Discovery of glycine sulfonamides as dual inhibitors of sn-1-diacylglycerol lipase α and α/β-hydrolase domain 6

Journal of Medicinal Chemistry

Volumn 57, Issue 15, 2014, Pages 6610-6622

  Janssen, Freek J ^a   Deng, Hui ^a   Baggelaar, Marc P ^a   Allarà, Marco ^b   Van Der Wel, Tom ^a   Den Dulk, Hans ^a   Ligresti, Alessia ^b   Van Esbroeck, Annelot C M ^a   McGuire, Ross ^c   Di Marzo, Vincenzo ^b   Overkleeft, Herman S ^a   Van Der Stelt, Mario ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b Endocannabinoid Research Group   (Italy)

^c BioAxis Research   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANTILIPEMIC AGENT; CARBOXYLIC ACID; GLYCINE SULFONAMIDE INHIBITOR; HYDROLASE; LIPOPROTEIN LIPASE; MOLECULAR THERAPY AGENT; SN 1 LIPOPROTEIN LIPASE ALPHA; SULFONAMIDE; UNCLASSIFIED DRUG; ABHD6 PROTEIN, HUMAN; ABHD6 PROTEIN, MOUSE; ACYLGLYCEROL LIPASE; GLYCINE; N-((2,2-DIMETHYLCHROMAN-6-YL)SULFONYL)-N-(4-PHENOXYBENZYL)GLYCINE; PROTEOME;

ARTICLE; BRAIN MEMBRANE; EMBRYO; HUMAN; HUMAN CELL; METABOLIC SYNDROME X; MOLECULAR THERAPY; OBESITY; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; ANIMAL; ANTAGONISTS AND INHIBITORS; BRAIN; CHEMICAL STRUCTURE; CHEMISTRY; HEK293 CELL LINE; METABOLISM; MOUSE;

ANIMALS; BRAIN; GLYCINE; HEK293 CELLS; HUMANS; LIPOPROTEIN LIPASE; MICE; MODELS, MOLECULAR; MONOACYLGLYCEROL LIPASES; PROTEOME; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84906091270     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500681z     Document Type: Article

References (31)

