Controlling 2-arachidonoylglycerol metabolism as an anti-inflammatory strategy

Drug Discovery Today

Volumn 19, Issue 3, 2014, Pages 295-304

  Alhouayek, Mireille ^a   Masquelier, Julien ^a   Muccioli, Giulio G ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 HEXAMETHYLENEDICARBAMIC ACID BIS(CYCLOHEXANONE OXIME) ESTER; 2 ARACHIDONOYLGLYCEROL; ACYLGLYCEROL LIPASE; ANTIINFLAMMATORY AGENT; CANNABINOID RECEPTOR; CYCLOHEXYLCARBAMIC ACID 3' CARBAMOYLBIPHENYL 3 YL ESTER; CYCLOOXYGENASE 2; ENDOCANNABINOID; FATTY ACID AMIDASE; ICOSANOID; JJKK 0488; JZL 184; JZL 195; KT 109; KT 172; LIPOPROTEIN LIPASE; LIPOXYGENASE; MJN 110; MONOACYLGLYCEROL; O 7460; OMDM 169; OMDM 188; PHOSPHOLIPASE C; UNCLASSIFIED DRUG; URB 602; WWL 123; WWL 70; 2-ARACHIDONYLGLYCEROL; ACYLGLYCEROL; ARACHIDONIC ACID DERIVATIVE; ESTER; PROSTAGLANDIN;

ANTIINFLAMMATORY ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; CELL INFILTRATION; CELL MIGRATION; CELL PROLIFERATION; CYTOKINE PRODUCTION; CYTOKINE RELEASE; DRUG MECHANISM; ENZYME ACTIVITY; HUMAN; HYDROLYSIS; ICOSANOID METABOLISM; INFLAMMATION; MACROPHAGE ACTIVATION; NEUTROPHIL; NONHUMAN; REVIEW; ANIMAL; DRUG DESIGN; METABOLISM; PATHOPHYSIOLOGY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ARACHIDONIC ACIDS; CYCLOOXYGENASE 2; DRUG DESIGN; ENDOCANNABINOIDS; ESTERS; GLYCERIDES; HUMANS; INFLAMMATION; PROSTAGLANDINS; RECEPTORS, CANNABINOID;

EID: 84896404023     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2013.07.009     Document Type: Review

References (79)

