Piperazine and piperidine triazole ureas as ultrapotent and highly selective inhibitors of monoacylglycerol lipase

Chemistry and Biology

Volumn 20, Issue 3, 2013, Pages 379-390

  Aaltonen, Niina ^a   Savinainen, Juha R ^a   Ribas, Casandra Riera ^a   Rönkkö, Jani ^a   Kuusisto, Anne ^a   Korhonen, Jani ^a   Navia Paldanius, Dina ^a   Häyrinen, Jukka ^a   Takabe, Piia ^a   Käsnänen, Heikki ^a   Pantsar, Tatu ^a   Laitinen, Tuomo ^a   Lehtonen, Marko ^a   Pasonen Seppänen, Sanna ^a   Poso, Antti ^a   Nevalainen, Tapio ^a   Laitinen, Jarmo T ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLGLYCEROL LIPASE; AKU 002; AKU 003; AKU 004; AKU 005; AKU 006; AKU 009; AKU 010; AKU 015; AKU 033; AKU 034; ESTERASE INHIBITOR; JJKK 006; JJKK 033; JJKK 046; JJKK 048; JZL 195; KML 29; PIPERAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; PROTEOME; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CANCER CELL; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG TARGETING; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; MELANOMA CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; SIGNAL TRANSDUCTION;

ANIMALS; ENZYME INHIBITORS; HEK293 CELLS; HUMANS; MICE; MONOACYLGLYCEROL LIPASES; PIPERAZINES; PIPERIDINES; RATS; SUBSTRATE SPECIFICITY; TRIAZOLES; UREA;

RODENTIA;

EID: 84875424144     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2013.01.012     Document Type: Article

References (40)

