Knowledge-based analysis of multi-potent G-protein coupled receptors ligands

European Journal of Medicinal Chemistry

Volumn 45, Issue 12, 2010, Pages 5708-5717

  Faure, Patricia ^a   Dubus, Elodie ^a   Ijjaali, Ismail ^a   Morlire, Christelle ^a   Barberan, Olivier ^a   Petitet, Franois ^a  

^a Aureus Pharma   (France)

Author keywords

G protein coupled receptors; Multi potent ligands; Pharmacological selectivity; Structure activity relationships

Indexed keywords

G PROTEIN COUPLED RECEPTOR;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CHEMICAL STRUCTURE; DATA BASE; DRUG TARGETING; PROTEIN INTERACTION; PROTEIN TARGETING; QUANTITATIVE ANALYSIS; STRUCTURE ACTIVITY RELATION;

LIGANDS; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; RECEPTORS, G-PROTEIN-COUPLED; STEREOISOMERISM;

EID: 78649329699     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.09.027     Document Type: Article

References (58)

1. A.L. Hopkins Network pharmacology Nat. Chem. Biol. 4 2008 682 690
2. G.V. Paolini, R.H.B. Shapland, W.P. van Hoorn, J.S. Mason, and A.L. Hopkins Global mapping of pharmacological space Nat. Biotechnol. 24 2006 805 815
3. M.J. Keiser, B.L. Roth, B.N. Armbruster, P. Ernsberger, J.J. Irwin, and B.K. Shoichet Relating protein pharmacology by ligand chemistry Nat. Biotechnol. 25 2007 197 206
4. M.J. Keiser, V. Setola, J.J. Irwin, C. Laggner, A.I. Abbas, S.J. Hufeisen, N.H. Jensen, M.B. Kuijer, R.C. Matos, T.B. Tran, R. Whaley, R.A. Glennon, J. Hert, K.L. Thomas, D.D. Edwards, B.K. Shoichet, and B.L. Roth Predicting new molecular targets for known drugs Nature 462 2009 175 182
5. M.A. Yldrm, K.I. Goh, M.E. Cusik, A.L. Barabási, and M. Vidal Drug-target network Nat. Biotechnol. 25 2007 1119 1126
6. T.K. Attwood, and J.B. Findlay Fingerprinting G-protein-coupled receptors Protein Eng. 7 1994 195 203
7. L.F. Kolakowski Jr. GCRDb: a G-protein-coupled receptor database Receptors Channels 2 1994 1 7
8. C.M. Rominger, W.L. Bee, R.A. Copeland, E.A. Davenport, A. Gilmartin, R. Gontarek, K.R. Hornberger, L.A. Kallal, Z. Lai, K. Lawrie, Q. Lu, L. McMillan, M. Truong, P.J. Tummino, B. Turunen, M. Will, W.J. Zuercher, and D.H. Rominger Evidence for allosteric interactions of antagonist binding to the smoothened receptor J. Pharmacol. Exp. Ther. 329 2009 995 1005
9. J.R. Didsbury, T. Dyakonov, S.N. Haydar, M.L. Jones, F.F. Li, C.J. Markworth, J.J. Scicinski, L.A. Cabana, J. Mathew, D.N. Middlemiss, G.C. Collupy, F.J. Schoenen, J.F. Burns, D.N. Vanvliet. Patent WO07134169, 2007.
10. A. Nakazato, T. Okubo, D. Nozawa, T. Tamita, L. Kennis. Patent WO06001511, 2006.
11. V. Butterweck, A. Nahrstedt, J. Evans, S. Hufeisen, L. Rauser, J. Savage, B. Popadak, P. Ernsberger, and B.L. Roth In vitro receptor screening of pure constituents of St. John's wort reveals novel interactions with a number of GPCRs Psychopharmacology 162 2002 193 202
