2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces the migration of EoL-1 human eosinophilic leukemia cells and human peripheral blood eosinophils

Journal of Leukocyte Biology

Volumn 76, Issue 5, 2004, Pages 1002-1009

  Oka, Saori ^a   Ikeda, Shinobu ^a   Kishimoto, Seishi ^a   Gokoh, Maiko ^a   Yanagimoto, Shin ^a   Waku, Keizo ^a   Sugiura, Takayuki ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

Allergy; Anandamide; Chemotaxis; Lipid mediators; Monoacylglycerol

Indexed keywords

2 ARCHIDONOYLGLYCEROL; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; ANANDAMIDE; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR; DRONABINOL; LIGAND; UNCLASSIFIED DRUG;

ALLERGY; ARTICLE; CELL MIGRATION; CELL MOTILITY; DRUG EFFECT; EOSINOPHIL; EOSINOPHILIC LEUKEMIA; GLIA CELL; HUMAN; HUMAN CELL; LEUKEMIA CELL; LYMPHOID TISSUE; NATURAL KILLER CELL; NEUTROPHIL; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; RECEPTOR BINDING; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SYNAPTIC TRANSMISSION;

ARACHIDONIC ACID; ARACHIDONIC ACIDS; BORNANES; CELL LINE, TUMOR; CHEMOTAXIS, LEUKOCYTE; EOSINOPHILS; GLYCERIDES; GTP-BINDING PROTEIN ALPHA SUBUNITS, GI-GO; HUMANS; HYPEREOSINOPHILIC SYNDROME; HYPERSENSITIVITY; NEUTROPHILS; PERTUSSIS TOXIN; POLYUNSATURATED ALKAMIDES; PYRAZOLES; RECEPTOR, CANNABINOID, CB2; RNA, MESSENGER;

EID: 7644244850     PISSN: 07415400     EISSN: None     Source Type: Journal    
DOI: 10.1189/jlb.0404252     Document Type: Article

References (56)

