Development and optimization of piperidyl-1,2,3-triazole ureas as selective chemical probes of endocannabinoid biosynthesis

Journal of Medicinal Chemistry

Volumn 56, Issue 21, 2013, Pages 8257-8269

  Hsu, Ku Lung ^a   Tsuboi, Katsunori ^a   Whitby, Landon R ^a   Speers, Anna E ^a   Pugh, Holly ^a   Inloes, Jordon ^a   Cravatt, Benjamin F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ENDOCANNABINOID; PIPERIDYL 1,2,3 TRIAZOLE UREA; UNCLASSIFIED DRUG;

ACTIVITY BASED PROTEIN PROFILING; ANALYTIC METHOD; ANIMAL TISSUE; ARTICLE; BIOTINYLATION; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IN VIVO STUDY; MASS SPECTROMETRY; MOLECULAR PROBE; MOUSE; NONHUMAN; PROTEOMICS; STRUCTURE ACTIVITY RELATION; TRANSIENT TRANSFECTION;

DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; ENDOCANNABINOIDS; ENZYME INHIBITORS; HUMANS; LIPOPROTEIN LIPASE; MOLECULAR STRUCTURE; PIPERIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; UREA;

EID: 84887960180     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400898x     Document Type: Article

References (30)

1. 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
2. Long, J. Z.; Cravatt, B. F. The metabolic serine hydrolases and their functions in mammalian physiology and disease Chem. Rev. 2011, 111, 6022-6063
3. Henness, S.; Perry, C. M. Orlistat: a review of its use in the management of obesity Drugs 2006, 66, 1625-1656
4. Thornberry, N. A.; Weber, A. E. Discovery of JANUVIA (Sitagliptin), a selective dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes Curr. Top. Med. Chem. 2007, 7, 557-568
5. Racchi, M.; Mazzucchelli, M.; Porrello, E.; Lanni, C.; Govoni, S. Acetylcholinesterase inhibitors: novel activities of old molecules Pharmacol. Res. 2004, 50, 441-451
6. Bachovchin, D. A.; Cravatt, B. F. The pharmacological landscape and therapeutic potential of serine hydrolases Nature Rev. Drug Discovery 2012, 11, 52-68
7. Bachovchin, D. A.; Mohr, J. T.; Speers, A. E.; Wang, C.; Berlin, J. M.; Spicer, T. P.; Fernandez-Vega, V.; Chase, P.; Hodder, P. S.; Schurer, S. C.; Nomura, D. K.; Rosen, H.; Fu, G. C.; Cravatt, B. F. Academic cross-fertilization by public screening yields a remarkable class of protein phosphatase methylesterase-1 inhibitors Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 6811-6816
8. Adibekian, A.; Martin, B. R.; Wang, C.; Hsu, K. L.; Bachovchin, D. A.; Niessen, S.; Hoover, H.; Cravatt, B. F. Click-generated triazole ureas as ultrapotent in vivo-active serine hydrolase inhibitors Nature Chem. Biol. 2011, 7, 469-478
9. Long, J. Z.; Li, W.; Booker, L.; Burston, J. J.; Kinsey, S. G.; Schlosburg, J. E.; Pavon, F. J.; Serrano, A. M.; Selley, D. E.; Parsons, L. H.; Lichtman, A. H.; Cravatt, B. F. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects Nature Chem. Biol. 2009, 5, 37-44
10. Chang, J. W.; Nomura, D. K.; Cravatt, B. F. A potent and selective inhibitor of KIAA1363/AADACL1 that impairs prostate cancer pathogenesis Chem. Biol. 2011, 18, 476-484
11. Ahn, K.; Smith, S. E.; Liimatta, M. B.; Beidler, D.; Sadagopan, N.; Dudley, D. T.; Young, T.; Wren, P.; Zhang, Y.; Swaney, S.; Van Becelaere, K.; Blankman, J. L.; Nomura, D. K.; Bhattachar, S. N.; Stiff, C.; Nomanbhoy, T. K.; Weerapana, E.; Johnson, D. S.; Cravatt, B. F. Mechanistic and pharmacological characterization of PF-04457845: a highly potent and selective fatty acid amide hydrolase inhibitor that reduces inflammatory and noninflammatory pain J. Pharmacol. Exp. Ther. 2011, 338, 114-124
12. Zuhl, A. M.; Mohr, J. T.; Bachovchin, D. A.; Niessen, S.; Hsu, K. L.; Berlin, J. M.; Dochnahl, M.; Lopez-Alberca, M. P.; Fu, G. C.; Cravatt, B. F. Competitive activity-based protein profiling identifies aza-beta-lactams as a versatile chemotype for serine hydrolase inhibition J. Am. Chem. Soc. 2012, 134, 5068-5071
13. 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 Nature Chem. Biol. 2012, 8, 999-1007
