Interaction of endocannabinoid receptors with biological membranes

Current Medicinal Chemistry

Volumn 17, Issue 14, 2010, Pages 1487-1499

  Dainese, E ^a   Oddi, S ^a,b   Maccarrone, M ^a,b  

^a UNIVERSITY OF TERAMO   (Italy)

^b IRCCS FONDAZIONE SANTA LUCIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 ARACHIDONOYLGLYCEROL; ANANDAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CHOLESTEROL; ENDOCANNABINOID; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR; VANILLOID RECEPTOR; VANILLOID RECEPTOR 1; VANILLOID RECEPTOR 4;

CAVEOLA; CHANNEL GATING; DIFFUSION; HUMAN; LIGAND BINDING; LIPID BILAYER; LIPID RAFT; MEMBRANE BINDING; MOLECULAR DYNAMICS; NONHUMAN; RECEPTOR BINDING; REVIEW; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

CHOLESTEROL; ENDOCANNABINOIDS; LIPID BILAYERS; PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS; RECEPTORS, CANNABINOID; SIGNAL TRANSDUCTION; TRPV CATION CHANNELS;

EID: 77950632004     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986710790980087     Document Type: Review

References (122)

1. Di Marzo, V. Targeting the endocannabinoid system: to enhance or reduce? Nat. Rev. Drug Discov., 2008, 7(5), 438-455. (Pubitemid 351649182)
2. Matsuda, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. I. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature, 1990, 346(6284), 561-564. (Pubitemid 20238806)
3. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Molecular characterization of a peripheral receptor for cannabinoids. Nature, 1993, 365(6441), 61-65. (Pubitemid 23305569)
4. Starowicz, K.; Nigam, S.; Di Marzo, V. Biochemistry and pharmacology of endovanilloids. Pharmacol. Ther., 2007, 114(1), 13-33.
5. Nilius, B.; Vriens, J.; Prenen, J.; Droogmans, G.; Voets, T. TRPV4 calcium entry channel: a paradigm for gating diversity. Am. J. Physiol. Cell Physiol., 2004, 286(2), C195-C205.
6. Rockwell, C. E.; Snider, N. T.; Thompson, J. T.; Vanden Heuvel, J. P.; Kaminski, N. E. Interleukin-2 suppression by 2-arachidonyl glycerol is mediated through peroxisome proliferator-activated receptor gamma independently of cannabinoid receptors 1 and 2. Mol. Pharmacol., 2006, 70(1), 101-111. (Pubitemid 43920800)
7. Ghosh, M.; Wang, H.; Ai, Y.; Romeo, E.; Luyendyk, J. P.; Peters, J. M.; Mackman, N.; Dey, S. K.; Hla, T. COX-2 suppresses tissue factor expression via endocannabinoid-directed PPARdelta activation. J. Exp. Med., 2007, 204(9), 2053-2061. (Pubitemid 47360868)
8. Jhaveri, M. D.; Richardson, D.; Robinson, I.; Garle, M. J.; Patel, A.; Sun, Y.; Sagar, D. R.; Bennett, A. J.; Alexander, S. P.; Kendall, D. A.; Barrett, D. A.; Chapman, V. 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.
9. Lauckner, J. E.; Jensen, J. B.; Chen, H. Y.; Lu, H. C.; Hille, B.; Mackie, K. GPR55 is a cannabinoid receptor that increases intracellular calcium and inhibits M current. Proc. Natl. Acad. Sci. USA, 2008, 105(7), 2699-2704. (Pubitemid 351520576)
10. Brown, A. J.; Robin, H. C. Is GPR55 an anandamide receptor? Vitam. Horm., 2009, 81 111-137.
11. Giuffrida, A.; Rodriguez, d. F.; Nava, F.; Loubet-Lescoulie, P.; Piomelli, D. Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404. Eur. J. Pharmacol., 2000, 408(2), 161-168.
12. Oddi, S.; Fezza, F.; Pasquariello, N.; D'Agostino, A.; Catanzaro, G.; De Simone, C.; Rapino, C.; Finazzi-Agrò, A.; Maccarrone, M. Molecular identification of albumin and Hsp70 as cytosolic anandamide-binding proteins. Chem. Biol., 2009, 16(6), 624-632.