12. U. Simmen, I. Bobirnac, C. Ullmer, H. Lübbert, K. Berger Büter, W. Schaffner, and P. Schoeffter Antagonist effect of pseudohypericin at CRF1 receptors Eur. J. Pharmacol. 458 2003 251 256
13. T.D. Aicher, D.R. Benesh, M.J. Blanco-Pillado, G.S. Cortez, T.M. Groendyke, A. Khilevich, J.A. Knobelsdorf, F.P. Marmsater, J.M. Schkeryantz, T.P. Tang. Patent WO06057860, 2006.
14. H. Geneste, D. Sauer, W. Braje, W. Amberg, M. Mezler, M.H.M. Bakker. Patent US20080300260, 2008.
15. 2A-D2 receptor heteromers J. Med. Chem. 52 2009 5590 5602
16. T. Klabunde, and A. Evers GPCR antitarget modelling: pharmacophore models for biogenic amine binding GPCRs to avoid GPCR-mediated side effects ChemBioChem 6 2005 876 889
17. M.R. Marzabadi, J. Wetzel, J.E. DeLeon, Y. Jiang, C.-A. Chen, K. Lu. Patent US6727264, 2004.
18. T.J. Howe, G. Bhalay, D.M. Le Grand, T. Storz. Patent US6670379, 2003.
19. I. Islam, D.S. Dhanoa, J.M. Finn, P. Du, C. Gluchowski, Y.T. Jeon. Patent US6211241, 2001.
20. K.M. Meyers, J. Méndez-Andino, A.O. Colson, X.E. Hu, J.A. Wos, M.C. Mitchell, K. Hodge, J. Howard, J.L. Paris, M.E. Dowty, C.M. Obringer, and O. Reizes Novel pyrazolopiperazinone- and pyrrolopiperazinone-based MCH-R1 antagonists Bioorg. Med. Chem. Lett. 17 2007 657 664
21. J.R. Tagat, S.W. McCombie, R.W. Steensma, S. Lin, D.V. Nazareno, B. Baroudy, N. Ventuno, S. Xu, and J. Liu Piperazine-based CCR5 antagonists as HIV-1 inhibitors. I: 2(S)-methyl piperazine as a key pharmacophore element Bioorg. Med. Chem. Lett. 11 2001 2143 2146
22. S.W. McCombie, J.R. Tagat, S.F. Vice, S.I. Lin, R. Steensma, A. Palani, B.R. Neustadt, B.M. Baroudy, J.M. Strizki, M. Endres, K. Cox, N. Dan, and C.C. Chou Piperazine-based CCR5 antagonists as HIV-1 inhibitors. III: synthesis, antiviral and pharmacokinetic profiles of symmetrical heteroaryl carboxamides Bioorg. Med. Chem. Lett. 13 2003 567 571
23. T. Blackburn. Patent WO04014307, 2004.
24. M.J. Konkel, M. Packiarajan, H. Chen, U.P. Topiwala, H. Jimenez, I.J. Talisman, H. Coate, and M.W. Walker Amino substituted analogs of 1-phenyl-3-phenylimino-2-indolones with potent galanin Gal3 receptor binding affinity and improved solubility Bioorg. Med. Chem. Lett. 16 2006 3950 3954
25. G.V. De Lucca, U.T. Kim, C. Johnson, B.J. Vargo, P.K. Welch, M. Covington, P. Davies, K.A. Solomon, R.C. Newton, G.L. Trainor, C.P. Decicco, and S.S. Ko Discovery and structure-activity relationship of N-(ureidoalkyl)- benzyl-piperidines as potent small molecule CC chemokine receptor-3 (CCR3) antagonists J. Med. Chem. 45 2002 3794 3804
26. G.V. De Lucca, U.T. Kim, B.J. Vargo, J.V. Duncia, J.B. Santella 3rd, D.S. Gardner, C. Zheng, A. Liauw, Z. Wang, G. Emmett, D.A. Wacker, P.K. Welch, M. Covington, N.C. Stowell, E.A. Wadman, A.M. Das, P. Davies, S. Yeleswaram, D.M. Graden, K.A. Solomon, R.C. Newton, G.L. Trainor, C.P. Decicco, and S.S. Ko Discovery of CC chemokine receptor-3 (CCR3) antagonists with picomolar potency J. Med. Chem. 48 2005 2194 2211
27. T. Austin, D. O'Sullivan, M. Perry, B. Springthorpe. Patent WO07011293, 2007.
