Endocannabinoid receptor pharmacology

Current Topics in Behavioral Neurosciences

Volumn 1, Issue , 2009, Pages 37-63

  Yao, Betty ^a   Mackie, Ken ^b  

^a ABBOTT LABORATORIES   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

Allosteric modulator; Efficacy; Potency; Protean agonism; Radioligand binding

Indexed keywords

CANNABINOID RECEPTOR; ENDOCANNABINOID; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); ION CHANNEL;

ANIMAL; CLASSIFICATION; DRUG ANTAGONISM; DRUG EFFECT; DRUG POTENTIATION; GENETICS; HUMAN; METABOLISM; PHYSIOLOGY; PROTEIN BINDING; REVIEW; SIGNAL TRANSDUCTION;

ANIMALS; ENDOCANNABINOIDS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HUMANS; ION CHANNELS; PROTEIN BINDING; RECEPTOR CROSS-TALK; RECEPTORS, CANNABINOID; SIGNAL TRANSDUCTION;

EID: 79952108269     PISSN: 18663370     EISSN: 18663389     Source Type: Book Series    
DOI: 10.1007/978-3-540-88955-7_2     Document Type: Review

References (127)

1. Addy C et al. (2008) The acyclic CB1R inverse agonist taranabant mediates weight loss by increasing energy expenditure and decreasing caloric intake. Cell Metab 7(1):68-78
2. Akopian AN et al. (2008) Cannabinoids desensitize capsaicin and mustard oil responses in sensory neurons via TRPA1 activation. J Neurosci 28(5):1064-1075
3. Anday JK, Mercier RW (2005) Gene ancestry of the cannabinoid receptor family. Pharmacol Res 52(6):463-466
4. Andersson H et al. (2003) Membrane assembly of the cannabinoid receptor 1: impact of a long N-terminal tail. Mol Pharmacol 64(3):570-577
5. Andersson DA, Nash M, Bevan S (2007) Modulation of the cold-activated channel TRPM8 by lysophospholipids and polyunsaturated fatty acids. J Neurosci 27(12):3347-3355
6. Bacci A, Huguenard JR, Prince DA (2004) Long-lasting self-inhibition of neocortical interneurons mediated by endocannabinoids. Nature 431(7006):312-316
7. Baker D et al. (2000) Cannabinoids control spasticity and tremor in a multiple sclerosis model. Nature 404(6773):84-87
8. Barann M et al. (2002) Direct inhibition by cannabinoids of human 5-HT3A receptors: probable involvement of an allosteric modulatory site. Br J Pharmacol 137(5):589-596
9. Begg M et al. (2005) Evidence for novel cannabinoid receptors. Pharmacol Ther 106(2):133-145
10. Benito C et al. (2007) Cannabinoid CB1 and CB2 receptors and fatty acid amide hydrolase are specific markers of plaque cell subtypes in human multiple sclerosis. J Neurosci 27(9):2396-2402
11. Berghuis P et al. (2005) Endocannabinoids regulate interneuron migration and morphogenesis by transactivating the TrkB receptor. Proc Natl Acad Sci USA 102(52):19115-19120
12. Bergman J et al. (2008) Some effects of CB1 antagonists with inverse agonist and neutral biochemical properties. Physiol Behav 93(4-5):666-670
13. Black SC (2004) Cannabinoid receptor antagonists and obesity. Curr Opin Investig Drugs 5(4):389-394
14. Bockaert J, Pin JP (1999) Molecular tinkering of G protein-coupled receptors: an evolutionary success. Embo J 18(7):1723-1729
15. Bond RA, Ijzerman AP (2006) Recent developments in constitutive receptor activity and inverse agonism, and their potential for GPCR drug discovery. Trends Pharmacol Sci 27(2):92-96
16. Bonhaus DW et al. (1998) Dual activation and inhibition of adenylyl cyclase by cannabinoid receptor agonists: evidence for agonist-specific trafficking of intracellular responses. J Pharmacol Exp Ther 287(3):884-888