13. Kaczocha, M.; Glaser, S. T.; Deutsch, D. G. Identification of intracellular carriers for the endocannabinoid anandamide. Proc. Natl. Acad. Sci. USA, 2009, 106(15), 6375-6380.
14. Singer, S. J.; Nicolson, G. L. The fluid mosaic model of the structure of cell membranes. Science, 1972, 175(23), 720-731.
15. Lindahl, E.; Sansom, M. S. Membrane proteins: molecular dynamics simulations. Curr. Opin. Struct. Biol., 2008, 18(4), 425-431.
16. Forneris, F.; Mattevi, A. Enzymes without borders: mobilizing substrates, delivering products. Science, 2008, 321(5886), 213-216. (Pubitemid 351989085)
17. Brown, D. A.; London, E. Functions of lipid rafts in biological membranes. Annu. Rev. Cell Dev. Biol., 1998, 14 111-136. (Pubitemid 29001451)
18. Galbiati, F.; Razani, B.; Lisanti, M. P. Emerging themes in lipid rafts and caveolae. Cell, 2001, 106(4), 403-411.
19. Simons, K.; Toomre, D. Lipid rafts and signal transduction. Nat. Rev. Mol. Cell Biol., 2000, 1(1), 31-39.
20. Pike, L. J. Growth factor receptors, lipid rafts and caveolae: an evolving story. Biochim. Biophys. Acta, 2005, 1746(3), 260-273.
21. Pike, L. J. Lipid rafts: bringing order to chaos. J. Lipid Res., 2003, 44(4), 655-667.
22. Dainese, E.; Oddi, S.; Bari, M.; Maccarrone, M. Modulation of the endocannabinoid system by lipid rafts. Curr. Med. Chem., 2007, 14(25), 2702-2715. (Pubitemid 350048324)
23. Lingwood, D.; Ries, J.; Schwille, P.; Simons, K. Plasma membranes are poised for activation of raft phase coalescence at physiological temperature. Proc. Natl. Acad. Sci. USA, 2008, 105(29), 10005-10010.
24. Simons, K.; Ikonen, E. Functional rafts in cell membranes. Nature, 1997, 387(6633), 569-572.
25. Meder, D.; Simons, K. Lipid Rafts and Caveolae: From Membrane Biophysics to Cell Biology, Fielding, C. J., Ed. Wiley, New York: 2006; pp. 1-23.
26. Xu, X.; London, E. The effect of sterol structure on membrane lipid domains reveals how cholesterol can induce lipid domain formation. Biochemistry, 2000, 39(5), 843-849. (Pubitemid 30075310)
27. Ostermeyer, A. G.; Beckrich, B. T.; Ivarson, K. A.; Grove, K. E.; Brown, D. A. Glycosphingolipids are not essential for formation of detergent-resistant membrane rafts in melanoma cells. methyl-beta-cyclodextrin does not affect cell surface transport of a GPI-anchored protein. J. Biol. Chem., 1999, 274(48), 34459-34466.
28. Ge, M.; Field, K. A.; Aneja, R.; Holowka, D.; Baird, B.; Freed, J. H. Electron spin resonance characterization of liquid ordered phase of detergent-resistant membranes from RBL-2H3 cells. Biophys. J., 1999, 77(2), 925-933.
29. Baumgart, T.; Das, S.; Webb, W. W.; Jenkins, J. T. Membrane elasticity in giant vesicles with fluid phase coexistence. Biophys. J., 2005, 89(2), 1067-1080.
30. Hansen, G. H.; Niels-Christiansen, L. L.; Thorsen, E.; Immerdal, L.; Danielsen, E. M. Cholesterol depletion of enterocytes. Effect on the Golgi complex and apical membrane trafficking. J. Biol. Chem., 2000, 275(7), 5136-5142.
31. Bari, M.; Battista, N.; Fezza, F.; Finazzi-Agrò, A.; Maccarrone, M. Lipid rafts control signaling of type-1 cannabinoid receptors in neuronal cells. Implications for anandamide-induced apoptosis. J. Biol. Chem., 2005, 280(13), 12212-12220. (Pubitemid 40491032)
32. Bennett, W. F.; MacCallum, J. L.; Hinner, M. J.; Marrink, S. J.; Tieleman, D. P. Molecular view of cholesterol flip-flop and chemical potential in different membrane environments. J. Am. Chem. Soc., 2009, 131(35), 12714-12720.
