Anti-proliferative effect of a putative endocannabinoid, 2-arachidonylglyceryl ether in prostate carcinoma cells

Prostaglandins and Other Lipid Mediators

Volumn 94, Issue 1-2, 2011, Pages 34-43

  Nithipatikom, Kasem ^a   Isbell, Marilyn A ^a   Endsley, Michael P ^a   Woodliff, Jeffrey E ^a   Campbell, William B ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

2 Arachidonylglyceryl ether (noladin ether); Cannabinoid receptor; Endocannabinoid; Proliferation; Prostate cancer

Indexed keywords

2 CHLORO 5 NITROBENZANILIDE; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; ANANDAMIDE; CYCLIN D1; CYCLIN E; ENDOCANNABINOID; NOLADIN ETHER; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PERTUSSIS TOXIN; RIMONABANT; TRANSCRIPTION FACTOR RELA;

ARTICLE; CARCINOMA CELL; CELL CYCLE ARREST; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL GROWTH; CELL PROLIFERATION; DOWN REGULATION; HUMAN; HUMAN CELL; HYDROLYSIS; PROSTATE CARCINOMA;

ANILIDES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CYCLIN D1; CYCLIN E; ENDOCANNABINOIDS; GLYCERIDES; HUMANS; MALE; NF-KAPPA B; PPAR GAMMA; PROSTATE; PROSTATIC NEOPLASMS;

EID: 79551564914     PISSN: 10988823     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.prostaglandins.2010.12.002     Document Type: Article

References (62)

