor, N-arachidonoyl phosphatidylethanolamine, in rat brain J Neurosci 17 4 1997 1226 1242
14. A. Calignano, G. La Rana, M. Beltramo, A. Makriyannis, and D. Piomelli Potentiation of anandamide hypotension by the transport inhibitor, AM404 Eur J Pharmacol 337 1 1997 R1 R2
15. P.L. Cameron, J.W. Ruffin, R. Bollag, H. Rasmussen, and R.S. Cameron Identification of caveolin and caveolin-related proteins in the brain J Neurosci 17 24 1997 9520 9535
16. D. Centonze, N. Battista, S. Rossi, N.B. Mercuri, A. Finazzi-Agro, and G. Bernardi A critical interaction between dopamine D2 receptors and endocannabinoids mediates the effects of cocaine on striatal GABAergic transmission Neuropsychopharmacology 2004
17. S.R. Childers, T. Sexton, and M.B. Roy Effects of anandamide on cannabinoid receptors in rat brain membranes Biochem Pharmacol 47 4 1994 711 715
18. A.B. Clement, E.G. Hawkins, A.H. Lichtman, and B.F. Cravatt Increased seizure susceptibility and proconvulsant activity of anandamide in mice lacking fatty acid amide hydrolase J Neurosci 23 9 2003 3916 3923
19. C. Collin, W.A. Devane, D. Dahl, C.J. Lee, J. Axelrod, and D.L. Alkon Long-term synaptic transformation of hippocampal CA1 gamma-aminobutyric acid synapses and the effect of anandamide Proc Natl Acad Sci U S A 92 22 1995 10167 10171
20. B.F. Cravatt, and A.H. Lichtman Fatty acid amide hydrolase: an emerging therapeutic target in the endocannabinoid system Curr Opin Chem Biol 7 4 2003 469 475
21. B.F. Cravatt, O. Prospero-Garcia, G. Siuzdak, N.B. Gilula, S.J. Henriksen, and D.L. Boger Chemical characterization of a family of brain lipids that induce sleep Science 268 5216 1995 1506 1509
22. B.F. Cravatt, D.K. Giang, S.P. Mayfield, D.L. Boger, R.A. Lerner, and N.B. Gilula Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides Nature 384 6604 1996 83 87
23. B.F. Cravatt, K. Demarest, M.P. Patricelli, M.H. Bracey, D.K. Giang, and B.R. Martin Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase Proc Natl Acad Sci U S A 98 16 2001 9371 9376
24. J.N. Crawley, R.L. Corwin, J.K. Robinson, C.C. Felder, W.A. Devane, and J. Axelrod Anandamide, an endogenous ligand of the cannabinoid receptor, induces hypomotility and hypothermia in vivo in rodents Pharmacol Biochem Behav 46 4 1993 967 972
25. T.A. Day, F. Rakhshan, D.G. Deutsch, and E.L. Barker Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide Mol Pharmacol 59 6 2001 1369 1375
26. E. de Lago, A. Ligresti, G. Ortar, E. Morera, A. Cabranes, and G. Pryce In vivo pharmacological actions of two novel inhibitors of anandamide cellular uptake Eur J Pharmacol 484 2-3 2004 249 257
27. N. De Marchi, L. De Petrocellis, P. Orlando, F. Daniele, F. Fezza, and V. Di Marzo Endocannabinoid signalling in the blood of patients with schizophrenia Lipids Health Dis 2 1 2003 5
28. L. De Petrocellis, T. Bisogno, J.B. Davis, R.G. Pertwee, and V. Di Marzo Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity FEBS Lett 483 1 2000 52 56
29. L. De Petrocellis, T. Bisogno, M. Maccarrone, J.B. Davis, A. Finazzi-Agro, and V. Di Marzo The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism J Biol Chem 276 16 2001 12856 12863
30. L. De Petrocellis, T. Bisogno, A. Ligresti, M. Bifulco, D. Melck, and V. Di Marzo Effect on cancer cell proliferation of palmitoylethanolamide, a fatty acid amide interacting with both the cannabinoid and vanilloid signalling systems Fundam Clin Pharmacol 16 4 2002 297 302