17. Bouaboula M et al. (1999a) Gi protein modulation induced by a selective inverse agonist for the peripheral cannabinoid receptor CB2: implication for intracellular signalization crossregulation. Mol Pharmacol 55(3):473-480
18. Bouaboula M, Dussossoy D, Casellas P (1999b) Regulation of peripheral cannabinoid receptor CB2 phosphorylation by the inverse agonist SR 144528. Implications for receptor biological responses. J Biol Chem 274(29):20397-20405
19. Bradshaw HB, Walker JM (2005) The expanding field of cannabimimetic and related lipid mediators. Br J Pharmacol 144(4):459-465
20. Breivogel CS et al. (2001) Evidence for a new G protein-coupled cannabinoid receptor in mouse brain. Mol Pharmacol 60(1):155-163
21. Brown SM, Wager-Miller J, Mackie K (2002) Cloning and molecular characterization of the rat CB2 cannabinoid receptor. Biochim Biophys Acta 1576(3):255-264
22. Canals M, Milligan G (2008) Constitutive activity of the cannabinoid CB1 receptor regulates the function of co-expressed Mu opioid receptors. J Biol Chem 283(17):11424-11434
23. Chambers AP et al. (2007) A neutral CB1 receptor antagonist reduces weight gain in rat. Am J Physiol Regul Integr Comp Physiol 293(6):R2185-R2193
24. Compton DR et al. (1992) Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol. J Pharmacol Exp Ther 263(3):1118-1126
25. DevaneWAet al. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258(5090):1946-1949
26. Dziadulewicz EK et al. (2007) Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl) methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration. J Med Chem 50(16):3851-3856
27. Ehlers CL et al. (2007) Association between single nucleotide polymorphisms in the cannabinoid receptor gene (CNR1) and impulsivity in southwest California Indians. Twin Res Hum Genet 10(6):805-811
28. Elphick MR, Egertova M (2005) The phylogenetic distribution and evolutionary origins of endocannabinoid signalling. Handb Exp Pharmacol 168:283-297
29. Fay JF, Dunham TD, Farrens DL (2005) Cysteine residues in the human cannabinoid receptor: only C257 and C264 are required for a functional receptor, and steric bulk at C386 impairs antagonist SR141716A binding. Biochemistry 44(24):8757-8769
30. Felder CC et al. (1993) Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90(16):7656-7660
31. Felder CC et al. (1995) Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol 48(3):443-450
32. Felder CC et al. (1998) LY320135, a novel cannabinoid CB1 receptor antagonist, unmasks coupling of the CB1 receptor to stimulation of cAMP accumulation. J Pharmacol Exp Ther 284(1):291-297
33. Feng W, Song ZH (2003) Effects of D3.49A, R3.50A, and A6.34E mutations on ligand binding and activation of the cannabinoid-2 (CB2) receptor. Biochem Pharmacol 65(7):1077-1085
34. Foloppe N et al. (2008) Discovery of a novel class of selective human CB1 inverse agonists. Bioorg Med Chem Lett 18(3):1199-1206
35. Freund TF, Katona I, Piomelli D (2003) Role of endogenous cannabinoids in synaptic signaling. Physiol Rev 83(3):1017-1066
36. Galandrin S, Oligny-Longpre G, Bouvier M (2007) The evasive nature of drug efficacy: implications for drug discovery. Trends Pharmacol Sci 28(8):423-430
37. Galiegue S et al. (1995) Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem 232(1):54-61
38. Garcia DE et al. (1998) Protein kinase C disrupts cannabinoid actions by phosphorylation of the CB1 cannabinoid receptor. J Neurosci 18(8):2834-2841
39. Gbahou F et al. (2003) Protean agonism at histamine H3 receptors in vitro and in vivo. Proc Natl Acad Sci USA 100(19):11086-11091
