Comparative biochemical characterization of the monoacylglycerol lipase inhibitor KML29 in brain, spinal cord, liver, spleen, fat and muscle tissue

Neuropharmacology

Volumn 91, Issue , 2015, Pages 148-156

  Pasquarelli, Noemi ^a,b   Porazik, Christoph ^a,b   Hanselmann, Johannes ^a   Weydt, Patrick ^a   Ferger, Boris ^b   Witting, Anke ^a  

^a UNIVERSITY OF ULM   (Germany)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

Author keywords

2 Arachidonoylglycerol; Central nervous system; Endocannabinoid; KML29; Monoacylglycerol lipase inhibitor

Indexed keywords

1,1,1,3,3,3 HEXAFLUOROPROPAN 2 YL 4 [BIS(BENZO[D][1,3]DIOXOL 5 YL)(HYDROXY)METHYL]PIPERIDINE 1 CARBOXYLATE; 2 ARACHIDONOYLGLYCEROL; ACYLGLYCEROL LIPASE; ACYLGLYCEROL LIPASE INHIBITOR; ARACHIDONIC ACID; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYTOSOLIC PHOSPHOLIPASE A2; FATTY ACID AMIDASE; PROSTAGLANDIN; UNCLASSIFIED DRUG; 1,1,1,3,3,3-HEXAFLUOROPROPAN-2-YL 4-(BIS(BENZO(D)(1,3)DIOXOL-5-YL)(HYDROXY)METHYL)PIPERIDINE-1-CARBOXYLATE; 1,3 BENZODIOXOLE DERIVATIVE; 2-ARACHIDONYLGLYCEROL; ACYLGLYCEROL; ANALGESIC AGENT; ARACHIDONIC ACID DERIVATIVE; ENDOCANNABINOID; ENZYME INHIBITOR; PIPERIDINE DERIVATIVE;

ANALGESIA; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; BRAIN; BROWN ADIPOSE TISSUE; CONTROLLED STUDY; DOSE TIME EFFECT RELATION; DRUG BRAIN LEVEL; DRUG PENETRATION; DRUG POTENCY; DRUG SPECIFICITY; FEMALE; HYPOACTIVITY; HYPOTHERMIA; LIVER; MALE; MOUSE; MUSCLE TISSUE; NONHUMAN; SPINAL CORD; SPLEEN; TETRAD TEST; TISSUE DISTRIBUTION; ANIMAL; ANTAGONISTS AND INHIBITORS; BRAIN CHEMISTRY; CHEMISTRY; DRUG EFFECTS; INFLAMMATION; METABOLISM; MOTOR ACTIVITY; NOCICEPTION; QUADRICEPS FEMORIS MUSCLE;

ADIPOSE TISSUE, BROWN; ANALGESICS; ANIMALS; ARACHIDONIC ACID; ARACHIDONIC ACIDS; BENZODIOXOLES; BRAIN CHEMISTRY; ENDOCANNABINOIDS; ENZYME INHIBITORS; FEMALE; GLYCERIDES; INFLAMMATION; LIVER; MALE; MICE; MONOACYLGLYCEROL LIPASES; MOTOR ACTIVITY; NOCICEPTION; PIPERIDINES; PROSTAGLANDINS; QUADRICEPS MUSCLE; SPINAL CORD; SPLEEN;

EID: 84921023711     PISSN: 00283908     EISSN: 18737064     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2014.12.001     Document Type: Article

References (40)