31. F. Desarnaud, H. Cadas, and D. Piomelli Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization J Biol Chem 270 11 1995 6030 6035
32. D.G. Deutsch, and S.A. Chin Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist Biochem Pharmacol 46 5 1993 791 796
33. D.G. Deutsch, S.T. Glaser, J.M. Howell, J.S. Kunz, R.A. Puffenbarger, and C.J. Hillard The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase J Biol Chem 276 10 2001 6967 6973
34. W.A. Devane, L. Hanus, A. Breuer, R.G. Pertwee, L.A. Stevenson, and G. Griffin Isolation and structure of a brain constituent that binds to the cannabinoid receptor Science 258 5090 1992 1946 1949
35. G. Di Carlo, and A.A. Izzo Cannabinoids for gastrointestinal diseases: potential therapeutic applications Expert Opin Investig Drugs 12 1 2003 39 49
36. V. Di Marzo 'Endocannabinoids' and other fatty acid derivatives with cannabimimetic properties: biochemistry and possible physiopathological relevance Biochim Biophys Acta 1392 2-3 1998 153 175
37. V. Di Marzo, A. Fontana, H. Cadas, S. Schinelli, G. Cimino, and J.C. Schwartz Formation and inactivation of endogenous cannabinoid anandamide in central neurons Nature 372 6507 1994 686 691
38. V. Di Marzo, T. Bisogno, T. Sugiura, D. Melck, and L. De Petrocellis The novel endogenous cannabinoid 2-arachidonoylglycerol is inactivated by neuronal- and basophil-like cells: connections with anandamide Biochem J 331 Pt. 1 1998 15 19
39. V. Di Marzo, T. Bisogno, and L. De Petrocellis Anandamide: some like it hot Trends Pharmacol Sci 22 7 2001 346 349
40. V. Di Marzo, G. Griffin, L. De Petrocellis, I. Brandi, T. Bisogno, and W. Williams A structure/activity relationship study on arvanil, an endocannabinoid and vanilloid hybrid J Pharmacol Exp Ther 300 3 2002 984 991
41. T.P. Dinh, D. Carpenter, F.M. Leslie, T.F. Freund, I. Katona, and S.L. Sensi Brain monoglyceride lipase participating in endocannabinoid inactivation Proc Natl Acad Sci U S A 99 16 2002 10819 10824
42. M. Egertova, D.K. Giang, B.F. Cravatt, and M.R. Elphick A new perspective on cannabinoid signalling: complementary localization of fatty acid amide hydrolase and the CB1 receptor in rat brain Proc R Soc Lond B Biol Sci 265 1410 1998 2081 2085
43. L. Facci, R. Dal Toso, S. Romanello, A. Buriani, S.D. Skaper, and A. Leon Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide Proc Natl Acad Sci U S A 92 8 1995 3376 3380
44. A.A. Farooqui, W.A. Taylor, and L.A. Horrocks Characterization and solubilization of membrane bound diacylglycerol lipases from bovine brain Int J Biochem 18 11 1986 991 997
45. D. Fegley, S. Kathuria, R. Mercier, C. Li, A. Goutopoulos, and A. Makriyannis Anandamide transport is independent of fatty-acid amide hydrolase activity and is blocked by the hydrolysis-resistant inhibitor AM1172 Proc Natl Acad Sci U S A 2004
46. C.C. Felder, J.S. Veluz, H.L. Williams, E.M. Briley, and L.A. Matsuda Cannabinoid agonists stimulate both receptor- and non-receptor-mediated signal transduction pathways in cells transfected with and expressing cannabinoid receptor clones Mol Pharmacol 42 5 1992 838 845
47. C.C. Felder, E.M. Briley, J. Axelrod, J.T. Simpson, K. Mackie, and W.A. Devane 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 90 16 1993 7656 7660