28. T. Troxler, A. Enz, D. Hoyer, D. Langenegger, P. Neumann, P. Pfäffli, P. Schoeffter, and K. Hurth Ergoline derivatives as highly potent and selective antagonists at the somatostatin sst1 receptor Bioorg. Med. Chem. Lett. 18 2008 979 982
29. J.J. Li, K.G. Carson, B.K. Trivedi, W.S. Yue, Q. Ye, R.A. Glynn, S.R. Miller, D.T. Connor, B.D. Roth, J.R. Luly, J.E. Low, D.J. Heilig, W. Yang, S. Qin, and S. Hunt Synthesis and structure-activity relationship of 2-amino-3-heteroaryl-quinoxalines as non-peptide, small-molecule antagonists for interleukin-8 receptor Bioorg. Med. Chem. 11 2003 3777 3790
30. J.M. Keith, L.A. Gomez, A.J. Barbier, S.J. Wilson, J.D. Boggs, C. Mazur, L. Aluisio, T.W. Lovenberg, and N.I. Carruthers Pyrrolidino- tetrahydroisoquinolines bearing pendant heterocycles as potent dual H3 antagonist and serotonin transporter inhibitors Bioorg. Med. Chem. Lett. 17 2007 4374 4377
31. B. Wroblowski, M.J. Wigglesworth, P.G. Szekeres, G.D. Smith, S.S. Rahman, N.H. Nicholson, A.I. Muir, A. Hall, J.P. Heer, S.L. Garland, and W.J. Coates The discovery of a selective, small molecule agonist for the MAS-related gene x1 receptor J. Med. Chem. 52 2009 818 825
32. J. Jin, M. An, A. Sapienza, N. Aiyar, D. Naselsky, H.M. Sarau, J.J. Foley, K.L. Salyers, S.D. Knight, R.M. Keenan, R.A. Rivero, D. Dhanak, and S.A. Douglas Urotensin-II receptor antagonists: synthesis and SAR of N-cyclic azaalkyl benzamides Bioorg. Med. Chem. Lett. 18 2008 3950 3954
33. P. Kitabgi, W. Rostene, M. Dussaillant, A. Schotte, P.M. Laduron, and J.P. Vincent Two populations of neurotensin binding sites in murine brain: discrimination by the antihistamine levocabastine reveals markedly different radioautographic distribution Eur. J. Pharmacol. 140 1987 285 293
34. 1-adrenoceptors in human and pig brain membranes Naunyn Schiemedebergs Arch. Pharmacol. 335 1987 226 230
35. D.A. Nelson, and E.W. Taylor Spiroxatrine: a selective serotonin1A receptor antagonist Eur. J. Pharmacol. 124 1986 207 208
36. A.D. Michel, D.N. Loury, and R.L. Whiting Identification of a single alpha 1-adrenoceptor corresponding to the alpha 1A-subtype in rat submaxillary gland Br. J. Pharmacol. 98 1989 883 889
37. P.H. Andersen The dopamine inhibitor GBR 12909: selectivity and molecular mechanism of action Eur. J. Pharmacol. 166 1989 493 504
38. J.A. Clark, L. Liu, M. Price, B. Hersh, M. Edelson, and G.W. Pasternak Kappa opiate receptor multiplicity: evidence for two U50,488-sensitive kappa 1 subtypes and a novel kappa 3 subtype J. Pharmacol. Exp. Ther. 251 1989 461 468
39. R.L. Weinshank, J.M. Zgombick, M. Macchi, N. Adham, H. Lichtblau, T.A. Branchek, and P.R. Hartig Cloning, expression, and pharmacological characterization of a human alpha 2B-adrenergic receptor Mol. Pharmacol. 38 1990 681 688
40. M.D. De Backer, W. Gommeren, H. Moereels, G. Nobels, P. Van Gompel, J.E. Leysen, and W.H. Luyten Genomic cloning, heterologous expression and pharmacological characterization of a human histamine H1 receptor Biochem. Biophys. Res. Commun. 197 1993 1601 1608