1. 1 receptor signalling in rat brain cryosections without affecting global LPA degradation BMC Pharmacol. 12 2012 7
2. T. Bertrand, F. Augé, J. Houtmann, A. Rak, F. Vallée, V. Mikol, P.F. Berne, N. Michot, D. Cheuret, C. Hoornaert, and M. Mathieu Structural basis for human monoglyceride lipase inhibition J. Mol. Biol. 396 2010 663 673
3. 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
4. A. Busquets-Garcia, E. Puighermanal, A. Pastor, R. de la Torre, R. Maldonado, and A. Ozaita Differential role of anandamide and 2-arachidonoylglycerol in memory and anxiety-like responses Biol. Psychiatry 70 2011 479 486
5. P.K. Chanda, Y. Gao, L. Mark, J. Btesh, B.W. Strassle, P. Lu, M.J. Piesla, M.Y. Zhang, B. Bingham, and A. Uveges Monoacylglycerol lipase activity is a critical modulator of the tone and integrity of the endocannabinoid system Mol. Pharmacol. 78 2010 996 1003
6. 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
7. R. Chen, J. Zhang, Y. Wu, D. Wang, G. Feng, Y.P. Tang, Z. Teng, and C. Chen Monoacylglycerol lipase is a therapeutic target for Alzheimer's disease Cell Rep. 2 2012 1329 1339
8. V. Di Marzo, T. Bisogno, and L. De Petrocellis Endocannabinoids and related compounds: walking back and forth between plant natural products and animal physiology Chem. Biol. 14 2007 741 756
9. M. Feledziak, D.M. Lambert, J. Marchand-Brynaert, and G.G. Muccioli Inhibitors of the endocannabinoid-degrading enzymes, or how to increase endocannabinoid's activity by preventing their hydrolysis Recent Patents CNS Drug Discov. 7 2012 49 70
10. C.J. Fowler Monoacylglycerol lipase - a target for drug development? Br. J. Pharmacol. 166 2012 1568 1585
11. A. Holtfrerich, T. Makharadze, and M. Lehr High-performance liquid chromatography assay with fluorescence detection for the evaluation of inhibitors against human recombinant monoacylglycerol lipase Anal. Biochem. 399 2010 218 224
12. M. Kano, T. Ohno-Shosaku, Y. Hashimotodani, M. Uchigashima, and M. Watanabe Endocannabinoid-mediated control of synaptic transmission Physiol. Rev. 89 2009 309 380
13. 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. Biol. Chem. 272 1997 27218 27223
14. A.R. King, E.Y. Dotsey, A. Lodola, K.M. Jung, A. Ghomian, Y. Qiu, J. Fu, M. Mor, and D. Piomelli Discovery of potent and reversible monoacylglycerol lipase inhibitors Chem. Biol. 16 2009 1045 1052
15. G. Labar, J. Wouters, and D.M. Lambert A review on the monoacylglycerol lipase: at the interface between fat and endocannabinoid signalling Curr. Med. Chem. 17 2010 2588 2607
16. M. Lehtonen, M. Storvik, H. Malinen, P. Hyytiä, M. Lakso, S. Auriola, G. Wong, and J.C. Callaway Determination of endocannabinoids in nematodes and human brain tissue by liquid chromatography electrospray ionization tandem mass spectrometry J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 879 2011 677 694
17. W. Li, J.L. Blankman, and B.F. Cravatt A functional proteomic strategy to discover inhibitors for uncharacterized hydrolases J. Am. Chem. Soc. 129 2007 9594 9595
18. J.Z. Long, W. Li, L. Booker, J.J. Burston, S.G. Kinsey, J.E. Schlosburg, F.J. Pavón, A.M. Serrano, D.E. Selley, and L.H. Parsons Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects Nat. Chem. Biol. 5 2009 37 44
19. 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. USA 106 2009 20270 20275
20. A. Minkkilä, S. Saario, and T. Nevalainen Discovery and development of endocannabinoid-hydrolyzing enzyme inhibitors Curr. Top. Med. Chem. 10 2010 828 858
21. L. Morera, G. Labar, G. Ortar, and D.M. Lambert Development and characterization of endocannabinoid hydrolases FAAH and MAGL inhibitors bearing a benzotriazol-1-yl carboxamide scaffold Bioorg. Med. Chem. 20 2012 6260 6275
22. M.M. Mulvihill, and D.K. Nomura Therapeutic potential of monoacylglycerol lipase inhibitors Life Sci. 2012 10.1016/j.lfs.2012.10.025 Published online November 8, 2012
23. D. Navia-Paldanius, J.R. Savinainen, and J.T. Laitinen Biochemical and pharmacological characterization of human α/β-hydrolase domain containing 6 (ABHD6) and 12 (ABHD12) J. Lipid Res. 53 2012 2413 2424
24. D.K. Nomura, J.L. Blankman, G.M. Simon, K. Fujioka, R.S. Issa, A.M. Ward, B.F. Cravatt, and J.E. Casida Activation of the endocannabinoid system by organophosphorus nerve agents Nat. Chem. Biol. 4 2008 373 378
25. D.K. Nomura, J.Z. Long, S. Niessen, H.S. Hoover, S.W. Ng, and B.F. Cravatt Monoacylglycerol lipase regulates a fatty acid network that promotes cancer pathogenesis Cell 140 2010 49 61
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. V.A. Palomäki, M. Lehtonen, J.R. Savinainen, and J.T. Laitinen Visualization of 2-arachidonoylglycerol accumulation and cannabinoid CB1 receptor activity in rat brain cryosections by functional autoradiography J. Neurochem. 101 2007 972 981
28. A. Petronelli, G. Pannitteri, and U. Testa Triterpenoids as new promising anticancer drugs Anticancer Drugs 20 2009 880 892
29. J.R. Piro, D.I. Benjamin, J.M. Duerr, Y. Pi, C. Gonzales, K.M. Wood, J.W. Schwartz, D.K. Nomura, and T.A. Samad A dysregulated endocannabinoid-eicosanoid network supports pathogenesis in a mouse model of Alzheimer's disease Cell Rep. 1 2012 617 623
30. S.M. Saario, and J.T. Laitinen Therapeutic potential of endocannabinoid-hydrolysing enzyme inhibitors Basic Clin. Pharmacol. Toxicol. 101 2007 287 293
31. S.M. Saario, J.R. Savinainen, J.T. Laitinen, T. Järvinen, and R. Niemi Monoglyceride lipase-like enzymatic activity is responsible for hydrolysis of 2-arachidonoylglycerol in rat cerebellar membranes Biochem. Pharmacol. 67 2004 1381 1387
32. S.M. Saario, O.M. Salo, T. Nevalainen, A. Poso, J.T. Laitinen, T. Järvinen, and R. Niemi Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes Chem. Biol. 12 2005 649 656
33. S.M. Saario, A. Poso, R.O. Juvonen, T. Järvinen, and O.M. Salo-Ahen Fatty acid amide hydrolase inhibitors from virtual screening of the endocannabinoid system J. Med. Chem. 49 2006 4650 4656
34. J.R. Savinainen, M. Yoshino, A. Minkkilä, T. Nevalainen, and J.T. Laitinen Characterization of binding properties of monoglyceride lipase inhibitors by a versatile fluorescence-based technique Anal. Biochem. 399 2010 132 134
35. J.R. Savinainen, S.M. Saario, and J.T. Laitinen The serine hydrolases MAGL, ABHD6 and ABHD12 as guardians of 2-arachidonoylglycerol signalling through cannabinoid receptors Acta Physiol. (Oxf.) 204 2012 267 276
36. C. Schalk-Hihi, C. Schubert, R. Alexander, S. Bayoumy, J.C. Clemente, I. Deckman, R.L. DesJarlais, K.C. Dzordzorme, C.M. Flores, and B. Grasberger Crystal structure of a soluble form of human monoglyceride lipase in complex with an inhibitor at 1.35 Å resolution Protein Sci. 20 2011 670 683
37. J.E. Schlosburg, J.L. Blankman, J.Z. Long, D.K. Nomura, B. Pan, S.G. Kinsey, P.T. Nguyen, D. Ramesh, L. Booker, and J.J. Burston Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system Nat. Neurosci. 13 2010 1113 1119
38. U. Taschler, F.P. Radner, C. Heier, R. Schreiber, M. Schweiger, G. Schoiswohl, K. Preiss-Landl, D. Jaeger, B. Reiter, and H.C. Koefeler Monoglyceride lipase deficiency in mice impairs lipolysis and attenuates diet-induced insulin resistance J. Biol. Chem. 286 2011 17467 17477
39. F. Tchantchou, and Y. Zhang Selective inhibition of α/β- hydrolase domain 6 attenuates neurodegeneration, alleviates blood brain barrier breakdown and improves functional recovery in a mouse model of traumatic brain injury J. Neurotrauma 2012 10.1089/neu.2012.2647 Published online November 14, 2012
40. R. Zechner, R. Zimmermann, T.O. Eichmann, S.D. Kohlwein, G. Haemmerle, A. Lass, and F. Madeo FAT SIGNALS - lipases and lipolysis in lipid metabolism and signaling Cell Metab. 15 2012 279 291