48. C.C. Felder, K.E. Joyce, E.M. Briley, J. Mansouri, K. Mackie, and O. Blond Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors Mol Pharmacol 48 3 1995 443 450
49. A. Fontana, V. Di Marzo, H. Cadas, and D. Piomelli Analysis of anandamide, an endogenous cannabinoid substance, and of other natural N-acylethanolamines Prostaglandins Leukot Essent Fat Acids 53 4 1995 301 308
50. T.F. Freund, I. Katona, and D. Piomelli Role of endogenous cannabinoids in synaptic signaling Physiol Rev 83 3 2003 1017 1066
51. E. Fride, and R. Mechoulam Pharmacological activity of the cannabinoid receptor agonist, anandamide, a brain constituent Eur J Pharmacol 231 2 1993 313 314
52. M. Fritzsche Are cannabinoid receptor knockout mice animal models for schizophrenia? Med Hypotheses 56 6 2001 638 643
53. S. Gaetani, V. Cuomo, and D. Piomelli Anandamide hydrolysis: a new target for anti-anxiety drugs? Trends Mol Med 9 11 2003 474 478
54. Y. Gaoni, and R. Mechoulam The isolation and structure of delta-1-tetrahydrocannabinol and other neutral cannabinoids from hashish J Am Chem Soc 93 1 1971 217 224
55. G.L. Gerdeman, J. Ronesi, and D.M. Lovinger Postsynaptic endocannabinoid release is critical to long-term depression in the striatum Nat Neurosci 5 5 2002 446 451
56. D.K. Giang, and B.F. Cravatt Molecular characterization of human and mouse fatty acid amide hydrolases Proc Natl Acad Sci U S A 94 6 1997 2238 2242
57. A. Giuffrida, L.H. Parsons, T.M. Kerr, F. Rodriguez de Fonseca, M. Navarro, and D. Piomelli Dopamine activation of endogenous cannabinoid signaling in dorsal striatum Nat Neurosci 2 4 1999 358 363
58. S.T. Glaser, N.A. Abumrad, F. Fatade, M. Kaczocha, K.M. Studholme, and D.G. Deutsch Evidence against the presence of an anandamide transporter Proc Natl Acad Sci U S A 100 7 2003 4269 4274
59. M. Glass, and C.C. Felder Concurrent stimulation of cannabinoid CB1 and dopamine D2 receptors augments cAMP accumulation in striatal neurons: evidence for a Gs linkage to the CB1 receptor J Neurosci 17 14 1997 5327 5333
60. S. Gonzalez, J. Romero, R. de Miguel, I. Lastres-Becker, M.A. Villanua, and A. Makriyannis Extrapyramidal and neuroendocrine effects of AM404, an inhibitor of the carrier-mediated transport of anandamide Life Sci 65 3 1999 327 336
61. S.K. Goparaju, N. Ueda, H. Yamaguchi, and S. Yamamoto Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand FEBS Lett 422 1 1998 69 73
62. N. Hajos, C. Ledent, and T.F. Freund Novel cannabinoid-sensitive receptor mediates inhibition of glutamatergic synaptic transmission in the hippocampus Neuroscience 106 1 2001 1 4
63. L. Hanus, A. Gopher, S. Almog, and R. Mechoulam Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor J Med Chem 36 20 1993 3032 3034
64. L. Hanus, S. Abu-Lafi, E. Fride, A. Breuer, Z. Vogel, and D.E. Shalev 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor Proc Natl Acad Sci U S A 98 7 2001 3662 3665
65. R.J. Helliwell, L.M. McLatchie, M. Clarke, J. Winter, S. Bevan, and P. McIntyre Capsaicin sensitivity is associated with the expression of the vanilloid (capsaicin) receptor (VR1) mRNA in adult rat sensory ganglia Neurosci Lett 250 3 1998 177 180
66. M. Herkenham, A.B. Lynn, M.D. Little, M.R. Johnson, L.S. Melvin, and B.R. de Costa Cannabinoid receptor localization in brain Proc Natl Acad Sci U S A 87 5 1990 1932 1936