1. 2+ dependency for triggering retrograde endocannabinoid signal Neuron 45 2005 257 268 (Pubitemid 40128119)
2. K.L. Hsu et al. DAGLbeta inhibition perturbs a lipid network involved in macrophage inflammatory responses Nat. Chem. Biol. 8 2012 999 1007
3. L.C. Gregg et al. Activation of type 5 metabotropic glutamate receptors and diacylglycerol lipase-alpha initiates 2-arachidonoylglycerol formation and endocannabinoid-mediated analgesia J. Neurosci. 32 2012 9457 9468
4. T. Bisogno et al. Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain J. Cell Biol. 163 2003 463 468 (Pubitemid 37429860)
5. G.G. Muccioli Endocannabinoid biosynthesis and inactivation, from simple to complex Drug Discov. Today 15 2010 474 483
6. J.L. Blankman et al. A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol Chem. Biol. 14 2007 1347 1356 (Pubitemid 350257008)
7. G.G. Muccioli et al. Identification of a novel endocannabinoid- hydrolyzing enzyme expressed by microglial cells J. Neurosci. 27 2007 2883 2889 (Pubitemid 46438968)
8. W.R. Marrs et al. The serine hydrolase ABHD6 controls the accumulation and efficacy of 2-AG at cannabinoid receptors Nat. Neurosci. 13 2010 951 957
9. K.C. Duggan et al. (R)-Profens are substrate-selective inhibitors of endocannabinoid oxygenation by COX-2 Nat. Chem. Biol. 7 2011 803 809
10. D.K. Nomura et al. Endocannabinoid hydrolysis generates brain prostaglandins that promote neuroinflammation Science 334 2011 809 813
11. C.A. Rouzer, and L.J. Marnett Endocannabinoid oxygenation by cyclooxygenases, lipoxygenases, and cytochromes P450: cross-talk between the eicosanoid and endocannabinoid signaling pathways Chem. Rev. 111 2011 5899 5921
12. P. Raman et al. 15-Deoxy-delta12,14-prostaglandin J2-glycerol ester, a putative metabolite of 2-arachidonyl glycerol, activates peroxisome proliferator activated receptor gamma Mol. Pharmacol. 80 2011 201 209
13. S.S. Hu et al. Prostaglandin E2 glycerol ester, an endogenous COX-2 metabolite of 2-arachidonoylglycerol, induces hyperalgesia and modulates NFkappaB activity Br. J. Pharmacol. 153 2008 1538 1549 (Pubitemid 351481525)
14. K.B. Hansen et al. 2-Oleoyl glycerol is a GPR119 agonist and signals GLP-1 release in humans J. Clin. Endocrinol. Metab. 96 2011 E1409 E1417
15. M. Feledziak et al. Inhibitors of the endocannabinoid-degrading enzymes, or how to increase endocannabinoid's activity by preventing their hydrolysis Recent Pat. CNS Drug Discov. 7 2012 49 70
16. A.G. Hohmann et al. An endocannabinoid mechanism for stress-induced analgesia Nature 435 2005 1108 1112 (Pubitemid 40910518)
17. A.R. King et al. URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices Chem. Biol. 14 2007 1357 1365 (Pubitemid 350257009)
18. J.Z. Long et al. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects Nat. Chem. Biol. 5 2009 37 44
19. J.Z. Long et al. Characterization of monoacylglycerol lipase inhibition reveals differences in central and peripheral endocannabinoid metabolism Chem. Biol. 16 2009 744 753
20. J.E. Schlosburg et al. Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system Nat. Neurosci. 13 2010 1113 1119
21. J.W. Chang et al. Highly selective inhibitors of monoacylglycerol lipase bearing a reactive group that is bioisosteric with endocannabinoid substrates Chem. Biol. 19 2012 579 588
22. W. Li et al. A functional proteomic strategy to discover inhibitors for uncharacterized hydrolases J. Am. Chem. Soc. 129 2007 9594 9595 (Pubitemid 47237463)
23. D.A. Bachovchin et al. Superfamily-wide portrait of serine hydrolase inhibition achieved by library-versus-library screening Proc. Natl. Acad. Sci. U. S. A. 107 2010 20941 20946
24. S. Maione et al. Elevation of endocannabinoid levels in the ventrolateral periaqueductal grey through inhibition of fatty acid amide hydrolase affects descending nociceptive pathways via both cannabinoid receptor type 1 and transient receptor potential vanilloid type-1 receptors J. Pharmacol. Exp. Ther. 316 2006 969 982 (Pubitemid 43345268)
25. S. Kathuria et al. Modulation of anxiety through blockade of anandamide hydrolysis Nat. Med. 9 2003 76 81 (Pubitemid 36098263)
26. K. Ahn et al. Discovery and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain Chem. Biol. 16 2009 411 420
27. H.S. Hoover et al. Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling Bioorg. Med. Chem. Lett. 18 2008 5838 5841
28. E.V. Berdyshev et al. Activation of PAF receptors results in enhanced synthesis of 2-arachidonoylglycerol (2-AG) in immune cells FASEB J. 15 2001 2171 2178 (Pubitemid 32927934)