40. 35S]Sch225336. J Biol Chem 281 (38):28143-28151
41. Govaerts SJ et al. (2004) Characterization of the pharmacology of imidazolidinedione derivatives at cannabinoid CB1 and CB2 receptors. Eur J Pharmacol 495(1):43-53
42. Griffin G, Tao Q, Abood ME (2000) Cloning and pharmacological characterization of the rat CB2 cannabinoid receptor. J Pharmacol Exp Ther 292(3):886-894
43. Hamdani N et al. (2008) The CNR1 gene as a pharmacogenetic factor for antipsychotics rather than a susceptibility gene for schizophrenia. Eur Neuropsychopharmacol 18(1):34-40
44. Heimann AS et al. (2007) Hemopressin is an inverse agonist of CB1 cannabinoid receptors. Proc Natl Acad Sci USA 104(51):20588-20593
45. HerkenhamMet al. (1991) Characterization and localization of cannabinoid receptors in rat brain: a quantitative in vitro autoradiographic study. J Neurosci 11(2):563-583
46. Ho BY et al. (1999) Coupling of the expressed cannabinoid CB1 and CB2 receptors to phospholipase C and G protein-coupled inwardly rectifying K + channels. Receptor Channel 6(5):363-374
47. Hoenicka J et al. (2007) Association in alcoholic patients between psychopathic traits and the additive effect of allelic forms of the CNR1 and FAAH endocannabinoid genes, and the 3' region of the DRD2 gene. Neurotox Res 11(1):51-60
48. Horswill JG et al. (2007) PSNCBAM-1, a novel allosteric antagonist at cannabinoid CB1 receptors with hypophagic effects in rats. Br J Pharmacol 152(5):805-814
49. Howlett AC (2005) Cannabinoid receptor signaling. Handb Exp Pharmacol 168:53-79
50. Howlett AC et al. (2002) International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol Rev 54(2):161-202
51. Hsieh C et al. (1999) Internalization and recycling of the CB1 cannabinoid receptor. J Neurochem 73(2):493-501
52. Ibrahim MM et al. (2005) CB2 cannabinoid receptor activation produces antinociception by stimulating peripheral release of endogenous opioids. Proc Natl Acad Sci USA 102 (8):3093-3098
53. Jhaveri MD et al. (2008) Evidence for a novel functional role of cannabinoid CB receptors in the thalamus of neuropathic rats. Eur J NeuroSci 27(9):2482
54. Jin W et al. (1999) Distinct domains of the CB1 cannabinoid receptor mediate desensitization and internalization. J Neurosci 19(10):3773-3780
55. Karsak M et al. (2005) Cannabinoid receptor type 2 gene is associated with human osteoporosis. Hum Mol Genet 14(22):3389-3396
56. Kenakin T (2004) Efficacy as a vector: the relative prevalence and paucity of inverse agonism. Mol Pharmacol 65(1):2-11
57. Kreitzer AC, Carter AG, Regehr WG (2002) Inhibition of interneuron firing extends the spread of endocannabinoid signaling in the cerebellum. Neuron 34(5):787-796
58. Lauckner JE, Hille B, Mackie K (2005) The cannabinoid agonist WIN55, 212-2 increases intracellular calcium via CB1 receptor coupling to Gq/11 G proteins. Proc Natl Acad Sci USA 102 (52):19144-19149
59. Lauckner JE et al. (2008) GPR55 is a cannabinoid receptor that increases intracellular calcium and inhibits M current. Proc Natl Acad Sci USA 105(7):2699-2704
60. Lavey BJ et al. (2005) Triaryl bis-sulfones as a new class of cannabinoid CB2 receptor inhibitors: identification of a lead and initial SAR studies. Bioorg Med Chem Lett 15(3):783-786
61. Lin S et al. (1998) Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. J Med Chem 41 (27):5353-5361
62. Luk T et al. (2004) Identification of a potent and highly efficacious, yet slowly desensitizing CB1 cannabinoid receptor agonist. Br J Pharmacol 142(3):495-500
