Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 1, 2015, Pages 241-263

  Gianella Borradori, Matteo ^a   Christou, Ivy ^b   Bataille, Carole J R ^a   Cross, Rebecca L ^a   Wynne, Graham M ^a   Greaves, David R ^b   Russell, Angela J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Agonist; Cannabinoid receptor 1; Cannabinoid receptor 2; Inflammation; Ligand based screening

Indexed keywords

4 [4 (1,1 DIMETHYLHEPTYL) 2,6 DIMETHOXYPHENYL] 6,6 DIMETHYLBICYCLO[3.1.1]HEPT 2 EN 2 YLMETHANOL; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID 2 RECEPTOR AGONIST; G PROTEIN COUPLED RECEPTOR; PROTEIN KINASE; ANTIINFLAMMATORY AGENT; CANNABINOID RECEPTOR AGONIST; LIGAND; MOLECULAR LIBRARY;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHO CELL LINE; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG ABSORPTION; DRUG IDENTIFICATION; DRUG SCREENING; DRUG SELECTIVITY; DRUG STABILITY; DRUG STRUCTURE; IN VITRO STUDY; MEDICINAL CHEMISTRY; NONHUMAN; RECEPTOR BINDING; RECEPTOR UPREGULATION; STRUCTURE ACTIVITY RELATION; AGONISTS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; MOLECULAR LIBRARY; PHARMACOLOGY; PROCEDURES;

ANTI-INFLAMMATORY AGENTS; CANNABINOID RECEPTOR AGONISTS; DRUG EVALUATION, PRECLINICAL; KINETICS; LIGANDS; MODELS, MOLECULAR; RECEPTOR, CANNABINOID, CB2; SMALL MOLECULE LIBRARIES;

EID: 84918793359     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.11.002     Document Type: Article

References (90)