33. Lange, Y.; Ye, J.; Duban, M. E.; Steck, T. L. Activation of membrane cholesterol by 63 amphipaths. Biochemistry, 2009, 48(36), 8505-8515.
34. Devaux, P. F.; Morris, R. Transmembrane asymmetry and lateral domains in biological membranes. Traffic, 2004, 5(4), 241-246. (Pubitemid 38455747)
35. Hage Chahine, J. M.; Cribier, S.; Devaux, P. F. Phospholipid transmembrane domains and lateral diffusion in fibroblasts. Proc. Natl. Acad. Sci. USA, 1993, 90(2), 447-451. (Pubitemid 23028880)
36. Julien, M.; Tournier, J. F.; Tocanne, J. F. Differences in the transbilayer and lateral motions of fluorescent analogs of phosphatidylcholine and phosphatidylethanolamine in the apical plasma membrane of bovine aortic endothelial cells. Exp. Cell Res., 1993, 208(2), 387-397.
37. Wisniewska, A.; Draus, J.; Subczynski, W. K. Is a fluid-mosaic model of biological membranes fully relevant? Studies on lipid organization in model and biological membranes. Cell Mol. Biol. Lett., 2003, 8(1), 147-159.
38. Subczynski, W. K.; Kusumi, A. Dynamics of raft molecules in the cell and artificial membranes: approaches by pulse EPR spin labeling and single molecule optical microscopy. Biochim. Biophys. Acta, 2003, 1610(2), 231-243. (Pubitemid 36324467)
39. Aussenac, F.; Tavares, M.; Dufourc, E. J. Cholesterol dynamics in membranes of raft composition: a molecular point of view from 2H and 31P solid-state NMR. Biochemistry, 2003, 42(6), 1383-1390.
40. Chen, X.; Jayne, L. M.; Barlow, D. J.; Morris, R. J.; Heenan, R. K.; Quinn, P. J. The structure of detergent-resistant membrane vesicles from rat brain cells. Biochim. Biophys. Acta, 2009, 1788(2), 477-483.
41. Hildebrand, P. W.; Preissner, R.; Frommel, C. Structural features of transmembrane helices. FEBS Lett., 2004, 559(1-3), 145-151.
42. Mayor, S.; Rao, M. Rafts: scale-dependent, active lipid organization at the cell surface. Traffic, 2004, 5(4), 231-240. (Pubitemid 38455746)
43. Biswas, K. K.; Sarker, K. P.; Abeyama, K.; Kawahara, K.; Iino, S.; Otsubo, Y.; Saigo, K.; Izumi, H.; Hashiguchi, T.; Yamakuchi, M.; Yamaji, K.; Endo, R.; Suzuki, K.; Imaizumi, H.; Maruyama, I. Membrane cholesterol but not putative receptors mediates anandamide-induced hepatocyte apoptosis. Hepatology, 2003, 38(5), 1167-1177. (Pubitemid 37314825)
44. Di Pasquale, E.; Chahinian, H.; Sanchez, P.; Fantini, J. The insertion and transport of anandamide in synthetic lipid membranes are both cholesterol-dependent. PLoS. ONE, 2009, 4(3), e4989.
45. Garmy, N.; Taieb, N.; Yahi, N.; Fantini, J. Interaction of cholesterol with sphingosine: physicochemical characterization and impact on intestinal absorption. J. Lipid Res., 2005, 46(1), 36-45. (Pubitemid 40066669)
46. Rimmerman, N.; Hughes, H. V.; Bradshaw, H. B.; Pazos, M. X.; Mackie, K.; Prieto, A. L.; Walker, J. M. Compartmentalization of endocannabinoids into lipid rafts in a dorsal root ganglion cell line. Br. J. Pharmacol., 2008, 153(2), 380-389.
47. Dainese, E.; Gasperi, V.; Maccarrone, M. Partial QSAR analysis of some selected natural inhibitors of FAAH suggests a working hypothesis for the development of endocannabinoid-based drugs. Curr. Drug Targets. CNS. Neurol. Disord., 2005, 4(6), 709-714. (Pubitemid 41782632)
48. Barnett-Norris, J.; Hurst, D. P.; Lynch, D. L.; Guarnieri, F.; Makriyannis, A.; Reggio, P. H. Conformational memories and the endocannabinoid binding site at the cannabinoid CB1 receptor. J. Med. Chem., 2002, 45(17), 3649-3659.