1. W.A. Devane, L. Hanus, and A. Breuer Isolation and structure of a brain constituent that binds to the cannabinoid receptor Science 258 5090 1992 1946 1949
2. R. Mechoulam, S. Ben-Shabat, and L. Hanus Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors Biochem Pharmacol 50 1 1995 83 90
3. T. Sugiura, S. Kondo, and A. Sukagawa 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain Biochem Biophys Res Commun 215 1 1995 89 97
4. A.A. Izzo, G. Aviello, and S. Petrosino Increased endocannabinoid levels reduce the development of precancerous lesions in the mouse colon J Mol Med 86 1 2008 89 98
5. A. Ligresti, T. Bisogno, and I. Matias Possible endocannabinoid control of colorectal cancer growth Gastroenterology 125 3 2003 677 687
6. D. Parolaro, P. Massi, T. Rubino, and E. Monti Endocannabinoids in the immune system and cancer Prostaglandins Leukot Essent Fatty Acids 66 2-3 2002 319 332
7. M. Bifulco, C. Laezza, M. Valenti, A. Ligresti, G. Portella, and V. Di Marzo A new strategy to block tumor growth by inhibiting endocannabinoid inactivation FASEB J 18 13 2004 1606 1608
8. M. Bifulco, C. Laezza, P. Gazzerro, and F. Pentimalli Endocannabinoids as emerging suppressors of angiogenesis and tumor invasion Oncol Rep 17 4 2007 813 816 [review]
9. M. Bifulco, and V. Di Marzo Targeting the endocannabinoid system in cancer therapy: a call for further research Nat Med 8 6 2002 547 550
10. M. Bifulco, A.M. Malfitano, S. Pisanti, and C. Laezza Endocannabinoids in endocrine and related tumours Endocr Relat Cancer 15 2 2008 391 408
11. J. Flygare, and B. Sander The endocannabinoid system in cancer-potential therapeutic target? Semin Cancer Biol 18 3 2008 176 189
12. D. Melck, L. De Petrocellis, and P. Orlando 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
13. C. Grimaldi, S. Pisanti, and C. Laezza Anandamide inhibits adhesion and migration of breast cancer cells Exp Cell Res 312 4 2006 363 373
14. C. Laezza, S. Pisanti, A.M. Malfitano, and M. Bifulco The anandamide analog, Met-F-AEA, controls human breast cancer cell migration via the RHOA/RHO kinase signaling pathway Endocr Relat Cancer 15 4 2008 965 974
15. 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
16. K. Nithipatikom, M.P. Endsley, and M.A. Isbell 2-Arachidonoylglycerol: a novel inhibitor of androgen-independent prostate cancer cell invasion Cancer Res 64 24 2004 8826 8830
17. M.P. Endsley, R. Thill, and I. Choudhry Expression and function of fatty acid amide hydrolase in prostate cancer Int J Cancer 123 6 2008 1318 1326
18. 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
19. V. Di Marzo, T. Bisogno, and L. De Petrocellis Biosynthesis and inactivation of the endocannabinoid 2-arachidonoylglycerol in circulating and tumoral macrophages Eur J Biochem 264 1 1999 258 267
20. M. Bari, N. Battista, F. Fezza, V. Gasperi, and M. Maccarrone New insights into endocannabinoid degradation and its therapeutic potential Mini Rev Med Chem 6 3 2006 257 268
21. T.P. Dinh, D. Carpenter, and F.M. Leslie Brain monoglyceride lipase participating in endocannabinoid inactivation Proc Natl Acad Sci USA 99 16 2002 10819 10824
22. T.P. Dinh, T.F. Freund, and D. Piomelli A role for monoglyceride lipase in 2-arachidonoylglycerol inactivation Chem Phys Lipids 121 1-2 2002 149 158
23. T.P. Dinh, S. Kathuria, and D. Piomelli RNA interference suggests a primary role for monoacylglycerol lipase in the degradation of the endocannabinoid 2-arachidonoylglycerol Mol Pharmacol 66 5 2004 1260 1264
24. M. Hughes-Fulford, C.F. Li, J. Boonyaratanakornkit, and S. Sayyah Arachidonic acid activates phosphatidylinositol 3-kinase signaling and induces gene expression in prostate cancer Cancer Res 66 3 2006 1427 1433
25. M.P. Endsley, N. Aggarwal, and M.A. Isbell Diverse roles of 2-arachidonoylglycerol in invasion of prostate carcinoma cells: location, hydrolysis and 12-lipoxygenase metabolism Int J Cancer 121 5 2007 984 991
26. T. Hussain, S. Gupta, and H. Mukhtar Cyclooxygenase-2 and prostate carcinogenesis Cancer Lett 191 2 2003 125 135
27. H. Fujita, K. Koshida, and E.T. Keller Cyclooxygenase-2 promotes prostate cancer progression Prostate 53 3 2002 232 240
28. D. Nie, M. Che, D. Grignon, K. Tang, and K.V. Honn Role of eicosanoids in prostate cancer progression Cancer Metastasis Rev 20 3-4 2001 195 206
29. N. Pommery, T. Taverne, and A. Telliez New COX-2/5-LOX inhibitors: apoptosis-inducing agents potentially useful in prostate cancer chemotherapy J Med Chem 47 25 2004 6195 6206
30. S. Petrosino, and V. Di Marzo FAAH and MAGL inhibitors: therapeutic opportunities from regulating endocannabinoid levels Curr Opin Investig Drugs 11 1 2010 51 62
31. P. Pacher, S. Batkai, and G. Kunos The endocannabinoid system as an emerging target of pharmacotherapy Pharmacol Rev 58 3 2006 389 462
32. K. Nithipatikom, M.P. Endsley, M.A. Isbell, C.E. Wheelock, B.D. Hammock, and W.B. Campbell A new class of inhibitors of 2-arachidonoylglycerol hydrolysis and invasion of prostate cancer cells Biochem Biophys Res Commun 332 4 2005 1028 1033
33. L. Hanus, S. Abu-Lafi, and E. Fride 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor Proc Natl Acad Sci USA 98 7 2001 3662 3665
34. G. Appendino, A. Ligresti, A. Minassi, N. Daddario, T. Bisogno, and V. Di Marzo Homologues and isomers of noladin ether, a putative novel endocannabinoid: interaction with rat cannabinoid CB(1) receptors Bioorg Med Chem Lett 13 1 2003 43 46
35. F. Fezza, T. Bisogno, A. Minassi, G. Appendino, R. Mechoulam, and V. Di Marzo Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues FEBS Lett 513 2-3 2002 294 298
