Identification and characterization of a new reversible MAGL inhibitor

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 13, 2014, Pages 3285-3291

  Tuccinardi, Tiziano ^a   Granchi, Carlotta ^a   Rizzolio, Flavio ^b   Caligiuri, Isabella ^b   Battistello, Vittoria ^a   Toffoli, Giuseppe ^b   Minutolo, Filippo ^a   Macchia, Marco ^a   Martinelli, Adriano ^a  

^a UNIVERSITY OF PISA   (Italy)

^b CENTRO DI RIFERIMENTO ONCOLOGICO   (Italy)

Author keywords

Hydrolase; MAGL; Monoacylglycerol lipase inhibitors; Virtual screening

Indexed keywords

ASN 04370655; ASN 04450196; ASN 04450205; ASN 06583334; ASN 08951882; ASN 15424931; BAS 02374392; BAS 04840801; BAS 07123797; CAY 10499; ESTERASE INHIBITOR; MONOACYLGLYCEROL LIPASE INHIBITOR; UNCLASSIFIED DRUG; [4 (4 CHLOROBENZOYL)PIPERIDIN 1 YL](4 METHOXYPHENYL)METHANONE; ACYLGLYCEROL LIPASE; ANTINEOPLASTIC AGENT; ENZYME INHIBITOR;

ARTICLE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG SCREENING; DRUG STRUCTURE; HUMAN; HUMAN CELL; MOLECULAR DOCKING; MOLECULAR DYNAMICS; PHYSICAL CHEMISTRY; ANTAGONISTS AND INHIBITORS; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; MCF 7 CELL LINE; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; HUMANS; MCF-7 CELLS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOACYLGLYCEROL LIPASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84901944199     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.04.057     Document Type: Article

References (35)