1. S. Galiegue, S. Mary, J. Marchand, D. Dussossoy, D. Carriere, P. Carayon, M. Bouaboula, D. Shire, G. Le Fur, and P. Casellas Eur. J. Biochem. 232 1995 54
2. S. Munro, K.L. Thomas, and M. Abu-Shaar Nature 365 1993 61
3. E. Núñez, C. Benito, M.R. Pazos, A. Barbachano, O. Fajardo, S. González, R.M. Tolón, and J. Romero Synapse 53 2004 208
4. M.D. Van Sickle, M. Duncan, P.J. Kingsley, A. Mouihate, P. Urbani, K. Mackie, N. Stella, A. Makriyannis, D. Piomelli, J.S. Davison, L.J. Marnett, V. Di Marzo, Q.J. Pittman, K.D. Patel, and K.A. Sharkey Science 310 2005 329
5. U. Anand, W.R. Otto, D. Sanchez-Herrera, P. Facer, Y. Yiangou, Y. Korchev, R. Birch, C. Benham, C. Bountra, I.P. Chessell, and P. Anand Pain 138 2008 667
6. G. Wotherspoon, A. Fox, P. McIntyre, S. Colley, S. Bevan, and J. Winter Neuroscience 135 2005 235
7. G.T. Whiteside, G.P. Lee, and K.J. Valenzano Curr. Med. Chem. 14 2007 917
8. For a recent review see: M. Beltrano Mini Rev. Med. Chem. 9 2009 11
9. D.M. Slipetz, G.P. O'Neill, L. Favreau, C. Dufresne, M. Gallant, Y. Gareau, D. Guay, M. Labelle, and K.M. Metters Mol. Pharmacol. 48 1995 352
10. M. Bouaboula, C. Poinot-Chazel, J. Marchand, X. Canat, B. Bourrié, M. Rinaldi-Carmona, B. Calandra, G. Le Fur, and P. Casellas Eur. J. Biochem. 237 1996 704
11. S. Han, J. Thalte, and R.M. Jones Ann. Rep. Med. Chem. 44 2009 227
12. S. Han, J. Thatte, D.J. Buzard, and R.M. Jones J. Med. Chem. 56 2013 8224
13. Y. Gaoni, and R. Mechoulam J. Am. Chem. Soc. 86 1964 1646
14. for a recent review see: S.H. Burstein Bioorg. Med. Chem. 22 2014 2830
15. V. Di Marzo, and L. De Petrocellis Annu. Rev. Med. 57 2006 553
16. J.S. Berman, C. Symonds, and R. Birch Pain 112 2004 299
17. D.T. Wade, P. Makela, P. Robson, H. House, and C. Bateman Mult. Scler. 10 2004 434
18. For a recent reviews see: (a) K. Worm, and R.E. Dolle Curr. Pharm. Des. 15 2009 3345
19. K.D. Patel, J.S. Davison, Q.J. Pittman, and K.A. Sharkey Curr. Med. Chem. 17 2010 1394
20. A. Tourteau, N. Leleu-Chavain, M. Body-Malapel, V. Andrzejak, A. Barczyk, M. Djouina, B. Rigo, P. Desreumaux, P. Chavatte, and R. Millet Bioorg. Med. Chem. Lett. 24 2014 1322
21. A. Weissman, G.M. Milne, and L.S. Melvin J. Pharmacol. Exp. Ther. 223 1982 516
22. L. Hanuš, A. Breuer, S. Tchilibon, S. Shiloah, D. Goldenberg, M. Horowitz, R.G. Pertwee, R.A. Ross, R. Mechoulam, and E. Fride Proc. Natl. Acad. Sci. U.S.A. 96 1999 14228
23. X.Q. Xie, J.Z. Chen, and E.M. Billings Proteins-Struct. Funct. Genet. 53 2003 307
24. O.M.H. Salo, K.H. Raitio, J.R. Savinainen, T. Nevalainen, M. Lahtela-Kakkonen, J.T.T. Laitinen, T. Järvinen, and A. Poso J. Med. Chem. 48 2005 7166
25. N. Renault, X. Laurent, A. Farce, J. El Bakali, R. Mansouri, P. Gervois, R. Millet, P. Desreumaux, C. Furman, and P. Chavatte Chem. Biol. Drug Des. 81 2013 442
26. P. Markt, C. Feldmann, J.M. Rollinger, S. Raduner, D. Schuster, J. Kirchmair, S. Distinto, G.M. Spitzer, G. Wolber, C. Laggner, K.-H. Altmann, T. Langer, and J. Gertsch J. Med. Chem. 52 2009 369
27. S.P. Hollinshead, M.W. Tidwell, J. Palmer, R. Guidetti, A. Sanderson, M.P. Johnson, M.G. Chambers, J. Oskins, R. Stratford, and P.C. Astles J. Med. Chem. 56 2013 5722
28. M. Rinaldi-Carmona, F. Barth, J. Millan, J.-M. Derocq, P. Casellas, C. Congy, D. Oustric, M. Sarran, M. Bouaboula, B. Calandra, M. Portier, D. Shire, J.-C. Brelière, and G.L. Fur J. Pharmacol. Exp. Ther. 284 1998 644
29. Y. Hosohata, R.M. Quock, K. Hosohata, A. Makriyannis, P. Consroe, W.R. Roeske, and H.I. Yamamura Eur. J. Pharmacol. 321 1997 R1