29. 2 receptor-dependent mechanism Mol. Pharmacol. 65 2004 999 1007 (Pubitemid 38420506)
30. M. Lee et al. Effects of putative cannabinoid receptor ligands, anandamide and 2-arachidonyl-glycerol, on immune function in B6C3F1 mouse splenocytes J. Pharmacol. Exp. Ther. 275 1995 529 536 (Pubitemid 26025542)
31. R. Gallily et al. 2-Arachidonylglycerol, an endogenous cannabinoid, inhibits tumor necrosis factor-alpha production in murine macrophages, and in mice Eur. J. Pharmacol. 406 2000 R5 R7
32. F. Facchinetti et al. Cannabinoids ablate release of TNFalpha in rat microglial cells stimulated with lypopolysaccharide Glia 41 2003 161 168 (Pubitemid 36262193)
33. C.E. Rockwell et al. 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 2006 101 111
34. A. Lourbopoulos et al. Administration of 2-arachidonoylglycerol ameliorates both acute and chronic experimental autoimmune encephalomyelitis Brain Res. 1390 2011 126 141
35. G. Krishnan, and N. Chatterjee Endocannabinoids alleviate proinflammatory conditions by modulating innate immune response in muller glia during inflammation Glia 60 2012 1629 1645
36. J. Zhang, and C. Chen Endocannabinoid 2-arachidonoylglycerol protects neurons by limiting COX-2 elevation J. Biol. Chem. 283 2008 22601 22611
37. H. Du et al. Inhibition of COX-2 expression by endocannabinoid 2-arachidonoylglycerol is mediated via PPAR-gamma Br. J. Pharmacol. 163 2011 1533 1549
38. S. Oka et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces the migration of EoL-1 human eosinophilic leukemia cells and human peripheral blood eosinophils J. Leukoc. Biol. 76 2004 1002 1009 (Pubitemid 39458711)
39. R. Kurihara et al. Effects of peripheral cannabinoid receptor ligands on motility and polarization in neutrophil-like HL60 cells and human neutrophils J. Biol. Chem. 281 2006 12908 12918 (Pubitemid 43855384)
40. 2 Mol. Pharmacol. 73 2008 441 450 (Pubitemid 351159214)
41. N.A. Balenga et al. GPR55 regulates cannabinoid 2 receptor-mediated responses in human neutrophils Cell Res. 21 2011 1452 1469
42. M. Gokoh et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, enhances the adhesion of HL-60 cells differentiated into macrophage-like cells and human peripheral blood monocytes FEBS Lett. 579 2005 6473 6478 (Pubitemid 41612170)
43. D. Baker et al. Endocannabinoids control spasticity in a multiple sclerosis model FASEB J. 15 2001 300 302
44. M. van der Stelt et al. A role for endocannabinoids in the generation of parkinsonism and levodopa-induced dyskinesia in MPTP-lesioned non-human primate models of Parkinson's disease FASEB J. 19 2005 1140 1142 (Pubitemid 40946444)
45. 1 cannabinoid receptors are involved in neuroprotection via NF-kappa B inhibition J. Cereb. Blood Flow Metab. 25 2005 477 484
46. F. Loria et al. Study of the regulation of the endocannabinoid system in a virus model of multiple sclerosis reveals a therapeutic effect of palmitoylethanolamide Eur. J. Neurosci. 28 2008 633 641
47. D. Panikashvili et al. The endocannabinoid 2-AG protects the blood-brain barrier after closed head injury and inhibits mRNA expression of proinflammatory cytokines Neurobiol. Dis. 22 2006 257 264
48. A. Witting et al. Experimental autoimmune encephalomyelitis disrupts endocannabinoid-mediated neuroprotection Proc. Natl. Acad. Sci. U. S. A. 103 2006 6362 6367
49. D. Centonze et al. The endocannabinoid system is dysregulated in multiple sclerosis and in experimental autoimmune encephalomyelitis Brain 130 2007 2543 2553 (Pubitemid 47511703)
50. M. Di Filippo et al. Abnormalities in the cerebrospinal fluid levels of endocannabinoids in multiple sclerosis J. Neurol. Neurosurg. Psychiatry 79 2008 1224 1229
51. D. De Filippis et al. Levels of endocannabinoids and palmitoylethanolamide and their pharmacological manipulation in chronic granulomatous inflammation in rats Pharmacol. Res. 61 2010 321 328
52. F. Comelli et al. The inhibition of monoacylglycerol lipase by URB602 showed an anti-inflammatory and anti-nociceptive effect in a murine model of acute inflammation Br. J. Pharmacol. 152 2007 787 794 (Pubitemid 350034978)
53. S. Ghosh et al. The monoacylglycerol lipase inhibitor JZL184 suppresses inflammatory pain in the mouse carrageenan model Life Sci. 92 2013 498 505
54. M. Alhouayek et al. Increasing endogenous 2-arachidonoylglycerol levels counteracts colitis and related systemic inflammation FASEB J. 25 2011 2711 2721