49. Molcanov, K.; Kojic-Prodic, B.; Raos, N. Analysis of the less common hydrogen bonds involving ester oxygen sp3 atoms as acceptors in the crystal structures of small organic molecules. Acta Crystallogr. B, 2004, 60(Pt 4), 424-432. (Pubitemid 41672902)
50. Sugiura, T.; Kodaka, T.; Nakane, S.; Miyashita, T.; Kondo, S.; Suhara, Y.; Takayama, H.; Waku, K.; Seki, C.; Baba, N.; Ishima, Y. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J. Biol. Chem., 1999, 274(5), 2794-2801. (Pubitemid 29075361)
51. Tian, X.; Guo, J.; Yao, F.; Yang, D. P.; Makriyannis, A. The conformation, location, and dynamic properties of the endocannabinoid ligand anandamide in a membrane bilayer. J. Biol. Chem., 2005, 280(33), 29788-29795. (Pubitemid 41177056)
52. Howlett, A. C.; Barth, F.; Bonner, T. I.; Cabral, G.; Casellas, P.; Devane, W. A.; Felder, C. C.; Herkenham, M.; Mackie, K.; Martin, B. R.; Mechoulam, R.; Pertwee, R. G. International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol. Rev., 2002, 54(2), 161-202.
53. Diaz-Laviada, I.; Ruiz-Llorente, L. Signal transduction activated by cannabinoid receptors. Mini. Rev. Med. Chem., 2005, 5(7), 619-630. (Pubitemid 40933033)
54. Guzman, M. Cannabinoids: potential anticancer agents. Nat. Rev. Cancer, 2003, 3(10), 745-755.
55. Pertwee, R. G. Pharmacology of cannabinoid CB1 and CB2 receptors. Pharmacol. Ther., 1997, 74(2), 129-180.
56. Felder, C. C.; Joyce, K. E.; Briley, E. M.; Mansouri, J.; Mackie, K.; Blond, O.; Lai, Y.; Ma, A. L.; Mitchell, R. L. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol. Pharmacol., 1995, 48(3), 443-450.
57. Lauckner, J. E.; Hille, B.; Mackie, K. The cannabinoid agonist WIN55,212-2 increases intracellular calcium via CB1 receptor coupling to Gq/11 G proteins. Proc. Natl. Acad. Sci. USA, 2005, 102(52), 19144-19149. (Pubitemid 43049580)
58. Bonhaus, D. W.; Chang, L. K.; Kwan, J.; Martin, G. R. Dual activation and inhibition of adenylyl cyclase by cannabinoid receptor agonists: evidence for agonist-specific trafficking of intracellular responses. J. Pharmacol. Exp. Ther., 1998, 287(3), 884-888.
59. Mukhopadhyay, S.; Cowsik, S. M.; Lynn, A. M.; Welsh, W. J.; Howlett, A. C. Regulation of Gi by the CB1 cannabinoid receptor C-terminal juxtamembrane region: structural requirements determined by peptide analysis. Biochemistry, 1999, 38(11), 3447-3455. (Pubitemid 129501409)
60. Howlett, A. C.; Mukhopadhyay, S. Cellular signal transduction by anandamide and 2-arachidonoylglycerol. Chem. Phys. Lipids, 2000, 108(1-2), 53-70.
61. Mukhopadhyay, S.; Howlett, A. C. CB1 receptor-G protein association. Subtype selectivity is determined by distinct intracellular domains. Eur. J. Biochem., 2001, 268(3), 499-505.
62. Xie, X. Q.; Chen, J. Z. NMR structural comparison of the cytoplasmic juxtamembrane domains of G-protein-coupled CB1 and CB2 receptors in membrane mimetic dodecylphosphocholine micelles. J. Biol. Chem., 2005, 280(5), 3605-3612.