63. Mackie K et al. (1995) 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):6552-6561
64. Maingret F et al. (2001) The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1. Embo J 20(1-2):47-54
65. Marriott KS, Huffman JW (2008) Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor. Curr Top Med Chem 8(3):187-204
66. Martini L et al. (2007) Ligand-induced down-regulation of the cannabinoid 1 receptor is mediated by the G-protein-coupled receptor-associated sorting protein GASP1. Faseb J 21(3):802-811
67. Matsuda LA et al. (1990) Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346(6284):561-564
68. Mauler F et al. (2002) Characterization of the diarylether sulfonylester (-)-(R)-3-(2-hydroxymethylindanyl-4-oxy) phenyl-4, 4, 4-trifluoro-1-sulfonate (BAY 38-7271) as a potent cannabinoid receptor agonist with neuroprotective properties. J Pharmacol Exp Ther 302(1):359-368
69. McAllister SD et al. (2002) A critical role for a tyrosine residue in the cannabinoid receptors for ligand recognition. Biochem Pharmacol 63(12):2121-2136
70. McAllister SD et al. (2003) An aromatic microdomain at the cannabinoid CB(1) receptor constitutes an agonist/inverse agonist binding region. J Med Chem 46(24):5139-5152
71. McPartland JM, Norris RW, Kilpatrick CW (2007) Coevolution between cannabinoid receptors and endocannabinoid ligands. Gene 397(1-2):126-135
72. Morello JP, Bouvier M (1996) Palmitoylation: a post-translational modification that regulates signalling from G-protein coupled receptors. Biochem Cell Biol 74(4):449-457
73. Munro S, Thomas KL, Abu-Shaar M (1993) Molecular characterization of a peripheral receptor for cannabinoid. Nature (London, United Kingdom) 6441:61-65
74. Niehaus JL et al. (2007) CB1 cannabinoid receptor activity is modulated by the cannabinoid receptor interacting protein CRIP 1a. Mol Pharmacol 72(6):1557-1566
75. Nyiri G et al. (2005) CB1 cannabinoid receptors are enriched in the perisynaptic annulus and on preterminal segments of hippocampal GABAergic axons. Neuroscience 136(3):811-822
76. Ohta H et al. (2008) Imine derivatives as new potent and selective CB2 cannabinoid receptor agonists with an analgesic action. Bioorg Med Chem 16(3):1111-1124
77. Oka S et al. (2007) Identification of GPR55 as a lysophosphatidylinositol receptor. Biochem Biophys Res Commun 362(4):928-934
78. Oz M (2006) Receptor-independent actions of cannabinoids on cell membranes: focus on endocannabinoids. Pharmacol Ther 111(1):114-144
79. Oz M et al. (2004) Differential effects of endogenous and synthetic cannabinoids on alpha7-nicotinic acetylcholine receptor-mediated responses in Xenopus Oocytes. J Pharmacol Exp Ther 310(3):1152-1160
80. Palczewski K et al. (2000) Crystal structure of rhodopsin: A G protein-coupled receptor. Science 289(5480):739-745
81. Poling JS et al. (1996) Anandamide, an endogenous cannabinoid, inhibits Shaker-related voltagegated K+ channels. Neuropharmacology 35(7):983-991
82. Portier M et al. (1999) SR 144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist. J Pharmacol Exp Ther 288(2):582-589
83. Price MR et al. (2005) Allosteric modulation of the cannabinoid CB1 receptor. Mol Pharmacol 68(5):1484-1495
84. Pryce G, Baker D (2007) Control of spasticity in a multiple sclerosis model is mediated by CB1, not CB2, cannabinoid receptors. Br J Pharmacol 150(4):519-525
85. Reggio PH (2002) Endocannabinoid structure-activity relationships for interaction at the cannabinoid receptors. Prostaglandins Leukot Essent Fatty Acids 66(2-3):143-160