67. M. Herkenham, A.B. Lynn, B.R. de Costa, and E.K. Richfield Neuronal localization of cannabinoid receptors in the basal ganglia of the rat Brain Res 547 2 1991 267 274
68. C.J. Hillard, and A. Jarrahian The movement of N-arachidonoylethanolamine (anandamide) across cellular membranes Chem Phys Lipids 108 1-2 2000 123 134
69. C.J. Hillard, and A. Jarrahian Cellular accumulation of anandamide: consensus and controversy Br J Pharmacol 140 5 2003 802 808
70. C.J. Hillard, W.S. Edgemond, A. Jarrahian, and W.B. Campbell Accumulation of N-arachidonoylethanolamine (anandamide) into cerebellar granule cells occurs via facilitated diffusion J Neurochem 69 2 1997 631 638
71. A.C. Howlett Pharmacology of cannabinoid receptors Annu Rev Pharmacol Toxicol 35 1995 607 634
72. E.J. Ishac, L. Jiang, K.D. Lake, K. Varga, M.E. Abood, and G. Kunos Inhibition of exocytotic noradrenaline release by presynaptic cannabinoid CB1 receptors on peripheral sympathetic nerves Br J Pharmacol 118 8 1996 2023 2028
73. A. Jarrahian, S. Manna, W.S. Edgemond, W.B. Campbell, and C.J. Hillard Structure-activity relationships among N-arachidonylethanolamine (anandamide) head group analogues for the anandamide transporter J Neurochem 74 6 2000 2597 2606
74. A. Jarrahian, V.J. Watts, and E.L. Barker D2 dopamine receptors modulate G alpha-subunit coupling of the CB1 cannabinoid receptor J Pharmacol Exp Ther 308 3 2004 880 886
75. J.C. Jerman, J. Gray, S.J. Brough, L. Ooi, D. Owen, and J.B. Davis Comparison of effects of anandamide at recombinant and endogenous rat vanilloid receptors Br J Anaesth 89 6 2002 882 887
76. L. Johannes, and C. Lamaze Clathrin-dependent or not: is it still the question? Traffic 3 7 2002 443 451
77. D.E. Johnson, S.L. Heald, R.D. Dally, and R.A. Janis Isolation, identification and synthesis of an endogenous arachidonic amide that inhibits calcium channel antagonist 1,4-dihydropyridine binding Prostaglandins Leukot Essent Fat Acids 48 6 1993 429 437
78. K.O. Jonsson, S. Vandevoorde, D.M. Lambert, G. Tiger, and C.J. Fowler Effects of homologues and analogues of palmitoylethanolamide upon the inactivation of the endocannabinoid anandamide Br J Pharmacol 133 8 2001 1263 1275
79. N. Kanai, R. Lu, J.A. Satriano, Y. Bao, A.W. Wolkoff, and V.L. Schuster Identification and characterization of a prostaglandin transporter Science 268 5212 1995 866 869
80. S. Kathuria, S. Gaetani, D. Fegley, F. Valino, A. Duranti, and A. Tontini Modulation of anxiety through blockade of anandamide hydrolysis Nat Med 9 1 2003 76 81
81. A.D. Khanolkar, and A. Makriyannis Structure-activity relationships of anandamide, an endogenous cannabinoid ligand Life Sci 65 6-7 1999 607 616
82. F.A. Kuehl, T.A. Jacob, O.H. Ganley, R.E. Orm, and M.A.P. Meisinger Anti-inflammatory actions of palmitoylethanolamide J Am Chem Soc 79 1957 5577 5579
83. D.M. Lambert, and V. Di Marzo The palmitoylethanolamide and oleamide enigmas: are these two fatty acid amides cannabimimetic? Curr Med Chem 6 8 1999 757 773
84. A.H. Lichtman, E.G. Hawkins, G. Griffin, and B.F. Cravatt Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo J Pharmacol Exp Ther 302 1 2002 73 79
85. A. Ligresti, E. Morera, M.M. Van Der Stelt, K. Monory, B. Lutz, and G. Ortar Further evidence for the existence of a specific process for the membrane transport of anandamide Biochem J 2004 (Pt)