63. Mackie, K. Cannabinoid receptor homo- and heterodimerization. Life Sci., 2005, 77(14), 1667-1673.
64. Wager-Miller, J.; Westenbroek, R.; Mackie, K. Dimerization of G protein-coupled receptors: CB1 cannabinoid receptors as an example. Chem. Phys. Lipids, 2002, 121(1-2), 83-89. (Pubitemid 36044545)
65. Kearn, C. S.; Blake-Palmer, K.; Daniel, E.; Mackie, K.; Glass, M. Concurrent stimulation of cannabinoid CB1 and dopamine D2 receptors enhances heterodimer formation: a mechanism for receptor cross-talk? Mol. Pharmacol., 2005, 67(5), 1697-1704. (Pubitemid 40594170)
66. Rios, C.; Gomes, I.; Devi, L. A. mu opioid and CB1 cannabinoid receptor interactions: reciprocal inhibition of receptor signaling and neuritogenesis. Br. J. Pharmacol., 2006, 148(4), 387-395. (Pubitemid 43882074)
67. Hojo, M.; Sudo, Y.; Ando, Y.; Minami, K.; Takada, M.; Matsubara, T.; Kanaide, M.; Taniyama, K.; Sumikawa, K.; Uezono, Y. mu-Opioid receptor forms a functional heterodimer with cannabinoid CB1 receptor: electrophysiological and FRET assay analysis. J. Pharmacol. Sci., 2008, 108(3), 308-319.
68. Sarnataro, D.; Grimaldi, C.; Pisanti, S.; Gazzerro, P.; Laezza, C.; Zurzolo, C.; Bifulco, M. Plasma membrane and lysosomal localization of CB1 cannabinoid receptor are dependent on lipid rafts and regulated by anandamide in human breast cancer cells. FEBS Lett., 2005, 579(28), 6343-6349. (Pubitemid 41612150)
69. Cortright, D. N.; Szallasi, A. Biochemical pharmacology of the vanilloid receptor TRPV1. An update. Eur. J. Biochem., 2004, 271(10), 1814-1819. (Pubitemid 38657335)
70. 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. (Pubitemid 41073659)
71. De Petrocellis, L.; Vellani, V.; Schiano-Moriello, A.; Marini, P.; Magherini, P. C.; Orlando, P.; Di Marzo, V., V Plant-derived cannabinoids modulate the activity of transient receptor potential channels of ankyrin type-1 and melastatin type-8. J. Pharmacol. Exp. Ther., 2008, 325(3), 1007-1015. (Pubitemid 351724325)
72. Fajas, L.; Debril, M. B.; Auwerx, J. Peroxisome proliferator-activated receptor-gamma: from adipogenesis to carcinogenesis. J. Mol. Endocrinol., 2001, 27(1), 1-9. (Pubitemid 32771453)
73. Kostadinova, R.; Wahli, W.; Michalik, L. PPARs in diseases: control mechanisms of inflammation. Curr. Med. Chem., 2005, 12(25), 2995-3009. (Pubitemid 41672488)
74. Sun, Y.; Alexander, S. P.; Garle, M. J.; Gibson, C. L.; Hewitt, K.; Murphy, S. P.; Kendall, D. A.; Bennett, A. J. Cannabinoid activation of PPAR alpha; a novel neuroprotective mechanism. Br. J. Pharmacol., 2007, 152(5), 734-743.
75. Bouaboula, M.; Hilairet, S.; Marchand, J.; Fajas, L.; Le Fur, G.; Casellas, P. Anandamide induced PPARgamma transcriptional activation and 3T3-L1 preadipocyte differentiation. Eur. J. Pharmacol., 2005, 517(3), 174-181. (Pubitemid 40977892)
76. Gasperi, V.; Fezza, F.; Pasquariello, N.; Bari, M.; Oddi, S.; Agrò, A. F.; Maccarrone, M. Endocannabinoids in adipocytes during differentiation and their role in glucose uptake. Cell Mol. Life Sci., 2007, 64(2), 219-229. (Pubitemid 46155701)
77. Rockwell, C. E.; Kaminski, N. E. A cyclooxygenase metabolite of anandamide causes inhibition of interleukin-2 secretion in murine splenocytes. J. Pharmacol. Exp. Ther., 2004, 311(2), 683-690.