86. Richardson D et al. (2007) Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry. Anal Biochem 360(2):216-226
87. Rinaldi-Carmona M et al. (1996) Characterization and distribution of binding sites for [3H]-SR 141716A, a selective brain (CB1) cannabinoid receptor antagonist, in rodent brain. Life Sci 58 (15):1239-1247
88. Rinaldi-Carmona M et al. (1998) Modulation of CB1 cannabinoid receptor functions after a longterm exposure to agonist or inverse agonist in the Chinese hamster ovary cell expression system. J Pharmacol Exp Ther 287(3):1038-1047
89. Ross RA (2003) Anandamide and vanilloid TRPV1 receptors. Br J Pharmacol 140(5):790-801
90. Ross RA et al. (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630. Br J Pharmacol 126(3):665-672
91. Ryan WJ et al. (1997) Potent anandamide analogs: the effect of changing the length and branching of the end pentyl chain. J Med Chem 40(22):3617-3625
92. Ryberg E et al. (2005) Identification and characterisation of a novel splice variant of the human CB1 receptor. FEBS Lett 579(1):259-264
93. Ryberg E et al. (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br J Pharmacol 152(7):1092-1101
94. Schonbrunn A (2007) Selective agonism in somatostatin receptor signaling and regulation. Mol Cell Endocrinol 286(1-2):35-39
95. Seifert J et al. (2007) No association of CNR1 gene variations with susceptibility to schizophrenia. Neurosci Lett 426(1):29-33
96. Selinger Z (2008) Discovery of G protein signaling. Annu Rev Biochem 77:1-13
97. Shire D et al. (1995) An amino-terminal variant of the central cannabinoid receptor resulting from alternative splicing. J Biol Chem 270(8):3726-3731
98. Shire D et al. (1996) Structural features of the central cannabinoid CB1 receptor involved in the binding of the specific CB1 antagonist SR 141716A. J Biol Chem 271(12):6941-6946
99. Shire D et al. (1999) Cannabinoid receptor interactions with the antagonists SR 141716A and SR 144528. Life Sci 65(6-7):627-635
100. Shoemaker JL et al. (2005) Agonist-directed trafficking of response by endocannabinoids acting at CB2 receptors. J Pharmacol Exp Ther 315(2):828-838
101. Siegfried Z et al. (2004) Association study of cannabinoid receptor gene (CNR1) alleles and anorexia nervosa: differences between restricting and binging/purging subtypes. Am J Med Genet B Neuropsychiatr Genet 125(1):126-130
102. 35S]thio]-triphosphate binding. Proc Natl Acad Sci USA 92(16):7242-7246
103. Sim LJ et al. (1996) Differences in G-protein activation by mu-and delta-opioid, and cannabinoid, receptors in rat striatum. Eur J Pharmacol 307(1):97-105
104. Sink KS et al. (2008) The novel cannabinoid CB1 receptor neutral antagonist AM4113 suppresses food intake and food-reinforced behavior but does not induce signs of nausea in rats. Neuropsychopharmacology 33(4):946-955
105. Sipe JC et al. (2005) Reduced endocannabinoid immune modulation by a common cannabinoid 2 (CB2) receptor gene polymorphism: possible risk for autoimmune disorders. J Leukoc Biol 78(1):231-238
106. Song ZH, Bonner TI (1996) A lysine residue of the cannabinoid receptor is critical for receptor recognition by several agonists but not WIN55212-2. Mol Pharmacol 49(5):891-896
107. Stella N, Schweitzer P, Piomelli D (1997) A second endogenous cannabinoid that modulates longterm potentiation. Nature 388(6644):773-778
108. Sugiura T et al. (1995) 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem Biophys Res Commun 215(1):89-97