14. Hsu, K. L.; Tsuboi, K.; Speers, A. E.; Brown, S. J.; Spicer, T.; Fernandez-Vega, V.; Ferguson, J.; Cravatt, B. F.; Hodder, P.; Rosen, H. Optimization and characterization of a triazole urea inhibitor for diacylglycerol lipase beta (DAGL-β). In Probe Reports from the NIH Molecular Libraries Program [Internet]; National Center for Biotechnology Information: Bethesda, MD, 2012; (updated Feb 25 2013).
15. 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
16. 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
17. 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
18. Hsu, K. L.; Tsuboi, K.; Chang, J. W.; Whitby, L. R.; Speers, A. E.; Pugh, H.; Cravatt, B. F. Discovery and optimization of piperidyl-1,2,3-triazole ureas as potent, selective, and in vivo-active inhibitors of alpha/beta-hydrolase domain containing 6 (ABHD6). J. Med. Chem. 2013, DOI: 10.1021/jm400899c.
19. Jessani, N.; Liu, Y.; Humphrey, M.; Cravatt, B. F. Enzyme activity profiles of the secreted and membrane proteome that depict cancer cell invasiveness Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 10335-10340
20. Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Efficient Synthesis of 2-Substituted-1,2,3-triazoles Org. Lett. 2008, 10, 3171-3174
21. Nagano, J. M.; Hsu, K. L.; Whitby, L. R.; Niphakis, M. J.; Speers, A. E.; Brown, S. J.; Spicer, T.; Fernandez-Vega, V.; Ferguson, J.; Hodder, P.; Srinivasan, P.; Gonzalez, T. D.; Rosen, H.; Bahnson, B. J.; Cravatt, B. F. Selective inhibitors and tailored activity probes for lipoprotein-associated phospholipase A(2) Bioorg. Med. Chem. Lett. 2013, 23, 839-843
22. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
23. Speers, A. E.; Cravatt, B. F. Profiling enzyme activities in vivo using click chemistry methods Chem. Biol. 2004, 11, 535-546
24. Schuurs-Hoeijmakers, J. H.; Geraghty, M. T.; Kamsteeg, E. J.; Ben-Salem, S.; de Bot, S. T.; Nijhof, B.; van de Vondervoort, I. I. G. M.; van der Graaf, M.; Nobau, A. C.; Otte-Holler, I.; Vermeer, S.; Smith, A. C.; Humphreys, P.; Schwartzentruber, J.; Ali, B. R.; Al-Yahyaee, S. A.; Tariq, S.; Pramathan, T.; Bayoumi, R.; Kremer, H. P. H.; van de Warrenburg, B. P.; van den Akker, W. M.; Gilissen, C.; Veltman, J. A.; Janssen, I. M.; Vulto-van Silfhout, A. T.; van der Velde-Visser, S.; Lefeber, D. J.; Diekstra, A.; Erasmus, C. E.; Willemsen, M. A.; Vissers, L. E.; Lammens, M.; van Bokhoven, H.; Brunner, H. G.; Wevers, R. A.; Schenck, A.; Al-Gazali, L.; de Vries, B. B. A.; de Brouwer, A. P. M. Mutations in DDHD2, encoding an intracellular phospholipase A(1), cause a recessive form of complex hereditary spastic paraplegia Am. J. Hum. Genet. 2012, 91, 1073-1081
25. Nakajima, K.; Sonoda, H.; Mizoguchi, T.; Aoki, J.; Arai, H.; Nagahama, M.; Tagaya, M.; Tani, K. A novel phospholipase A1 with sequence homology to mammalian Sec23p-interacting protein, p125 J. Biol. Chem. 2002, 277, 11329-11335
26. Liu, Y.; Patricelli, M. P.; Cravatt, B. F. Activity-based protein profiling: the serine hydrolases Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 14694-14699
27. Kidd, D.; Liu, Y.; Cravatt, B. F. Profiling serine hydrolase activities in complex proteomes Biochemistry 2001, 40, 4005-4015
28. Bachovchin, D. A.; Ji, T.; Li, W.; Simon, G. M.; Blankman, J. L.; Adibekian, A.; Hoover, H.; Niessen, S.; Cravatt, B. F. Superfamily-wide portrait of serine hydrolase inhibition achieved by library-versus-library screening Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20941-20946
29. Jessani, N.; Niessen, S.; Wei, B. Q.; Nicolau, M.; Humphrey, M.; Ji, Y.; Han, W.; Noh, D. Y.; Yates, J. R., III; Jeffrey, S. S.; Cravatt, B. F. A streamlined platform for high-content functional proteomics of primary human specimens Nature Methods 2005, 2, 691-697
30. Speers, A. E.; Adam, G. C.; Cravatt, B. F. Activity-Based Protein Profiling in Vivo Using a Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition J. Am. Chem. Soc. 2003, 125, 4686-4687