78. Bari, M.; Paradisi, A.; Pasquariello, N.; Maccarrone, M. Cholesterol-dependent modulation of type 1 cannabinoid receptors in nerve cells. J. Neurosci. Res., 2005, 81(2), 275-283. (Pubitemid 41153342)
79. Bari, M.; Spagnuolo, P.; Fezza, F.; Oddi, S.; Pasquariello, N.; Finazzi-Agrò, A.; Maccarrone, M. Effect of lipid rafts on Cb2 receptor signaling and 2-arachidonoyl-glycerol metabolism in human immune cells. J. Immunol., 2006, 177(8), 4971-4980. (Pubitemid 44527566)
80. Fonseca, B. M.; Correia-da-Silva, G.; Teixeira, N. A. Anandamide-induced cell death: dual effects in primary rat decidual cell cultures. Placenta, 2009, 30(8), 686-692.
81. Sarnataro, D.; Pisanti, S.; Santoro, A.; Gazzerro, P.; Malfitano, A. M.; Laezza, C.; Bifulco, M. The cannabinoid CB1 receptor antagonist rimonabant (SR141716) inhibits human breast cancer cell proliferation through a lipid raft-mediated mechanism. Mol. Pharmacol., 2006, 70(4), 1298-1306. (Pubitemid 44435982)
82. Maccarrone, M.; De, C., V; Gasperi, V.; Viscomi, M. T.; Rossi, S.; Oddi, S.; Molinari, M.; Musella, A.; Finazzi-Agrò, A.; Centonze, D. Lipid rafts regulate 2-arachidonoylglycerol metabolism and physiological activity in the striatum. J. Neurochem., 2009, 109(2), 371-381.
83. Xu, W.; Yoon, S. I.; Huang, P.; Wang, Y.; Chen, C.; Chong, P. L.; Liu-Chen, L. Y. Localization of the kappa opioid receptor in lipid rafts. J. Pharmacol. Exp. Ther., 2006, 317(3), 1295-1306. (Pubitemid 43764136)
84. Rybin, V. O.; Xu, X.; Lisanti, M. P.; Steinberg, S. F. Differential targeting of beta -adrenergic receptor subtypes and adenylyl cyclase to cardiomyocyte caveolae. A mechanism to functionally regulate the cAMP signaling pathway. J. Biol. Chem., 2000, 275(52), 41447-41457.
85. Xiang, Y.; Rybin, V. O.; Steinberg, S. F.; Kobilka, B. Caveolar localization dictates physiologic signaling of beta 2-adrenoceptors in neonatal cardiac myocytes. J. Biol. Chem., 2002, 277(37), 34280-34286.
86. Wu, D. F.; Yang, L. Q.; Goschke, A.; Stumm, R.; Brandenburg, L. O.; Liang, Y. J.; Hollt, V.; Koch, T. Role of receptor internalization in the agonist-induced desensitization of cannabinoid type 1 receptors. J. Neurochem., 2008, 104(4), 1132-1143. (Pubitemid 351143650)
87. Leterrier, C.; Bonnard, D.; Carrel, D.; Rossier, J.; Lenkei, Z. Constitutive endocytic cycle of the CB1 cannabinoid receptor. J. Biol. Chem., 2004, 279(34), 36013-36021. (Pubitemid 39100609)
88. Leterrier, C.; Laine, J.; Darmon, M.; Boudin, H.; Rossier, J.; Lenkei, Z. Constitutive activation drives compartment-selective endocytosis and axonal targeting of type 1 cannabinoid receptors. J. Neurosci., 2006, 26(12), 3141-3153.
89. Burgermeister, E.; Tencer, L.; Liscovitch, M. Peroxisome proliferator-activated receptor-gamma upregulates caveolin-1 and caveolin-2 expression in human carcinoma cells. Oncogene, 2003, 22(25), 3888-3900. (Pubitemid 36819662)
90. Liu, B.; Hui, K.; Qin, F. Thermodynamics of heat activation of single capsaicin ion channels VR1. Biophys. J., 2003, 85(5), 2988-3006. (Pubitemid 37345788)
91. Liu, M.; Huang, W.; Wu, D.; Priestley, J. V. TRPV1, but not P2X, requires cholesterol for its function and membrane expression in rat nociceptors. Eur. J. Neurosci., 2006, 24(1), 1-6.