55. M. Alhouayek, and G.G. Muccioli The endocannabinoid system in inflammatory bowel diseases: from pathophysiology to therapeutic opportunity Trends Mol. Med. 18 2012 615 625
56. D.M. Kerr et al. The monoacylglycerol lipase inhibitor JZL184 attenuates LPS-induced increases in cytokine expression in the rat frontal cortex and plasma: differential mechanisms of action Br. J. Pharmacol. 169 2013 808 819
57. F. Tchantchou, and Y. Zhang Selective inhibition of alpha/beta-hydrolase domain 6 attenuates neurodegeneration, alleviates blood brain barrier breakdown, and improves functional recovery in a mouse model of traumatic brain injury J. Neurotrauma 30 2013 565 579
58. 2 receptor and its endogenous ligand 2-arachidonoylglycerol in oxazolone-induced contact dermatitis in mice J. Immunol. 177 2006 8796 8805 (Pubitemid 44893846)
59. D.C. McVey et al. Endocannabinoids induce ileitis in rats via the capsaicin receptor (VR1) J. Pharmacol. Exp. Ther. 304 2003 713 722 (Pubitemid 36152349)
60. F. Montecucco, and V. Di Marzo At the heart of the matter: the endocannabinoid system in cardiovascular function and dysfunction Trends Pharmacol. Sci. 33 2012 331 340
61. T. Bisogno et al. A novel fluorophosphonate inhibitor of the biosynthesis of the endocannabinoid 2-arachidonoylglycerol with potential anti-obesity effects Br. J. Pharmacol. 169 2013 784 793
62. O.P. Keown et al. 2-Arachidonyl glycerol activates platelets via conversion to arachidonic acid and not by direct activation of cannabinoid receptors Br. J. Clin. Pharmacol. 70 2010 180 188
63. F. Chouinard et al. The endocannabinoid 2-arachidonoyl-glycerol activates human neutrophils: critical role of its hydrolysis and de novo leukotriene B4 biosynthesis J. Immunol. 186 2011 3188 3196
64. J.J. Gopez et al. Cyclooxygenase-2-specific inhibitor improves functional outcomes, provides neuroprotection, and reduces inflammation in a rat model of traumatic brain injury Neurosurgery 56 2005 590 604
65. A. Telleria-Diaz et al. Spinal antinociceptive effects of cyclooxygenase inhibition during inflammation: involvement of prostaglandins and endocannabinoids Pain 148 2010 26 35
66. H. Guhring et al. A role for endocannabinoids in indomethacin-induced spinal antinociception Eur. J. Pharmacol. 454 2002 153 163 (Pubitemid 35287474)
67. M. Ates et al. Intrathecally applied flurbiprofen produces an endocannabinoid-dependent antinociception in the rat formalin test Eur. J. Neurosci. 17 2003 597 604 (Pubitemid 36255896)
68. L.E. Staniaszek et al. Effects of COX-2 inhibition on spinal nociception: the role of endocannabinoids Br. J. Pharmacol. 160 2010 669 676
69. J.J. Prusakiewicz et al. Differential sensitivity and mechanism of inhibition of COX-2 oxygenation of arachidonic acid and 2-arachidonoylglycerol by ibuprofen and mefenamic acid Biochemistry 48 2009 7353 7355
70. J. Lotsch et al. Effects of flurbiprofen enantiomers on pain-related chemo-somatosensory evoked potentials in human subjects Br. J. Clin. Pharmacol. 40 1995 339 346
71. P. Bishay et al. R-flurbiprofen reduces neuropathic pain in rodents by restoring endogenous cannabinoids PLoS ONE 5 2010 e10628
72. C.S. Nirodi et al. The glyceryl ester of prostaglandin E2 mobilizes calcium and activates signal transduction in RAW264.7 cells Proc. Natl. Acad. Sci. U. S. A. 101 2004 1840 1845 (Pubitemid 38228978)
73. N. Aaltonen et al. Piperazine and piperidine triazole ureas as ultrapotent and highly selective inhibitors of monoacylglycerol lipase Chem. Biol. 20 2013 379 390
74. J.W. Chang et al. Proteome-wide reactivity profiling identifies diverse carbamate chemotypes tuned for serine hydrolase inhibition ACS Chem. Biol. 2013 10.1021/cb400261h
75. M.J. Niphakis et al. Evaluation of NHS carbamates as a potent and selective class of endocannabinoid hydrolase inhibitors ACS Chem. Neurosci. 2013 10.1021/cn400116z
76. J.Z. Long et al. Dual blockade of FAAH and MAGL identifies behavioral processes regulated by endocannabinoid crosstalk in vivo Proc. Natl. Acad. Sci. U. S. A. 106 2009 20270 20275
77. T. Bisogno et al. Development of a potent inhibitor of 2-arachidonoylglycerol hydrolysis with antinociceptive activity in vivo Biochim. Biophys. Acta 1791 2009 53 60
78. D. Navia-Paldanius et al. Biochemical and pharmacological characterization of human alpha/beta-hydrolase domain containing 6 (ABHD6) and 12 (ABHD12) J. Lipid Res. 53 2012 2413 2424
79. G. Ortar et al. Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism J. Med. Chem. 51 2008 6970 6979