1. Dewey, W. L. (1986) Cannabinoid pharmacology. Pharmacol. Rev, 38, 151-178.
2. Matsuda, L. A., Lolait, S. J., Brownstein, M. J., Young, A. C., Bonner, T. I. (1990) Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346, 561-564.
3. Herkenham, M. (1995) Localization of cannabinoid receptors in brain and periphery. In Cannabinoid Receptors (R. G. Pertwee, ed.). London, UK, Academic, 145-166.
4. Munro, S., Thomas. K. L., Abu-Shaar, M. (1993) Molecular characterization of a peripheral receptor for cannabinoids. Nature 365, 61-65.
5. Di Marzo, V., Melck, D., Bisogno, T., De Petrocellis, L. (1998) Endocannabinoids, endogenous cannabinoid receptor ligands with neuromodulatory action. Trends Neurosci. 21, 521-528.
6. Schlicker, E., Kathmann, M. (2001) Modulation of transmitter release via presynaptic cannabinoid receptors. Trends Pharmacol. Sci. 22, 565-572.
7. Klein, T. W., Newton, C., Friedman, H. (1998) Cannabinoid receptors and immunity. Immunol. Today 19, 373-381.
8. Berdyshev, E. V. (2000) Cannabinoid receptors and the regulation of immune response. Chem. Phys. Lipids 108, 169-190.
9. Parolaro, D., Massi, P., Rubino, T., Monti, E. (2002) Endocannabinoids in the immune system and cancer. Prostaglandins Leukot. Essent. Fatty Acids 66, 319-332.
10. Cabral, G. A. (2002) Marijuana and cannabinoid effects on immunity and AIDS. In Biology of Marijuana (E. S. Onaivi, ed.), London. UK, Taylor & Francis, 282-307.
11. Klein, T. W., Larsen, C. K., Lu, L., Perkins, L., Nong, L., Friedman, H. (2003) The cannabinoid system and immune modulation. J. Leukoc. Biol. 74, 486-496.
12. Lee, M., Yang, K. H., Kaminski, N. E. (1995) Effects of putative cannabinoid receptor ligands, anandamide and 2-arachidonyl-glycerol, on immune function in B6C3F1 mouse splenocytes. J. Pharmacol. Exp. Ther. 275, 529-536.
13. Ouyang, Y., Hwang, S. G., Han, S. H., Kaminski, N. E. (1998) Suppression of interleukin-2 by the putative endogenous cannabinoid 2-arachidonyl-glycerol is mediated through down-regulation of the nuclear factor of activated T cells. Mol. Pharmacol. 53, 676-683.
14. Jbilo, O., Derocq, J. M., Segui, M., Le Fur, G., Casellas, P. (1999) Stimulation of peripheral cannabinoid receptor CB2 induces MCP-1 and IL-8 gene expression in human promyelocytic cell line HL60. FEBS Lett. 448, 273-277.
15. Carayon, P., Marchand, J., Dussossoy, D., Derocq, J. M., Jbilo, O., Bord, A., Bouaboula, M., Galiegue, S., Mondiere, P., Penarier, G., Le Fur, G., Defrance, T., Casellas, P, (1998) Modulation and functional involvement of CB2 peripheral cannabinoid receptors during B-cell differentiation. Blood 92, 3605-3615.
16. McCoy, K. L., Matveyeva, M., Carlisle, S. J., Cabral, G. A. (1999) Cannabinoid inhibition of the processing of intact lysozyme by macrophages: evidence for CB2 receptor participation. J. Pharmacol. Exp. Ther. 289, 1620-1625.
17. Gallily, R., Breuer, A., Mechoulam, R. (2000) 2-Arachidonylglycerol, an endogenous cannabinoid, inhibits tumor necrosis factor-α production in murine macrophages, and in mice. Eur. J. Pharmacol. 406, R5-R7.
18. Smith, S. R., Terminelli, C., Denhardt, G. (2000) Effects of cannabinoid receptor agonist and antagonist ligands on production of inflammatory cytokines and anti-inflammatory interleukin-10 in endotoxemic mice. J. Pharmacol. Exp. Ther. 293, 136-150.
19. Iwamura, H., Suzuki, H., Ueda, Y., Kaya, T., Inaba, T. (2001) In vitro and in vivo pharmacological characterization of JTE-907, a novel selective ligand for cannabinoid CB2 receptor. J. Pharmacol. Exp. Ther. 296, 420-425.
20. Chang, Y. H., Lee, S. T., Lin, W. W. (2001) Effects of cannabinoids on LPS-stimulated inflammatory mediator release from macrophages: involvement of eicosanoids. J. Cell. Biochem. 81, 715-723.
21. Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., Mechoulam, R. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946-1949.