1. Katona, I.; Freund, T. F. Multiple functions of endocannabinoid signaling in the brain Annu. Rev. Neurosci. 2012, 35, 529-558
2. Gao, Y.; Vasilyev, D. V.; Goncalves, M. B.; Howell, F. V.; Hobbs, C.; Reisenberg, M.; Shen, R.; Zhang, M. Y.; Strassle, B. W.; Lu, P.; Mark, L.; Piesla, M. J.; Deng, K.; Kouranova, E. V.; Ring, R. H.; Whiteside, G. T.; Bates, B.; Walsh, F. S.; Williams, G.; Pangalos, M. N.; Samad, T. A.; Doherty, P. Loss of retrograde endocannabinoid signaling and reduced adult neurogenesis in diacylglycerol lipase knock-out mice J. Neurosci. 2010, 30, 2017-2024
3. Tanimura, A.; Yamazaki, M.; Hashimotodani, Y.; Uchigashima, M.; Kawata, S.; Abe, M.; Kita, Y.; Hashimoto, K.; Shimizu, T.; Watanabe, M.; Sakimura, K.; Kano, M. The endocannabinoid 2-arachidonoylglycerol produced by diacylglycerol lipase alpha mediates retrograde suppression of synaptic transmission Neuron 2010, 65, 320-327
4. Mackie, K. Cannabinoid receptors as therapeutic targets Annu. Rev. Pharmacol. Toxicol. 2006, 46, 101-122
5. Nomura, D. K.; Morrison, B. E.; Blankman, J. L.; Long, J. Z.; Kinsey, S. G.; Marcondes, M. C.; Ward, A. M.; Hahn, Y. K.; Lichtman, A. H.; Conti, B.; Cravatt, B. F. Endocannabinoid hydrolysis generates brain prostaglandins that promote neuroinflammation Science 2011, 334, 809-813
6. Valdeolivas, S.; Pazos, M. R.; Bisogno, T.; Piscitelli, F.; Iannotti, F. A.; Allara, M.; Sagredo, O.; Di Marzo, V.; Fernandez-Ruiz, J. 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. 2013, 4, 862
7. Alhouayek, M.; Masquelier, J.; Cani, P. D.; Lambert, D. M.; Muccioli, G. G. Implication of the anti-inflammatory bioactive lipid prostaglandin D2-glycerol ester in the control of macrophage activation and inflammation by ABHD6 Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 17558-17563
8. Di Marzo, V. Targeting the endocannabinoid system: to enhance or reduce? Nat. Rev. Drug Discovery 2008, 7, 438-455
9. Kohnz, R. A.; Nomura, D. K. Chemical approaches to therapeutically target the metabolism and signaling of the endocannabinoid 2-AG and eicosanoids. Chem. Soc. Rev. [Online early access]. Published Online: Mar 28, 2014.
10. Bisogno, T.; Howell, F.; Williams, G.; Minassi, A.; Cascio, M. G.; Ligresti, A.; Matias, I.; Schiano-Moriello, A.; Paul, P.; Williams, E. J.; Gangadharan, U.; Hobbs, C.; Di Marzo, V.; Doherty, P. Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain J. Cell Biol. 2003, 163, 463-468
11. Baggelaar, M. P.; Janssen, F. J.; van Esbroeck, A. C.; den Dulk, H.; Allara, M.; Hoogendoorn, S.; McGuire, R.; Florea, B. I.; Meeuwenoord, N.; van den Elst, H.; van der Marel, G. A.; Brouwer, J.; Di Marzo, V.; Overkleeft, H. S.; van der Stelt, M. Development of an activity-based probe and in silico design reveal highly selective inhibitors for diacylglycerol lipase-alpha in brain Angew. Chem., Int. Ed. 2013, 52, 12081-12085
12. Bisogno, T.; Cascio, M. G.; Saha, B.; Mahadevan, A.; Urbani, P.; Minassi, A.; Appendino, G.; Saturnino, C.; Martin, B.; Razdan, R.; Di Marzo, V. Development of the first potent and specific inhibitors of endocannabinoid biosynthesis Biochim. Biophys. Acta 2006, 1761, 205-212
13. Bisogno, T.; Burston, J. J.; Rai, R.; Allara, M.; Saha, B.; Mahadevan, A.; Razdan, R. K.; Wiley, J. L.; Di Marzo, V. Synthesis and pharmacological activity of a potent inhibitor of the biosynthesis of the endocannabinoid 2-arachidonoylglycerol ChemMedChem 2009, 4, 946-950
14. Bisogno, T.; Mahadevan, A.; Coccurello, R.; Chang, J. W.; Allara, M.; Chen, Y.; Giacovazzo, G.; Lichtman, A.; Cravatt, B.; Moles, A.; Di Marzo, V. A novel fluorophosphonate inhibitor of the biosynthesis of the endocannabinoid 2-arachidonoylglycerol with potential anti-obesity effects Br. J. Pharmacol. 2013, 169, 784-793