86. M.L. Lopez-Rodriguez, A. Viso, S. Ortega-Gutierrez, C.J. Fowler, G. Tiger, and E. de Lago Design, synthesis and biological evaluation of new endocannabinoid transporter inhibitors Eur J Med Chem 38 4 2003 403 412
87. M.L. Lopez-Rodriguez, A. Viso, S. Ortega-Gutierrez, C.J. Fowler, G. Tiger, and E. de Lago Design, synthesis, and biological evaluation of new inhibitors of the endocannabinoid uptake: comparison with effects on fatty acid amidohydrolase J Med Chem 46 8 2003 1512 1522
88. A.B. Lynn, and M. Herkenham Localization of cannabinoid receptors and nonsaturable high-density cannabinoid binding sites in peripheral tissues of the rat: implications for receptor-mediated immune modulation by cannabinoids J Pharmacol Exp Ther 268 3 1994 1612 1623
89. M. Maccarrone, M. van der Stelt, A. Rossi, G.A. Veldink, J.F. Vliegenthart, and A.F. Agro Anandamide hydrolysis by human cells in culture and brain J Biol Chem 273 48 1998 32332 32339
90. M. Maccarrone, M. Bari, T. Lorenzon, T. Bisogno, V. Di Marzo, and A. Finazzi-Agro Anandamide uptake by human endothelial cells and its regulation by nitric oxide J Biol Chem 275 18 2000 13484 13492
91. M. Maccarrone, M. Bari, N. Battista, and A. Finazzi-Agro Estrogen stimulates arachidonoylethanolamide release from human endothelial cells and platelet activation Blood 100 12 2002 4040 4048
92. K. Mackie, W.A. Devane, and B. Hille Anandamide, an endogenous cannabinoid, inhibits calcium currents as a partial agonist in N18 neuroblastoma cells Mol Pharmacol 44 3 1993 498 503
93. K. Mackie, Y. Lai, R. Westenbroek, and R. Mitchell Cannabinoids activate an inwardly rectifying potassium conductance and inhibit Q-type calcium currents in AtT20 cells transfected with rat brain cannabinoid receptor J Neurosci 15 10 1995 6552 6561
94. P. Mailleux, and J.J. Vanderhaeghen Dopaminergic regulation of cannabinoid receptor mRNA levels in the rat caudate-putamen: an in situ hybridization study J Neurochem 61 5 1993 1705 1712
95. L.A. Matsuda, S.J. Lolait, M.J. Brownstein, A.C. Young, and T.I. Bonner Structure of a cannabinoid receptor and functional expression of the cloned cDNA Nature 346 6284 1990 561 564
96. L.A. Matsuda, T.I. Bonner, and S.J. Lolait Localization of cannabinoid receptor mRNA in rat brain J Comp Neurol 327 4 1993 535 550
97. S. Maurelli, T. Bisogno, L. De Petrocellis, A. Di Luccia, G. Marino, and V. Di Marzo Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase' FEBS Lett 377 1 1995 82 86
98. M.J. McFarland, A.C. Porter, and E.L. Barker Uptake of the endogenous cannabinoid anandamide by endocytic processes and accumulation in lipid rafts Exp Biol 2003 (Abstract 395.9)
99. M.J. McFarland, F.R. Rakhshan, J.L. Wilson, and E.L. Barker Endocytic and cellular trafficking processes involved with uptake and metabolism of anandamide Exp Biol 2004 (Abstract 397.8)
100. R. Mechoulam, S. Ben-Shabat, L. Hanus, M. Ligumsky, N.E. Kaminski, and A.R. Schatz Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors Biochem Pharmacol 50 1 1995 83 90
101. D. Melck, T. Bisogno, L. De Petrocellis, H. Chuang, D. Julius, and M. Bifulco Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors Biochem Biophys Res Commun 262 1 1999 275 284
102. D. Melck, L. De Petrocellis, P. Orlando, T. Bisogno, C. Laezza, and M. Bifulco Suppression of nerve growth factor Trk receptors and prolactin receptors by endocannabinoids leads to inhibition of human breast and prostate cancer cell proliferation Endocrinology 141 1 2000 118 126