92. Fastenberg, M. E.; Shogomori, H.; Xu, X.; Brown, D. A.; London, E. Exclusion of a transmembrane-type peptide from ordered-lipid domains (rafts) detected by fluorescence quenching: extension of quenching analysis to account for the effects of domain size and domain boundaries. Biochemistry, 2003, 42(42), 12376-12390. (Pubitemid 37296514)
93. De Planque, M. R.; Killian, J. A. Protein-lipid interactions studied with designed transmembrane peptides: role of hydrophobic matching and interfacial anchoring. Mol. Membr. Biol., 2003, 20(4), 271-284. (Pubitemid 37406619)
94. Melkonian, K. A.; Ostermeyer, A. G.; Chen, J. Z.; Roth, M. G.; Brown, D. A. Role of lipid modifications in targeting proteins to detergent-resistant membrane rafts. Many raft proteins are acylated, while few are prenylated. J. Biol. Chem., 1999, 274(6), 3910-3917.
95. Shrimpton, C. N.; Borthakur, G.; Larrucea, S.; Cruz, M. A.; Dong, J. F.; Lopez, J. A. Localization of the adhesion receptor glycoprotein Ib-IX-V complex to lipid rafts is required for platelet adhesion and activation. J. Exp. Med., 2002, 196(8), 1057-1066.
96. Shogomori, H.; Hammond, A. T.; Ostermeyer-Fay, A. G.; Barr, D. J.; Feigenson, G. W.; London, E.; Brown, D. A. Palmitoylation and intracellular domain interactions both contribute to raft targeting of linker for activation of T cells. J. Biol. Chem., 2005, 280(19), 18931-18942.
97. Marino, M.; Ascenzi, P. Membrane association of estrogen receptor alpha and beta influences 17beta-estradiol-mediated cancer cell proliferation. Steroids, 2008, 73(9-10), 853-858.
98. Dainese, E.; Oddi, S.; Maccarrone, M. Lipid-mediated dimerization of beta2-adrenergic receptor reveals important clues for cannabinoid receptors. Cell Mol. Life Sci., 2008, 65(15), 2277-2279.
99. Cherezov, V.; Rosenbaum, D. M.; Hanson, M. A.; Rasmussen, S. G.; Thian, F. S.; Kobilka, T. S.; Choi, H. J.; Kuhn, P.; Weis, W. I.; Kobilka, B. K.; Stevens, R. C. High-resolution crystal structure of an engineered human beta2-adrenergic G protein-coupled receptor. Science, 2007, 318(5854), 1258-1265. (Pubitemid 350172884)
100. Karnik, S. S.; Ridge, K. D.; Bhattacharya, S.; Khorana, H. G. Palmitoylation of bovine opsin and its cysteine mutants in COS cells. Proc. Natl. Acad. Sci. USA, 1993, 90(1), 40-44.
101. Smotrys, J. E.; Linder, M. E. Palmitoylation of intracellular signaling proteins: regulation and function. Annu. Rev. Biochem., 2004, 73 559-587. (Pubitemid 39050380)
102. Savi, P.; Zachayus, J. L.; Delesque-Touchard, N.; Labouret, C.; Herve, C.; Uzabiaga, M. F.; Pereillo, J. M.; Culouscou, J. M.; Bono, F.; Ferrara, P.; Herbert, J. M. The active metabolite of Clopidogrel disrupts P2Y12 receptor oligomers and partitions them out of lipid rafts. Proc. Natl. Acad. Sci. USA, 2006, 103(29), 11069-11074.
103. Latif, R.; Ando, T.; Davies, T. F. Lipid rafts are triage centers for multimeric and monomeric thyrotropin receptor regulation. Endocrinology, 2007, 148(7), 3164-3175.
104. Bari, M.; Oddi, S.; De Simone, C.; Spagnolo, P.; Gasperi, V.; Battista, N.; Centonze, D.; Maccarrone, M. Type-1 cannabinoid receptors colocalize with caveolin-1 in neuronal cells. Neuropharmacology, 2008, 54(1), 45-50. (Pubitemid 350299413)
105. Soubias, O.; Niu, S. L.; Mitchell, D. C.; Gawrisch, K. Lipid-rhodopsin hydrophobic mismatch alters rhodopsin helical content. J. Am. Chem. Soc., 2008, 130(37), 12465-12471.