1. M.M. Mulvihill, and D.K. Nomura Life Sci. 92 2013 492
2. T.P. Dinh, D. Carpenter, F.M. Leslie, T.F. Freund, I. Katona, S.L. Sensi, S. Kathuria, and D. Piomelli Proc. Natl. Acad. Sci. U.S.A. 99 2002 10819
3. W. Gonsiorek, C. Lunn, X. Fan, S. Narula, D. Lundell, and R.W. Hipkin Mol. Pharmacol. 57 2000 1045
4. 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 Science 334 2011 809
5. J. Guindon, A. Guijarro, D. Piomelli, and A.G. Hohmann Br. J. Pharmacol. 163 2011 1464
6. R. Chen, J. Zhang, Y. Wu, D. Wang, G. Feng, Y.P. Tang, Z. Teng, and C. Chen Cell Rep. 2 2012 1329
7. D.K. Nomura, J.Z. Long, S. Niessen, H.S. Hoover, S.W. Ng, and B.F. Cravatt Cell 140 2010 49
8. L. Ye, B. Zhang, E.G. Seviour, K.X. Tao, X.H. Liu, Y. Ling, J.Y. Chen, and G.B. Wang Cancer. Lett. 307 2011 6
9. D.K. Nomura, D.P. Lombardi, J.W. Chang, S. Niessen, A.M. Ward, J.Z. Long, H.H. Hoover, and B.F. Cravatt Chem. Biol. 18 2011 846
10. G.G. Muccioli, G. Labar, and D.M. Lambert ChemBioChem 9 2008 2704
11. N. Zvonok, L. Pandarinathan, J. Williams, M. Johnston, I. Karageorgos, D.R. Janero, S.C. Krishnan, and A. Makriyannis Chem. Biol. 15 2008 854
12. A.R. King, A. Lodola, C. Carmi, J. Fu, M. Mor, and D. Piomelli Br. J. Pharmacol. 157 2009 974
13. 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 Nat. Chem. Biol. 5 2009 37
14. N. Matuszak, G.G. Muccioli, G. Labar, and D.M. Lambert J. Med. Chem. 52 2009 7410
15. C.N. Kapanda, J. Masquelier, G. Labar, G.G. Muccioli, J.H. Poupaert, and D.M. Lambert J. Med. Chem. 55 2012 5774
16. J.E. Schlosburg, J.L. Blankman, J.Z. Long, D.K. Nomura, B. Pan, S.G. Kinsey, P.T. Nguyen, D. Ramesh, L. Booker, J.J. Burston, E.A. Thomas, D.E. Selley, L.J. Sim-Selley, Q.S. Liu, A.H. Lichtman, and B.F. Cravatt Nat. Neurosci. 13 2010 1113
17. A.R. King, E.Y. Dotsey, A. Lodola, K.M. Jung, A. Ghomian, Y. Qiu, J. Fu, M. Mor, and D. Piomelli Chem. Biol. 16 2009 1045
18. C. Schalk-Hihi, C. Schubert, R. Alexander, S. Bayoumy, J.C. Clemente, I. Deckman, R.L. DesJarlais, K.C. Dzordzorme, C.M. Flores, B. Grasberger, J.K. Kranz, F. Lewandowski, L. Liu, H. Ma, D. Maguire, M.J. Macielag, M.E. McDonnell, T. Mezzasalma Haarlander, R. Miller, C. Milligan, C. Reynolds, and L.C. Kuo Protein Sci. 20 2011 670
19. J.A. Cisneros, E. Bjorklund, I. Gonzalez-Gil, Y. Hu, A. Canales, F.J. Medrano, A. Romero, S. Ortega-Gutierrez, C.J. Fowler, and M.L. Lopez-Rodriguez J. Med. Chem. 55 2012 824
20. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucleic Acids Res. 28 2000 235
21. OMEGA, version 2.4.6. OpenEye Scientific Software Inc, Santa Fe, NM, USA, www.eyesopen.com, 2013.
22. ROCS, version 3.1.2. OpenEye Scientific Software Inc, Santa Fe, NM, USA, www.eyesopen.com, 2013.
23. D.R. Houston, and M.D. Walkinshaw J. Chem. Inf. Model. 53 2013 384
24. T. Cheng, X. Li, Y. Li, Z. Liu, and R. Wang J. Chem. Inf. Model. 49 2009 1079
25. M.W. Chang, C. Ayeni, S. Breuer, and B.E. Torbett PLoS ONE 5 2010 e11955
26. A. Kukol Eur. J. Med. Chem. 46 2011 4661
27. DOCK, version 6.0. Molecular Design Institute, University of California: San Francisco, CA, 1998.
28. M.L. Verdonk, J.C. Cole, M.J. Hartshorn, C.W. Murray, and R.D. Taylor Proteins 52 2003 609
29. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, and A.J. Olson J. Comput. Chem. 30 2009 2785
30. FRED, version 3.0.0. OpenEye Scientific Software Inc, Santa Fe, NM, USA, www.eyesopen.com, 2013.
31. X. Wang, K. Sarris, K. Kage, D. Zhang, S.P. Brown, T. Kolasa, C. Surowy, O.F. El Kouhen, S.W. Muchmore, J.D. Brioni, and A.O. Stewart J. Med. Chem. 52 2009 170
32. R.A. Copeland Methods Biochem. Anal. 46 2005 1
33. T. Tuccinardi, M. Botta, A. Giordano, and A. Martinelli J. Chem. Inf. Model. 50 2010 1432
34. Case, D. A.; Darden, T. A.; III, T. E. C.; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Walker, R. C.; Zhang, W.; Merz, K. M.; Roberts, B.; Wang, B.; Hayik, S.; Roitberg, A.; Seabra, G.; Kolossváry, I.; Wong, K. F.; Paesani, F.; Vanicek, J.; Liu, J.; Wu, X.; Brozell, S. R.; Steinbrecher, T.; Gohlke, H.; Cai, Q.; Ye, X.; Wang, J.; Hsieh, M.-J.; Cui, G.; Roe, D. R.; Mathews, D. H.; Seetin, M. G.; Sagui, C.; Babin, V.; Luchko, T.; Gusarov, S.; Kovalenko, A.; Kollman, P. A.: University of California: San Francisco, CA, 2010.
35. Asinex. http://www.asinex.com/index.html.