30. G.M.P. Giblin, C.T. O'Shaughnessy, A. Naylor, W.L. Mitchell, A.J. Eatherton, B.P. Slingsby, D.A. Rawlings, P. Goldsmith, A.J. Brown, C.P. Haslam, N.M. Clayton, A.W. Wilson, I.P. Chessell, A.R. Wittington, and R. Green J. Med. Chem. 50 2007 2597
31. T. Ostenfeld, J. Price, M. Albanese, J. Bullman, F. Guillard, I. Meyer, R. Leeson, C. Costantin, L. Ziviani, P.F. Nocini, and S. Milleri Clin. J. Pain 27 2011 668
32. O. Ofek, M. Karsak, N. Leclerc, M. Fogel, B. Frenkel, K. Wright, J. Tam, M. Attar-Namdar, V. Kram, E. Shohami, R. Mechoulam, A. Zimmer, and I. Bab Proc. Natl. Acad. Sci. U.S.A. 103 2006 696
33. J. Palazuelos, N. Davoust, B. Julien, E. Hatterer, T. Aguado, R. Mechoulam, C. Benito, J. Romero, A. Silva, M. Guzman, S. Nataf, and I. Galve-Roperh J. Biol. Chem. 283 2008 13320
34. For recent reviews on CB2R as a target for inflammatory and immune-related diseases see: (a) N. Leleu-Chavain, M. Body-Malapel, J. Spencer, P. Chavatte, P. Desreumaux, and R. Millet Curr. Med. Chem. 12 2012 3457
35. N. Leleu-Chavain, P. Desreumaux, P. Chavatte, and R. Millet Curr. Mol. Pharmacol. 6 2013 183
36. M. Karsak, E. Gaffal, R. Date, L. Wang-Eckhardt, J. Rehnelt, S. Petrosino, K. Starowicz, R. Steuder, E. Schlicker, B. Cravatt, R. Mechoulam, R. Buettner, S. Werner, V. Di Marzo, T. Tuting, and A. Zimmer Science 316 2007 1494
37. E.S. Kimball, C.R. Schneider, N.H. Wallace, and P.J. Hornby Am. J. Physiol. Gastrointest. Liver Physiol. 291 2006 G364
38. A. Tourteau, V. Andrzejak, M. Body-Malapel, L. Lemaire, A. Lemoine, R. Mansouri, M. Djouina, N. Renault, J. El Bakali, P. Desreumaux, G.G. Muccioli, D.M. Lambert, P. Chavatte, B. Rigo, N. Leleu-Chavaina, and R. Millet Bioorg. Med. Chem. 21 2013 5383
39. S. Steffens, N.R. Veillard, C. Arnaud, G. Pelli, F. Burger, C. Staub, M. Karsak, A. Zimmer, J.L. Frossard, and F. Mach Nature 434 2005 782
40. R.B. Zurier, R.G. Rossetti, J.H. Lane, J.M. Goldberg, S.A. Hunter, and S.H. Burstein Arthritis Rheum. 41 1998 163
41. R.B. Zurier, R.G. Rossetti, S.H. Burstein, and B. Bidinger Biochem. Pharmacol. 65 2003 649
42. M.A. Tepper, R.B. Zurier, and S.H. Burstein Bioorg. Med. Chem. 22 2014 3245
43. F. Montecucco, F. Burger, F. Mach, and S. Steffens Am. J. Physiol. Heart Circ. Physiol. 294 2008 H1145
44. E. Raborn, F. Marciano-Cabral, N. Buckley, B. Martin, and G. Cabral J. Neuroimmune Pharmacol. 3 2008 117
45. P. Sacerdote, P. Massi, A.E. Panerai, and D. Parolaro J. Neuroimmunol. 109 2000 155
46. F. Montecucco, V. Di Marzo, R.F. da Silva, N. Vuilleumier, L. Capettini, S. Lenglet, S. Pagano, F. Piscitelli, S. Quintao, M. Bertolotto, P. Pelli, K. Galan, L. Pilet, K. Kuzmanovic, F. Burger, B. Pane, G. Spinella, V. Braunersreuther, A. Gayet-Ageron, A. Pende, G.L. Viviani, D. Palombo, F. Dallegri, P. Roux-Lombard, A.S. Robson, R.A.S. Santos, N. Stergiopulos, S. Steffens, and F. Mach Eur. Heart J. 33 2012 846
47. L. Di, and E.H. Kerns Curr. Opin. Chem. Biol. 7 2003 402
48. (a) Openeye Scientific. OMEGA; OpenEye Scientific Software: Santa Fe, NM, http://www.eyesopen.com/omega
49. P.C. Hawkins, A.G. Skillman, G.L. Warren, B.A. Ellingson, and M.T. Stahl J. Chem. Inf. Model. 50 2010 572 584
50. P.C. Hawkins, and A. Nicholls J. Chem. Inf. Model. 52 2012 2919 2936
51. I.M. Westwood, A. Kawamura, A.J. Russell, J. Sandy, S.G. Davies, and E. Sim Comb. Chem. High Throughput Screening 14 2011 117
52. N. Laurieri, M.H.J. Crawford, A. Kawamura, I.M. Westwood, J. Robinson, A.M. Fletcher, S.G. Davies, E. Sim, and A.J. Russell J. Am. Chem. Soc. 132 2010 3238
53. M.M.P. Lufino, A.M. Silva, A.H. Németh, J. Alegre-Abarrategui, A.J. Russell, and R. Wade-Martins Hum. Mol. Genet. 22 2013 5173