36. K. Laine, K. Jarvinen, R. Mechoulam, A. Breuer, and T. Jarvinen Comparison of the enzymatic stability and intraocular pressure effects of 2-arachidonylglycerol and noladin ether, a novel putative endocannabinoid Invest Ophthalmol Vis Sci 43 10 2002 3216 3222
37. Y. Suhara, H. Takayama, S. Nakane, T. Miyashita, K. Waku, and T. Sugiura Synthesis and biological activities of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand, and its metabolically stable ether-linked analogues Chem Pharm Bull (Tokyo) 48 7 2000 903 907
38. M. Steffens, A. Schulze-Bonhage, R. Surges, and T.J. Feuerstein Fatty acid amidohydrolase in human neocortex-activity in epileptic and non-epileptic brain tissue and inhibition by putative endocannabinoids Neurosci Lett 385 1 2005 13 17
39. S. Oka, A. Tsuchie, and A. Tokumura Ether-linked analogue of 2-arachidonoylglycerol (noladin ether) was not detected in the brains of various mammalian species J Neurochem 85 6 2003 1374 1381
40. D. Richardson, C.A. Ortori, V. Chapman, D.A. Kendall, and D.A. Barrett Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry Anal Biochem 360 2 2007 216 226
41. M. Steffens, J. Zentner, J. Honegger, and T.J. Feuerstein Binding affinity and agonist activity of putative endogenous cannabinoids at the human neocortical CB1 receptor Biochem Pharmacol 69 1 2005 169 178
42. J.L. Shoemaker, B.K. Joseph, M.B. Ruckle, P.R. Mayeux, and P.L. Prather The endocannabinoid noladin ether acts as a full agonist at human CB2 cannabinoid receptors J Pharmacol Exp Ther 314 2 2005 868 875
43. C.E. Rockwell, N.T. Snider, J.T. Thompson, J.P. Vanden Heuvel, and N.E. Kaminski Interleukin-2 suppression by 2-arachidonyl glycerol is mediated through peroxisome proliferator-activated receptor gamma independently of cannabinoid receptors 1 and 2 Mol Pharmacol 70 1 2006 101 111
44. M.A. Lea, M. Sura, and C. Desbordes Inhibition of cell proliferation by potential peroxisome proliferator-activated receptor (PPAR) gamma agonists and antagonists Anticancer Res 24 5A 2004 2765 2771
45. J.S. Annicotte, I. Iankova, and S. Miard Peroxisome proliferator- activated receptor gamma regulates E-cadherin expression and inhibits growth and invasion of prostate cancer Mol Cell Biol 26 20 2006 7561 7574
46. N. Pitulis, E. Papageorgiou, R. Tenta, P. Lembessis, and M. Koutsilieris IL-6 and PPARgamma signalling in human PC-3 prostate cancer cells Anticancer Res 29 6 2009 2331 2337
47. S.E. Campbell, P.R. Musich, and S.G. Whaley Gamma tocopherol upregulates the expression of 15-S-HETE and induces growth arrest through a PPAR gamma-dependent mechanism in PC-3 human prostate cancer cells Nutr Cancer 61 5 2009 649 662
48. J.M. Dahlman, J. Wang, N. Bakkar, and D.C. Guttridge The RelA/p65 subunit of NF-kappaB specifically regulates cyclin D1 protein stability: implications for cell cycle withdrawal and skeletal myogenesis J Cell Biochem 106 1 2009 42 51
49. D.J. Son, M.H. Park, and S.J. Chae Inhibitory effect of snake venom toxin from Vipera lebetina turanica on hormone-refractory human prostate cancer cell growth: induction of apoptosis through inactivation of nuclear factor kappaB Mol Cancer Ther 6 2 2007 675 683
50. C.E. Wheelock, T.F. Severson, and B.D. Hammock Synthesis of new carboxylesterase inhibitors and evaluation of potency and water solubility Chem Res Toxicol 14 12 2001 1563 1572
51. C.E. Wheelock, M.E. Colvin, and I. Uemura Use of ab initio calculations to predict the biological potency of carboxylesterase inhibitors J Med Chem 45 25 2002 5576 5593
52. W.S. Edgemond, M.J. Greenberg, P.J. McGinley, S. Muthian, W.B. Campbell, and C.J. Hillard Synthesis and characterization of diazomethylarachidonyl ketone: an irreversible inhibitor of N-arachidonylethanolamine amidohydrolase J Pharmacol Exp Ther 286 1 1998 184 190
53. 2-terminal kinase J Biol Chem 278 43 2003 42660 42667
54. P.F. Kue, and Y. Daaka Essential role for G proteins in prostate cancer cell growth and signaling J Urol 164 6 2000 2162 2167
55. T. Lyons-Darden, and Y. Daaka Requirement for G proteins in insulin-like growth factor-I-induced growth of prostate cells J Mol Endocrinol 33 1 2004 165 173
56. R.D. Price, T. Oe, T. Yamaji, and N. Matsuoka A simple, flexible, nonfluorescent system for the automated screening of neurite outgrowth J Biomol Screen 11 2 2006 155 164
57. G.W. Tew, E.L. Lorimer, T.J. Berg, H. Zhi, R. Li, and C.L. Williams SmgGDS regulates cell proliferation, migration, and NF-{kappa}B transcriptional activity in non-small cell lung carcinoma J Biol Chem 283 2 2008 963 976
58. D. Nagata, H. Yoshihiro, and M. Nakanishi Peroxisome proliferator- activated receptor-gamma and growth inhibition by its ligands in prostate cancer Cancer Detect Prev 32 3 2008 259 266
59. M. Hughes-Fulford, Y. Chen, and R.R. Tjandrawinata Fatty acid regulates gene expression and growth of human prostate cancer PC-3 cells Carcinogenesis 22 5 2001 701 707
60. M. Duncan, P. Millns, D. Smart, J.E. Wright, D.A. Kendall, and V. Ralevic Noladin ether, a putative endocannabinoid, attenuates sensory neurotransmission in the rat isolated mesenteric arterial bed via a non-CB1/CB2 G(i/o) linked receptor Br J Pharmacol 142 3 2004 509 518
61. A. Mahadevan, and R.K. Razdan Further advances in the synthesis of endocannabinoid-related ligands AAPS J 7 2 2005 E496 E502
62. J. Juntunen, J. Vepsalainen, R. Niemi, K. Laine, and T. Jarvinen Synthesis, in vitro evaluation, and intraocular pressure effects of water-soluble prodrugs of endocannabinoid noladin ether J Med Chem 46 23 2003 5083 5086