106. Tiburu, E. K.; Bowman, A. L.; Struppe, J. O.; Janero, D. R.; Avraham, H. K.; Makriyannis, A. Solid-state NMR and molecular dynamics characterization of cannabinoid receptor-1 (CB1) helix 7 conformational plasticity in model membranes. Biochim. Biophys. Acta, 2009, 1788(5), 1159-1167.
107. Tiburu, E. K.; Gulla, S. V.; Tiburu, M.; Janero, D. R.; Budil, D. E.; Makriyannis, A. Dynamic conformational responses of a human cannabinoid receptor-1 helix domain to its membrane environment. Biochemistry, 2009, 48(22), 4895-4904.
108. Barnett-Norris, J.; Guarnieri, F.; Hurst, D. P.; Reggio, P. H. Exploration of biologically relevant conformations of anandamide, 2-arachidonylglycerol, and their analogues using conformational memories. J. Med. Chem., 1998, 41(24), 4861-4872.
109. McAllister, S. D.; Rizvi, G.; Anavi-Goffer, S.; Hurst, D. P.; Barnett-Norris, J.; Lynch, D. L.; Reggio, P. H.; Abood, M. E. An aromatic microdomain at the cannabinoid CB(1) receptor constitutes an agonist/inverse agonist binding region. J. Med. Chem., 2003, 46(24), 5139-5152.
110. Durdagi, S.; Papadopoulos, M. G.; Zoumpoulakis, P. G.; Koukoulitsa, C.; Mavromoustakos, T. A computational study on cannabinoid receptors and potent bioactive cannabinoid ligands: homology modeling, docking, de novo drug design and molecular dynamics analysis. Mol. Divers. 2009, [Epub ahead of print].
111. Tuccinardi, T.; Ferrarini, P. L.; Manera, C.; Ortore, G.; Saccomanni, G.; Martinelli, A. Cannabinoid CB2/CB1 selectivity. Receptor modeling and automated docking analysis. J. Med. Chem., 2006, 49, 984-994. (Pubitemid 43221646)
112. Showalter, V. M.; Compton, D. R.; Martin, B. R.; Abood, M. E. Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. J. Pharmacol. Exp. Ther., 1996, 278(3), 989-999.
113. Hermann, A.; Kaczocha, M.; Deutsch, D. G. 2-Arachidonoylglycerol (2-AG) membrane transport: history and outlook. AAPS J., 2006, 8(2), E409-E412.
114. Ashton, J. C.; Wright, J. L.; McPartland, J. M.; Tyndall, J. D. Cannabinoid CB1 and CB2 receptor ligand specificity and the development of CB2-selective agonists. Curr. Med. Chem., 2008, 15(14), 1428-1443.
115. Jordt, S. E.; Julius, D. Molecular basis for species-specific sensitivity to "hot" chili peppers. Cell 2002, 108(3), 421-430.
116. Moiseenkova-Bell, V. Y.; Stanciu, L. A.; Serysheva, I. I.; Tobe, B. J.; Wensel, T. G. Structure of TRPV1 channel revealed by electron cryomicroscopy. Proc. Natl. Acad. Sci. USA, 2008, 105(21), 7451-7455.
117. Brownlow, S. L.; Sage, S. O. Transient receptor potential protein subunit assembly and membrane distribution in human platelets. Thromb. Haemost., 2005, 94(4), 839-845.
118. Hsieh, C.; Brown, S.; Derleth, C.; Mackie, K. Internalization and recycling of the CB1 cannabinoid receptor. J. Neurochem., 1999, 73(2), 493-501.
119. Keren, O.; Sarne, Y. Multiple mechanisms of CB1 cannabinoid receptors regulation. Brain Res., 2003, 980(2), 197-205. (Pubitemid 36829439)
120. Falck, E.; Rog, T.; Karttunen, M.; Vattulainen, I. Lateral diffusion in lipid membranes through collective flows. J. Am. Chem. Soc. 2008, 130(1), 44-45.
121. Chandler, D. Interfaces and the driving force of hydrophobic assembly. Nature, 2005, 437(7059), 640-647.
122. Guex, N.; Peitsch, M. C. SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling. Electrophoresis, 1997, 18(15), 2714-2723.