109. Sun Y, McGarrigle D, Huang XY (2007) When a G protein-coupled receptor does not couple to a G protein. Mol Biosyst 3(12):849-854
110. Tao Q, Abood ME (1998) Mutation of a highly conserved aspartate residue in the second transmembrane domain of the cannabinoid receptors, CB1 and CB2, disrupts G-protein coupling. J Pharmacol Exp Ther 285(2):651-658
111. Thomas BF et al. (1998) Comparative receptor binding analyses of cannabinoid agonists and antagonists. J Pharmacol Exp Ther 285(1):285-292
112. Tian X et al. (2005) The conformation, location, and dynamic properties of the endocannabinoid ligand anandamide in a membrane bilayer. J Biol Chem 280(33):29788-29795
113. Ueda Y et al. (2005) Involvement of cannabinoid CB(2) receptor-mediated response and efficacy of cannabinoid CB(2) receptor inverse agonist, JTE-907, in cutaneous inflammation in mice. Eur J Pharmacol 520(1-3):164-171
114. Ujike H et al. (2002) CNR1, central cannabinoid receptor gene, associated with susceptibility to hebephrenic schizophrenia. Mol Psychiatry 7(5):515-518
115. Urban JD et al. (2007) Functional selectivity and classical concepts of quantitative pharmacology. J Pharmacol Exp Ther 320(1):1-13
116. Valk PJ et al. (1997) The genes encoding the peripheral cannabinoid receptor and alpha-Lfucosidase are located near a newly identified common virus integration site, Evi11. J Virol 71(9):6796-6804
117. Van Sickle MD et al. (2005) Identification and functional characterization of brainstem cannabinoid CB2 receptors. Science 310(5746):329-332
118. Vasquez C, Lewis DL (1999) The CB1 cannabinoid receptor can sequester G-proteins, making them unavailable to couple to other receptors. J Neurosci 19(21):9271-9280
119. Waldeck-Weiermair M et al. (2008) Integrin clustering enables anandamide-induced Ca2+ signaling in endothelial cells via GPR55 by protection against CB1-receptor-triggered repression. J Cell Sci 121:1704-1717
120. Whiteside GT et al. (2005) A role for cannabinoid receptors, but not endogenous opioids, in the antinociceptive activity of the CB2-selective agonist, GW405833. Eur J Pharmacol 528(1-3):65-72
121. Wotherspoon G et al. (2005) Peripheral nerve injury induces cannabinoid receptor 2 protein expression in rat sensory neurons. Neuroscience 135(1):235-245
122. Wright KL, Duncan M, Sharkey KA (2008) Cannabinoid CB2 receptors in the gastrointestinal tract: a regulatory system in states of inflammation. Br J Pharmacol 153(2):263-270
123. Yao BB et al. (2006) In vitro pharmacological characterization of AM1241: a protean agonist at the cannabinoid CB2 receptor? Br J Pharmacol 149(2):145-154
124. Yao BB et al. (2008) In vitro and in vivo characterization of A-796260: a selective cannabinoid CB2 receptor agonist exhibiting analgesic activity in rodent pain models. Br J Pharmacol 153(2):390-401
125. Yao BB et al. (2009) Characterization of a cannabinoid CB2 receptor-selective agonist, A-836339 [2,2,3,3-tetramethyl-cyclopropanecarboxylic acid [3-(2-Methoxy-ethyl)-4,5-dimethyl-3Hthiazol-(2Z)-ylidene]-amide], using in vitro pharmacological assays, in vivo pain models, and pharmacological magnetic resonance imaging. J Pharmacol Exp Ther 328(1):141-151
126. Zhang J et al. (2003) Induction of CB2 receptor expression in the rat spinal cord of neuropathic but not inflammatory chronic pain models. Eur J Neurosci 17(12):2750-2754
127. Zuo L et al. (2007) CNR1 variation modulates risk for drug and alcohol dependence. Biol Psychiatry 62(6):616-626