1. M. Alhouayek, and G.G. Muccioli COX-2-derived endocannabinoid metabolites as novel inflammatory mediators Trends Pharmacol. Sci. 35 2014 284 292
2. W.B. Anderson, M.J. Gould, R.D. Torres, V.A. Mitchell, and C.W. Vaughan Actions of the dual FAAH/MAGL inhibitor JZL195 in a murine inflammatory pain model Neuropharmacology 81 2014 224 230
3. J.L. Blankman, and B.F. Cravatt Chemical probes of endocannabinoid metabolism Pharmacol. Rev. 65 2013 849 871
4. J.L. Blankman, G.M. Simon, and B.F. Cravatt A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol Chem. Biol. 14 2007 1347 1356
5. J.W. Chang, M.J. Niphakis, K.M. Lum, A.B. Cognetta 3rd, C. Wang, M.L. Matthews, S. Niessen, M.W. Buczynski, L.H. Parsons, and B.F. Cravatt Highly selective inhibitors of monoacylglycerol lipase bearing a reactive group that is bioisosteric with endocannabinoid substrates Chem. Biol. 19 2012 579 588
6. F. Comelli, G. Giagnoni, I. Bettoni, M. Colleoni, and B. Costa 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
7. C. Consilvio, A.M. Vincent, and E.L. Feldman Neuroinflammation, COX-2, and ALS-a dual role? Exp. Neurol. 187 2004 1 10
8. M.S. Crowe, S.R. Nass, K.M. Gabella, and S.G. Kinsey The endocannabinoid system modulates stress, emotionality, and inflammation Brain, Behav. Immun. 42 2014 1 5
9. T.P. Dinh, D. Carpenter, F.M. Leslie, T.F. Freund, I. Katona, S.L. Sensi, S. Kathuria, and D. Piomelli Brain monoglyceride lipase participating in endocannabinoid inactivation Proc. Natl. Acad. Sci. 99 2002 10819 10824
10. S.G. Fagan, and V.A. Campbell The influence of cannabinoids on generic traits of neurodegeneration Br. J. Pharmacol. 171 2014 1347 1360
11. J. Fernandez-Ruiz, M.R. Pazos, M. Garcia-Arencibia, O. Sagredo, and J.A. Ramos Role of CB2 receptors in neuroprotective effects of cannabinoids Mol. Cell. Endocrinol. 286 2008 S91 S96
12. D. Fernández-Suárez, M. Celorrio, J.I. Riezu-Boj, A. Ugarte, R. Pacheco, H. González, J. Oyarzabal, C.J. Hillard, R. Franco, and M.S. Aymerich The monoacylglycerol lipase inhibitor JZL184 is neuroprotective and alters glial cell phenotype in the chronic MPTP mouse model Neurobiol. Aging 35 11 2014 2603 2616
13. J.R. Ghilardi, C.I. Svensson, S.D. Rogers, T.L. Yaksh, and P.W. Mantyh Constitutive spinal cyclooxygenase-2 participates in the initiation of tissue injury-induced hyperalgesia J. Neurosci. 24 2004 2727 2732
14. S. Ghosh, L.E. Wise, Y. Chen, R. Gujjar, A. Mahadevan, B.F. Cravatt, and A.H. Lichtman The monoacylglycerol lipase inhibitor JZL184 suppresses inflammatory pain in the mouse carrageenan model Life Sci. 92 2013 498 505
15. C.K. Glass, K. Saijo, B. Winner, M.C. Marchetto, and F.H. Gage Mechanisms underlying inflammation in neurodegeneration Cell 140 2010 918 934
16. B.M. Ignatowska-Jankowska, S. Ghosh, M.S. Crowe, S.G. Kinsey, M.J. Niphakis, R.A. Abdullah, Q. Tao, S.T. O' Neal, D.M. Walentiny, J.L. Wiley, B.F. Cravatt, and A.H. Lichtman In vivo characterization of the highly selective monoacylglycerol lipase inhibitor KML29: antinociceptive activity without cannabimimetic side effects Br. J. Pharmacol. 171 2014 1392 1407
17. M. Karlsson, J.A. Contreras, U. Hellman, H. Tornqvist, and C. Holm cDNA cloning, tissue distribution, and identification of the catalytic triad of monoglyceride lipase: evolutionary relationship to esterases, lysophospholipases, and haloperoxidases J. Biolog. Chem. 272 1997 27218 27223
18. M. Karlsson, K. Reue, Y.-R. Xia, A.J. Lusis, D. Langin, H. Tornqvist, and C. Holm Exon-intron organization and chromosomal localization of the mouse monoglyceride lipase gene Gene 272 2001 11 18
19. W.E. Kaufmann, P.F. Worley, J. Pegg, M. Bremer, and P. Isakson COX-2, a synaptically induced enzyme, is expressed by excitatory neurons at postsynaptic sites in rat cerebral cortex Proc. Natl. Acad. Sci. 93 1996 2317 2321
20. A.R. King, A. Duranti, A. Tontini, S. Rivara, A. Rosengarth, J.R. Clapper, G. Astarita, J.A. Geaga, H. Luecke, M. Mor, G. Tarzia, and D. Piomelli URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices Chem. Biol. 14 2007 1357 1365
21. J.Z. Long, W. Li, L. Booker, J.J. Burston, S.G. Kinsey, J.E. Schlosburg, F.J. Pavon, A.M. Serrano, D.E. Selley, L.H. Parsons, A.H. Lichtman, and B.F. Cravatt Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects Nat. Chem. Biol. 5 2009 37 44