15. Ortar, G.; Bisogno, T.; Ligresti, A.; Morera, E.; Nalli, M.; Di Marzo, V. Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism J. Med. Chem. 2008, 51, 6970-6979
16. Hsu, K. L.; Tsuboi, K.; Adibekian, A.; Pugh, H.; Masuda, K.; Cravatt, B. F. DAGLbeta inhibition perturbs a lipid network involved in macrophage inflammatory responses Nat. Chem. Biol. 2012, 8, 999-1007
17. Thomas, G.; Betters, J. L.; Lord, C. C.; Brown, A. L.; Marshall, S.; Ferguson, D.; Sawyer, J.; Davis, M. A.; Melchior, J. T.; Blume, L. C.; Howlett, A. C.; Ivanova, P. T.; Milne, S. B.; Myers, D. S.; Mrak, I.; Leber, V.; Heier, C.; Taschler, U.; Blankman, J. L.; Cravatt, B. F.; Lee, R. G.; Crooke, R. M.; Graham, M. J.; Zimmermann, R.; Brown, H. A.; Brown, J. M. The serine hydrolase ABHD6 is a critical regulator of the metabolic syndrome Cell Rep. 2013, 5, 508-520
18. Long, J. Z.; Cravatt, B. F. The metabolic serine hydrolases and their functions in mammalian physiology and disease Chem. Rev. 2011, 111, 6022-6063
19. Simon, G. M.; Cravatt, B. F. Activity-based proteomics of enzyme superfamilies: serine hydrolases as a case study J. Biol. Chem. 2010, 285, 11051-11055
20. Appiah, K. K.; Blat, Y.; Robertson, B. J.; Pearce, B. C.; Pedicord, D. L.; Gentles, R. G.; Yu, X. C.; Mseeh, F.; Nguyen, N.; Swaffield, J. C.; Harden, D. G.; Westphal, R. S.; Banks, M. N.; O'Connell, J. C. Identification of small molecules that selectively inhibit diacylglycerol lipase-alpha activity J. Biomol. Screening 2014, 19, 595-605
21. Chupak, L. S.; Zheng, X.; Ding, M.; Hu, S.; Huang, Y.; Gentles, R. G. Glycine chroman-6-sulfonamides for use as inhibitors of diacylglycerol lipase. US 20110207749 A1, 2011.
22. Johnson, D. S.; Stiff, C.; Lazerwith, S. E.; Kesten, S. R.; Fay, L. K.; Morris, M.; Beidler, D.; Liimatta, M. B.; Smith, S. E.; Dudley, D. T.; Sadagopan, N.; Bhattachar, S. N.; Kesten, S. J.; Nomanbhoy, T. K.; Cravatt, B. F.; Ahn, K. Discovery of PF-04457845: a highly potent, orally bioavailable, and selective urea FAAH Inhibitor ACS Med. Chem. Lett. 2011, 2, 91-96
23. Pedicord, D. L.; Flynn, M. J.; Fanslau, C.; Miranda, M.; Hunihan, L.; Robertson, B. J.; Pearce, B. C.; Yu, X. C.; Westphal, R. S.; Blat, Y. Molecular characterization and identification of surrogate substrates for diacylglycerol lipase alpha Biochem. Biophys. Res. Commun. 2011, 411, 809-814
24. Chang, J. W.; Cognetta, A. B., 3rd; Niphakis, M. J.; Cravatt, B. F. Proteome-wide reactivity profiling identifies diverse carbamate chemotypes tuned for serine hydrolase inhibition ACS Chem. Biol. 2013, 8, 1590-1599
25. Krieger, E.; Koraimann, G.; Vriend, G. Increasing the precision of comparative models with YASARA NOVA a self-parameterizing force field Proteins 2002, 47, 393-402
26. Trott, O.; Olson, A. J. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 2010, 31, 455-461
27. Navia-Paldanius, D.; Savinainen, J. R.; Laitinen, J. T. Biochemical and pharmacological characterization of human alpha/beta-hydrolase domain containing 6 (ABHD6) and 12 (ABHD12) J. Lipid Res. 2012, 53, 2413-2424
28. Matias, I.; Di Marzo, V. Endocannabinoids and the control of energy balance Trends Endocrinol. Metab. 2007, 18, 27-37
29. Kirkham, T. C. Endocannabinoids and the non-homeostatic control of appetite Curr. Top. Behav. Neurosci. 2009, 1, 231-253
30. Dou, D.; Mandadapu, S. R.; Alliston, K. R.; Kim, Y.; Chang, K. O.; Groutas, W. C. Design and synthesis of inhibitors of noroviruses by scaffold hopping Bioorg. Med. Chem. 2011, 19, 5749-5755
31. Kharul, R.; Bhuniya, D.; Mookhtiar, K. A.; Singu, U.; Hazare, A.; Patil, S.; Datrange, L.; Thakkar, M. Amide compounds, compositions and applications thereof. WO 2013042139 A1, 2013.