103. M. Mimeault, N. Pommery, N. Wattez, C. Bailly, and J.P. Henichart Anti-proliferative and apoptotic effects of anandamide in human prostatic cancer cell lines: implication of epidermal growth factor receptor down-regulation and ceramide production Prostate 56 1 2003 1 12
104. S. Munro, K.L. Thomas, and M. Abu-Shaar Molecular characterization of a peripheral receptor for cannabinoids Nature 365 6441 1993 61 65
105. Y. Okamoto, J. Morishita, K. Tsuboi, T. Tonai, and N. Ueda Molecular characterization of a phospholipase D generating anandamide and its congeners J Biol Chem 279 7 2004 5298 5305
106. G. Ortar, A. Ligresti, L. De Petrocellis, E. Morera, and V. Di Marzo Novel selective and metabolically stable inhibitors of anandamide cellular uptake Biochem Pharmacol 65 9 2003 1473 1481
107. L. Pelkmans, J. Kartenbeck, and A. Helenius Caveolar endocytosis of simian virus 40 reveals a new two-step vesicular-transport pathway to the ER Nat Cell Biol 3 5 2001 473 483
108. R. Pertwee, G. Griffin, L. Hanus, and R. Mechoulam Effects of two endogenous fatty acid ethanolamides on mouse vasa deferentia Eur J Pharmacol 259 2 1994 115 120
109. G. Petersen, and H.S. Hansen N-Acylphosphatidylethanolamine-hydrolysing phospholipase D lacks the ability to transphosphatidylate FEBS Lett 455 1-2 1999 41 44
110. L.J. Pike, X. Han, K.N. Chung, and R.W. Gross Lipid rafts are enriched in arachidonic acid and plasmenylethanolamine and their composition is independent of caveolin-1 expression: a quantitative electrospray ionization/mass spectrometric analysis Biochemistry 41 6 2002 2075 2088
111. J.C. Pinto, F. Potie, K.C. Rice, D. Boring, M.R. Johnson, and D.M. Evans Cannabinoid receptor binding and agonist activity of amides and esters of arachidonic acid Mol Pharmacol 46 3 1994 516 522
112. D. Piomelli The ligand that came from within Trends Pharmacol Sci 22 1 2001 17 19
113. D. Piomelli, M. Beltramo, S. Glasnapp, S.Y. Lin, A. Goutopoulos, and X.Q. Xie Structural determinants for recognition and translocation by the anandamide transporter Proc Natl Acad Sci U S A 96 10 1999 5802 5807
114. D. Piomelli, A. Giuffrida, A. Calignano, and F. Rodriguez de Fonseca The endocannabinoid system as a target for therapeutic drugs Trends Pharmacol Sci 21 6 2000 218 224
115. A.C. Porter, J.M. Sauer, M.D. Knierman, G.W. Becker, M.J. Berna, and J. Bao Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor J Pharmacol Exp Ther 301 3 2002 1020 1024
116. V. Puri, R. Watanabe, R.D. Singh, M. Dominguez, J.C. Brown, and C.L. Wheatley Clathrin-dependent and -independent internalization of plasma membrane sphingolipids initiates two Golgi targeting pathways J Cell Biol 154 3 2001 535 547
117. F. Rakhshan, T.A. Day, R.D. Blakely, and E.L. Barker Carrier-mediated uptake of the endogenous cannabinoid anandamide in RBL-2H3 cells J Pharmacol Exp Ther 292 3 2000 960 967
118. B. Razani, S.E. Woodman, and M.P. Lisanti Caveolae: from cell biology to animal physiology Pharmacol Rev 54 3 2002 431 467
119. P.H. Reggio, and H. Traore Conformational requirements for endocannabinoid interaction with the cannabinoid receptors, the anandamide transporter and fatty acid amidohydrolase Chem Phys Lipids 108 1-2 2000 15 35