22. Sugiura, T., Kondo, S., Sukagawa, A., Nakane, S., Shinoda, A., Itoh, K., Yamashita, A., Waku, K. (1995) 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem. Biophys. Res. Commun. 215, 89-97.
23. Mechoulam, R., Ben-Shabat, S., Hanus, L., Ligumsky, M., Kaminski, N. E., Schatz, A. R., Gopher, A., Almog, S., Martin, B. R., Compton, D. R., Pertwee, R. G., Griffin, G., Bayewitch, M., Barg, J., Vogel, Z. (1995) Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem. Pharmacol. 50, 83-90.
24. 2+ in neuroblastoma × glioma hybrid NG108-15 cells. Biochem. Biophys. Res. Commun. 229, 58-64.
25. 2+ transient in NG108-15 cells. J. Biochem. (Tokyo) 122, 890-895.
26. Sugiura, T., Kodaka, T., Nakane, S., Miyashita, T., Kondo, S., Suhara, Y., Takayama, H., Waku, K., Seki, C., Baba, N., Ishima, Y. (1999) 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. 274, 2794-2801.
27. Sugiura, T., Kondo, S., Kishimoto, S., Miyashita, T., Nakane, S., Kodaka, T., Suhara, Y., Takayama, H., Waku, K. (2000) Evidence that 2-arachidonoylglycerol but not N-palmitoylethanolamine or anandamide is the physiological ligand for the cannabinoid CB2 receptor. Comparison of the agonistic activities of various cannabinoid receptor ligands in HL-60 cells. J. Biol. Chem. 275, 605-612.
28. Mackie, K., Devane, W. A., Hille, B. (1993) Anandamide, an endogenous cannabinoid, inhibits calcium currents as a partial agonist in N18 neuroblastoma cells. Mol. Pharmacol. 44, 498-503.
29. Bayewitch, M., Levy, T. R., Barg, J., Mechoulam, R., Vogel, Z. (1995) The peripheral cannabinoid receptor: adenylate cyclase inhibition and G protein coupling. FEBS Lett. 375, 143-147.
30. Hillard, C. J. (2000) Biochemistry and pharmacology of the endocannabinoids arachidonylethanolamide and 2-arachidonylglycerol. Prostaglandins Other Lipid Mediat. 61, 3-18.
31. Gonsiorek, W., Lunn, C., Fan, X., Narula, S., Lundell, D., Hipkin, R. W. (2000) Endocannabinoid 2-arachidonyl glycerol is a full agonist through human type 2 cannabinoid receptor, antagonism by anandamide. Mol. Pharmacol. 57, 1045-1050.
32. Savinainen, J. R., Jarvinen, T., Laine, K., Laitinen, J. T. (2001) Despite substantial degradation, 2-arachidonoylglycerol is a potent full efficacy agonist mediating CB(1) receptor-dependent G-protein activation in rat cerebellar membranes. Br. J. Pharmacol. 134, 664-672.
33. Sugiura, T., Waku, K. (2000) 2-Arachidonoylglycerol and the cannabinoid receptors. Chem. Phys. Lipids 108, 89-106.
34. Sugiura, T., Waku, K. (2002) Cannabinoid receptors and their endogenous ligands. J. Biochem. (Tokyo) 132, 7-12.
35. Kobayashi, Y., Arai, S., Waku, K., Sugiura, T. (2001) Activation by 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand, of p42/44 mitogen-activated protein kinase in HL-60 cells. J. Biochem. (Tokyo) 129, 665-669.
36. Sugiura, T., Kishimoto, S., Oka, S., Gokoh, M., Waku, K. (2004) Metabolism and physiological significance of anandamide and 2- arachidonoylglycerol, endogenous cannabinoid receptor ligands. In Arachidonate Remodeling and inflammation (A. N. Fonteh, R. L. Wykle, eds.), Basel, Switzerland, Birkhauser Verlag, 211-237.
37. Derkinderen, P., Ledent, C., Parmentier, M., Girault, J. A. (2001) Cannabinoids activate p38 mitogen-activated protein kinases through CB1 receptors in hippocampus. J. Neurochem. 77, 957-960.
38. 1 cannabinoid receptor is coupled to the activation of c-Jun N-terminal kinase. Mol. Pharmacol. 58, 814-820.
39. Kishimoto, S., Gokoh, M., Oka, S., Muramatsu, M., Kajiwara, T., Waku, K., Sugiura, T. (2003) 2-Arachidonoylglycerol induces the migration of HL-60 cells differentiated into macrophage-like cells and human peripheral blood monocytes through the cannabinoid CB2 receptor-dependent mechanism. J. Biol. Chem. 278, 24469-24475.