54. Openeye Scientific. ROCS; OpenEye Scientific Software: Santa Fe, NM, http://www.eyesopen.com/rocs
55. T. Cheeseright, M. Mackey, S. Rose, and A. Vinter Expert Opin. Drug Discov. 2 2007 131 144 Forge v10; http://www.cresset-group.com/products/forge/
56. Grant, J. A.; Pickup, B. T. Comp Simulation of Biomolecular Systems. Springer Science and Business Media: Dordrecht, 1997; Vol 3.
57. J.A. Grant, M.A. Gallardo, and B.T. Pickup J. Comput. Chem. 17 1996 1654
58. http://www.discoverx.com/target-data-sheets/gpcr/cnr2.
59. V.J. Ram Arch. Pharm. 313 1980 108
60. E.S.H. El Ashry, E.S. Ramadan, H.M.A. Hamid, and M. Hagar Synlett 2004 723
61. A.B. Tomchin, O.Y. Uryupov, T.I. Zhukova, T.A. Kuznetsova, M.V. Kostycheva, and A.V. Smirnov Pharm. Chem. J. 31 1997 125
62. C.A. Hunter Angew. Chem. Int. Ed. 43 2004 5310
63. M. Rinaldi-Carmona, B. Calandra, D. Shire, M. Bouaboula, D. Oustric, F. Barth, P. Casellas, P. Ferrara, and G. Le Fur J. Pharmacol. Exp. Ther. 278 1996 871
64. Adams, C. M.; Chamoin, S.; Hu, Q.-Y.; Zhang, C. WO 2010/130794.
65. G.A. Molander, and B. Canturk Angew. Chem. Int. Ed. 121 2009 9404
66. H.J. Schneider, and V. Hoppen J. Org. Chem. 43 1978 3866
67. A.P. Hill, and R.J. Young Drug Discovery Today 15 2010 648
68. P. Leeson, and B. Springthorpe Nat. Rev. Drug Disc. 6 2007 881
69. M. Shultz Bioorg. Med. Chem. Lett. 23 2013 5980
70. A. Tarcsay, and G.M. Keseru J. Med. Chem. 56 2013 1789
71. M.J. Waring Expert Opin. Drug Discov. 5 2010 235
72. J.A. Arnott, and S.L. Planey Expert Opin. Drug Discov. 7 2012 863
73. C. Abad-Zapatero, and D. Blasi Mol. Inform. 30 2011 122
74. M. Shultz Bioorg. Med. Chem. Lett. 23 2013 5992
75. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Delivery Rev. 23 1997 3
76. S.J. Teague, A.M. Davis, P.D. Leeson, and T. Oprea Angew. Chem. Int. Ed. 38 1999 3743
77. Cyprotex; Vol. http://www.cyprotex.com/admepk/physicochemical-properties/turbidimetric-solubility/.
78. E.H. Kerns, L. Di, and G.T. Carter Curr. Drug Metab. 9 2008 879
79. Cyprotex; Vol. http://www.cyprotex.com/admepk/in-vitro-metabolism/microsomal-stability/.
80. J. McLure, J. Miners, and D. Birkett Br. J. Clin. Pharmacol. 49 2000 453
81. V. Purohit, and A.K. Basu Chem. Res. Toxicol. 13 2000 673
82. Cyprotex Table 1, Classification of brain uptake using Cyprotex's MDR1-MDCK Permeability. http://www.cyprotex.com/admepk/in-vitro-permeability/mdr1-mdck-permeability/.
83. http://www.cerep.fr/Cerep/Users/pages/productsservices/GPCRPlatform.asp.
84. M.A. Fabian, W.H. Biggs III, D.K. Treiber, C.E. Atteridge, M.D. Azimioara, M.G. Benedetti, T.A. Carter, P. Ciceri, P.T. Edeen, M. Floyd, J.M. Ford, M. Galvin, J.L. Gerlach, R.M. Grotzfeld, S. Herrgard, D.E. Insko, M.A. Insko, A.G. Lai, J.-M. Lélias, S.A. Mehta, Z.V. Milanov, A.M. Velasco, L.M. Wodicka, H.K. Patel, P.P. Zarrinkar, and D.J. Lockhart Nat. Biotechnol. 23 2005 329
85. M.W. Karaman, S. Herrgard, D.K. Treiber, P. Gallant, C.E. Atteridge, B.T. Campbell, K.W. Chan, P. Ciceri, M.I. Davis, P.T. Edeen, R. Faraoni, M. Floyd, J.P. Hunt, D.J. Lockhart, Z.V. Milanov, M.J. Morrison, G. Pallares, K.K. Patel, S. Pritchard, L.M. Wodicka, and P.P. Zarrinkar Nat. Biotechnol. 26 2008 127
86. (c) http://www.discoverx.com/services/drug-discovery-development-services/kinase-profiling/kinomescan.
87. A.B. Pangborn, M.A. Giardello, R.H. Grubbs, R.K. Rosen, and F.J. Timmers Organometallics 15 1996 1518
88. J.M.Z. Gladych, R. Hornby, J.H. Hunt, and D. Jack J. Med. Chem. 15 1972 277 281
89. B.M. Trost, S. Malhotra, and W.H. Chan J. Am. Chem. Soc. 133 2011 7328
90. K.L. Vine, J.M. Locke, M. Ranson, S.G. Pyne, and J.B. Bremner J. Med. Chem. 50 2007 5109