120. J.D. Richardson, L. Aanonsen, and K.M. Hargreaves SR 141716A, a cannabinoid receptor antagonist, produces hyperalgesia in untreated mice Eur J Pharmacol 319 2-3 1997 R3 R4
121. J.D. Richardson, L. Aanonsen, and K.M. Hargreaves Hypoactivity of the spinal cannabinoid system results in NMDA-dependent hyperalgesia J Neurosci 18 1 1998 451 457
122. J. Romero, R. de Miguel, J.A. Ramos, and J.J. Fernandez-Ruiz The activation of cannabinoid receptors in striatonigral GABAergic neurons inhibited GABA uptake Life Sci 62 4 1998 351 363
123. S.H. Roth, and P.J. Williams The non-specific membrane binding properties of delta9-tetrahydrocannabinol and the effects of various solubilizers J Pharm Pharmacol 31 4 1979 224 230
124. L. Ruiz-Llorente, S. Ortega-Gutierrez, A. Viso, M.G. Sanchez, A.M. Sanchez, and C. Fernandez Characterization of an anandamide degradation system in prostate epithelial PC-3 cells: synthesis of new transporter inhibitors as tools for this study Br J Pharmacol 141 3 2004 457 467
125. M.G. Sanchez, L. Ruiz-Llorente, A.M. Sanchez, and I. Diaz-Laviada Activation of phosphoinositide 3-kinase/PKB pathway by CB(1) and CB(2) cannabinoid receptors expressed in prostate PC-3 cells. Involvement in Raf-1 stimulation and NGF induction Cell Signal 15 9 2003 851 859
126. K.P. Sarker, and I. Maruyama Anandamide induces cell death independently of cannabinoid receptors or vanilloid receptor 1: possible involvement of lipid rafts Cell Mol Life Sci 60 6 2003 1200 1208
127. J.E. Schaffer, and H.F. Lodish Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein Cell 79 3 1994 427 436
128. J.E. Schnitzer, J. Allard, and P. Oh NEM inhibits transcytosis, endocytosis, and capillary permeability: implication of caveolae fusion in endothelia Am J Physiol 268 1 Pt 2 1995 H48 H55
129. W. Schubert, P.G. Frank, B. Razani, D.S. Park, C.W. Chow, and M.P. Lisanti Caveolae-deficient endothelial cells show defects in the uptake and transport of albumin in vivo J Biol Chem 276 52 2001 48619 48622
130. P. Sharma, S. Sabharanjak, and S. Mayor Endocytosis of lipid rafts: an identity crisis Semin Cell Dev Biol 13 3 2002 205 214
131. D.K. Sharma, A. Choudhury, R.D. Singh, C.L. Wheatley, D.L. Marks, and R.E. Pagano Glycosphingolipids internalized via caveolar-related endocytosis rapidly merge with the clathrin pathway in early endosomes and form microdomains for recycling J Biol Chem 278 9 2003 7564 7572
132. D. Smart, K.O. Jonsson, S. Vandevoorde, D.M. Lambert, and C.J. Fowler Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism Br J Pharmacol 136 3 2002 452 458
133. P.B. Smith, D.R. Compton, S.P. Welch, R.K. Razdan, R. Mechoulam, and B.R. Martin The pharmacological activity of anandamide, a putative endogenous cannabinoid, in mice J Pharmacol Exp Ther 270 1 1994 219 227
134. G. Sowa, M. Pypaert, and W.C. Sessa Distinction between signaling mechanisms in lipid rafts vs. caveolae Proc Natl Acad Sci U S A 98 24 2001 14072 14077
135. G.B. Stefano, B. Salzet, C.M. Rialas, M. Pope, A. Kustka, and K. Neenan Morphine- and anandamide-stimulated nitric oxide production inhibits presynaptic dopamine release Brain Res 763 1 1997 63 68
136. N. Stella, P. Schweitzer, and D. Piomelli A second endogenous cannabinoid that modulates long-term potentiation Nature 388 6644 1997 773 778