22. J.Z. Long, D.K. Nomura, and B.F. Cravatt Characterization of monoacylglycerol lipase inhibition reveals differences in central and peripheral endocannabinoid metabolism Chem. Biol. 16 2009 744 753
23. J.Z. Long, D.K. Nomura, R.E. Vann, D.M. Walentiny, L. Booker, X. Jin, J.J. Burston, L.J. Sim-Selley, A.H. Lichtman, J.L. Wiley, and B.F. Cravatt 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
24. G. Marsicano, S. Goodenough, K. Monory, H. Hermann, M. Eder, A. Cannich, S.C. Azad, M.G. Cascio, S.O. Gutierrez, M. van der Stelt, M.L. Lopez-Rodriguez, E. Casanova, G. Schutz, W. Zieglgansberger, V. Di Marzo, C. Behl, and B. Lutz CB1 cannabinoid receptors and on-demand defense against excitotoxicity Science 302 2003 84 88
25. R. Mechoulam, and L.A. Parker The endocannabinoid system and the brain Annu Rev. Psychol. 64 2013 21 47
26. D.K. Nomura, B.E. Morrison, J.L. Blankman, J.Z. Long, S.G. Kinsey, M.C. Marcondes, A.M. Ward, Y.K. Hahn, A.H. Lichtman, B. Conti, and B.F. Cravatt Endocannabinoid hydrolysis generates brain prostaglandins that promote neuroinflammation Science 334 2011 809 813
27. P. Pacher, S. Batkai, and G. Kunos The endocannabinoid system as an emerging target of pharmacotherapy Pharmacol. Rev. 58 2006 389 462
28. R. Refinetti Daily activity patterns of a nocturnal and a diurnal rodent in a seminatural environment Physiol. Behav. 82 2004 285 294
29. C.A. Rouzer, and L.J. Marnett Cyclooxygenases: structural and functional insights J. Lipid Res. 50 Suppl. l 2009 S29 S34
30. E.L. Scotter, M.E. Abood, and M. Glass The endocannabinoid system as a target for the treatment of neurodegenerative disease Br. J. Pharmacol. 160 2010 480 498
31. C. Silvestri, and V. Di Marzo The endocannabinoid system in energy homeostasis and the etiopathology of metabolic disorders Cell. Metab. 17 2013 475 490
32. U. Taschler, F.P. Radner, C. Heier, R. Schreiber, M. Schweiger, G. Schoiswohl, K. Preiss-Landl, D. Jaeger, B. Reiter, H.C. Koefeler, J. Wojciechowski, C. Theussl, J.M. Penninger, A. Lass, G. Haemmerle, R. Zechner, and R. Zimmermann Monoglyceride lipase deficiency in mice impairs lipolysis and attenuates diet-induced insulin resistance J. Biol. Chem. 286 2011 17467 17477
33. P. Teismann COX-2 in the neurodegenerative process of Parkinson's disease Biofactors 38 2012 395 397
34. S. Valdeolivas, M.R. Pazos, T. Bisogno, F. Piscitelli, F.A. Iannotti, M. Allara, O. Sagredo, V. Di Marzo, and J. Fernandez-Ruiz The inhibition of 2-arachidonoyl-glycerol (2-AG) biosynthesis, rather than enhancing striatal damage, protects striatal neurons from malonate-induced death: a potential role of cyclooxygenase-2-dependent metabolism of 2-AG Cell. Death Dis. 4 2013 e862
35. M.J. van Bogaert, L. Groenink, R.S. Oosting, K.G. Westphal, J. van der Gugten, and B. Olivier Mouse strain differences in autonomic responses to stress Genes. Brain Behav. 5 2006 139 149
36. M. van der Stelt, S.H. Fox, M. Hill, A.R. Crossman, S. Petrosino, V. Di Marzo, and J.M. Brotchie 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 9 2005 1140 1142
37. S. Vandevoorde, K.O. Jonsson, G. Labar, E. Persson, D.M. Lambert, and C.J. Fowler Lack of selectivity of URB602 for 2-oleoylglycerol compared to anandamide hydrolysis in vitro Br. J. Pharmacol. 150 2007 186 191
38. P. Weydt, V.V. Pineda, A.E. Torrence, R.T. Libby, T.F. Satterfield, Eduardo R. Lazarowski, M.L. Gilbert, G.J. Morton, T.K. Bammler, A.D. Strand, L. Cui, R.P. Beyer, C.N. Easley, A.C. Smith, D. Krainc, S. Luquet, Ian R. Sweet, M.W. Schwartz, and A.R. La Spada Thermoregulatory and metabolic defects in Huntington's disease transgenic mice implicate PGC-1α in Huntington's disease neurodegeneration Cell. Metab. 4 2006 349 362
39. A. Witting, P. Weydt, S. Hong, M. Kliot, T. Moller, and N. Stella Endocannabinoids accumulate in spinal cord of SOD1 G93A transgenic mice J. Neurochem. 89 2004 1555 1557
40. Y. Yiangou, P. Facer, P. Durrenberger, I.P. Chessell, A. Naylor, C. Bountra, R.R. Banati, and P. Anand COX-2, CB2 and P2X7-immunoreactivities are increased in activated microglial cells/macrophages of multiple sclerosis and amyotrophic lateral sclerosis spinal cord BMC Neurol. 6 2006 12