40. Jorda, M. A., Verbakel, S. E., Valk, P. J., Vankan-Berkhoudt, Y. V., Maccarrone, M., Finazzi-Agro, A., Lowenberg, B., Delwel, R. (2002) Hematopoietic cells expressing the peripheral cannabinoid receptor migrate in response to the endocannabinoid 2-arachidonoylglycerol. Blood 99, 2786-2793.
41. Walter, L., Franklin, A., Witting, A., Wade, C., Xie, Y., Kunos, G., Mackie, K., Stella, N. (2003) Nonpsychotropic cannabinoid receptors regulate microglial cell migration. J. Neurosci. 23, 1398-1405.
42. Galiegue, S., Mary, S., Marchand, J., Dussossoy, D., Carriere, D., Carayon, P., Bouaboula, M., Shire, D., Le Fur, G., Casellas, P. (1995) Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur. J. Biochem. 232, 54-61.
43. Xia, L., Sperandio, M., Yago, T., McDaniel, J. M., Cummings, R. D., Pearson-White, S., Ley, K., McEver, R. P. (2002) P-selectin glycoprotein ligand-1-deficient mice have impaired leukocyte tethering to E-selectin under flow. J. Clin. Invest. 109, 939-950.
44. Bousquet, J., Chanez. P., Lacoste, J. Y., Barneon, G., Ghavanian, N., Enander, I., Venge, P., Ahlstedt, S., Simony-Lafontaine, J., Godard, P., Michel, F-B. (1990) Eosinophilic inflammation in asthma. N. Engl. J. Med. 323, 1033-1039.
45. Wardlaw, A. J., Moqbel, R., Kay, A. B. (1995) Eosinophils: biology and role in disease. Adv. Immunol. 60, 151-266.
46. Bisogno, T., Sepe, N., Melck, D., Maurelli, S., De Petrocellis, L., Di Marzo, V. (1997) Biosynthesis, release and degradation of the novel endogenous cannabimimetic metabolite 2-arachidonoylglycerol in mouse neuroblastoma cells. Biochem. J. 322, 671-677.
47. Di Marzo, V., Bisogno, T., Sugiura, T., Melck, D., De Petrocellis, L. (1998) The novel endogenous cannabinoid 2-arachidonoylglycerol is inactivated by neuronal and basophil-like cells, connections with anandamide. Biochem. J. 331, 15-19.
48. Boehme, S. A., Sullivan, S. K., Crowe, P. D., Santos, M., Conlon, P. J., Sriramarao, P., Bacon, K. B. (1999) Activation of mitogen-activated protein kinase regulates eotaxin-induced eosinophil migration. J. Immunol. 163, 1611-1618.
49. Kampen, G. T., Stafford, S., Adachi, T., Jinquan, T., Quan, S., Grant, J. A., Skov, P. S., Poulsen, L. K., Alam, R. (2000) Eotaxin induces degranulation and chemotaxis of eosinophils through the activation of ERK2 and p38 mitogen-activated protein kinases. Blood 95, 1911-1917.
50. Powell, W. S., Chung, D., Gravel, S. J. (1995) 5-Oxo-6,8,11,14- eicosatetraenoic acid is a potent stimulator of human eosinophil migration. J. Immunol. 154, 4123-4132.
51. Schwenk, U., Schroder, J. M. (1995) 5-Oxo-eicosanoids are potent eosinophil chemotactic factors. Functional characterization and structural requirements. J. Biol. Chem. 270, 15029-15036.
52. O'Flaherty, J. T., Kuroki, M., Nixon, A. B., Wijkander, J., Yee, E., Lee, S. L., Smitherman, P. K., Wykle, R. L., Daniel, L. W. (1996) 5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes. J. Immunol. 157, 336-342.
53. Morita, E., Schroder, J. M., Christophers, E. (1989) Differential sensitivities of purified human eosinophils and neutrophils to defined chemotaxins. Scand. J. Immunol. 29, 709-716.
54. Varga, K., Wagner, J. A., Bridgen, D. T., Kunos, G. (1998) Platelet- and macrophage-derived endogenous cannabinoids are involved in endotoxin-induced hypotension. FASEB J. 12, 1035-1044.
55. Di Marzo, V., Bisogno, T., De Petrocellis, L., Melck, D., Orlando, P., Wagner, J. A., Kunos, G. (1999) Biosynthesis and inactivation of the endocannabinoid 2-arachidonoylglycerol in circulating and tumoral macrophages. Eur. J. Biochem. 264, 258-267.
56. Berdyshev, E. V., Schmid, P. C., Krebsbach, R. J., Schmid, H. H. O. (2001) Activation of PAF receptors results in enhanced synthesis of 2-arachidonoylglycerol (2-AG) in immune cells. FASEB J. 15, 2171-2178.