137. W. Stremmel, L. Pohl, A. Ring, and T. Herrmann A new concept of cellular uptake and intracellular trafficking of long-chain fatty acids Lipids 36 9 2001 981 989
138. T. Sugiura, S. Kondo, A. Sukagawa, S. Nakane, A. Shinoda, and K. Itoh 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain Biochem Biophys Res Commun 215 1 1995 89 97
139. E. Sulcova, R. Mechoulam, and E. Fride Biphasic effects of anandamide Pharmacol Biochem Behav 59 2 1998 347 352
140. 3H]11-OH-delta 9-THC-DMH J Pharmacol Exp Ther 263 3 1992 1383 1390
141. M. Tominaga, and D. Julius Capsaicin receptor in the pain pathway Jpn J Pharmacol 83 1 2000 20 24
142. K. Tsou, M.I. Nogueron, S. Muthian, M.C. Sanudo-Pena, C.J. Hillard, and D.G. Deutsch Fatty acid amide hydrolase is located preferentially in large neurons in the rat central nervous system as revealed by immunohistochemistry Neurosci Lett 254 3 1998 137 140
143. N. Ueda, Y. Kurahashi, S. Yamamoto, and T. Tokunaga Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide J Biol Chem 270 40 1995 23823 23827
144. N. Ueda, R.A. Puffenbarger, S. Yamamoto, and D.G. Deutsch The fatty acid amide hydrolase (FAAH) Chem Phys Lipids 108 1-2 2000 107 121
145. H. Ujike, M. Takaki, K. Nakata, Y. Tanaka, T. Takeda, and M. Kodama CNR1, central cannabinoid receptor gene, associated with susceptibility to hebephrenic schizophrenia Mol Psychiatry 7 5 2002 515 518
146. L. Venance, D. Piomelli, J. Glowinski, and C. Giaume Inhibition by anandamide of gap junctions and intercellular calcium signalling in striatal astrocytes Nature 376 6541 1995 590 594
147. Z. Vogel, J. Barg, R. Levy, D. Saya, E. Heldman, and R. Mechoulam Anandamide, a brain endogenous compound, interacts specifically with cannabinoid receptors and inhibits adenylate cyclase J Neurochem 61 1 1993 352 355
148. K. Wakamatsu, T. Masaki, F. Itoh, K. Kondo, and K. Sudo Isolation of fatty acid amide as an angiogenic principle from bovine mesentery Biochem Biophys Res Commun 168 2 1990 423 429
149. M. Wartmann, D. Campbell, A. Subramanian, S.H. Burstein, and R.J. Davis The MAP kinase signal transduction pathway is activated by the endogenous cannabinoid anandamide FEBS Lett 359 2-3 1995 133 136
150. A. Weber, J. Ni, K.H. Ling, A. Acheampong, D.D. Tang-Liu, and R. Burk Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometry J Lipid Res 45 4 2004 757 763
151. T. Wenger, B.E. Toth, and B.R. Martin Effects of anandamide (endogen cannabinoid) on anterior pituitary hormone secretion in adult ovariectomized rats Life Sci 56 23-24 1995 2057 2063
152. T.M. Westlake, A.C. Howlett, T.I. Bonner, L.A. Matsuda, and M. Herkenham Cannabinoid receptor binding and messenger RNA expression in human brain: an in vitro receptor autoradiography and in situ hybridization histochemistry study of normal aged and Alzheimer's brains Neuroscience 63 3 1994 637 652
153. A.W. Zuardi, I. Shirakawa, E. Finkelfarb, and I.G. Karniol Action of cannabidiol on the anxiety and other effects produced by delta 9-THC in normal subjects Psychopharmacology (Berl) 76 3 1982 245 250
154. P.M. Zygmunt, J. Petersson, D.A. Andersson, H. Chuang, M. Sorgard, and V. Di Marzo Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide Nature 400 6743 1999 452 457
155. P.M. Zygmunt, H. Chuang, P. Movahed, D. Julius, and E.D. Hogestatt The anandamide transport inhibitor AM404 activates vanilloid receptors Eur J Pharmacol 396 1 2000 39 42