41. K. Hashimoto, and E.D. London Further characterization of [3H]ifenprodil binding to sigma receptors in rat brain Eur. J. Pharmacol. 236 1993 159 163
42. 3 receptors and sigma sites in the bovine caudate nucleus Eur. J. Pharmacol. 242 1993 R1 R2
43. P.M. Beart, M.C. Ryan, L.D. Mercer, J. Bevyn, and M.G. Wong Heterocyclic amino alcohols related to ifenprodil as.sigma. receptor ligands: binding and conformational analyses Eur. J. Pharmacol. Mol. Pharmacol. 269 1994 193 200
44. B.L. Roth, S.C. Craigo, M.S. Choudhary, A. Uluer, F.J. Monsma Jr., Y. Shen, H.Y. Meltzer, and D.R. Sibley Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors J. Pharmacol. Exp. Ther. 268 1994 1403 1410
45. D.T. Beattie, I.J. Beresford, H.E. Connor, F.H. Marshall, A.B. Hawcock, R.M. Hagan, J. Bowers, P.J. Birch, and P. Ward The pharmacology of GR203040, a novel, potent and selective non-peptide tachykinin NK1 receptor antagonist Br. J. Pharmacol. 116 1995 3149 3157
46. A. Alves-Rodrigues, R. Leurs, E. Willems, and H. Timmerman Binding of clozapine metabolites and analogs to the histamine H3 receptor in rat brain cortex Arch. Pharm. 329 1996 413 416
47. 2A subtype Br. J. Pharmacol. 121 1997 1721 1729
48. N. Zaveri, W.E. Polgar, C.M. Olsen, A.B. Kelson, P. Grundt, J.W. Lewis, and L. Toll Characterization of opiates, neuroleptics, and synthetic analogs at ORL1 and opioid receptors Eur. J. Pharmacol. 428 2001 29 36
49. J. Witherington, V. Bordas, D.G. Cooper, I.T. Forbes, A.D. Gribble, R.J. Ife, T. Berkhout, J. Gohil, and P.H. Groot Conformationally restricted indolopiperidine derivatives as potent CCR2B receptor antagonists Bioorg Med. Chem. Lett. 11 2001 2177 2180
50. W.L. Rumsey, D. Aharony, R.A. Bialecki, B.M. Abbott, H.G. Barthlow, R. Caccese, S. Ghanekar, D. Lengel, M. McCarthy, B. Wenrich, B. Undem, C. Ohnmacht, A. Shenvi, J.S. Albert, F. Brown, P.R. Bernstein, and K. Russell Pharmacological characterization of ZD6021: a novel, orally active antagonist of the tachykinin receptors J. Pharmacol. Exp. Ther 298 2001 307 315
51. H. Takayama, H. Ishikawa, M. Kurihara, M. Kitajima, N. Aimi, D. Ponglux, F. Koyama, K. Matsumoto, T. Moriyama, L.T. Yamamoto, K. Watanabe, T. Murayama, and S. Horie Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands J. Med. Chem. 45 2002 1949 1956
52. C. Sur, P.J. Mallorga, M. Wittmann, M.A. Jacobson, D. Pascarella, J.B. Williams, P.E. Brandish, D.J. Pettibone, E.M. Scolnick, and P.J. Conn N-desmethylclozapine, an allosteric agonist at muscarinic 1 receptor, potentiates N-methyl-d-aspartate receptor activity Proc. Natl. Acad. Sci. 100 2003 13674 13679
53. 1 receptor antagonist Neurosci. Lett. 361 2004 132 135
54. G.I. Bell, T. Reisine, K. Yasuda. Patent US6096513, 2000.
55. R. DeHaven, E. Gauntner, P. Little, W.Y. Zhang. Patent US20020156052, 2002.
56. International Union for Basic and Clinical Pharmacology, IUPHAR www.iuphar.org
57. G-Protein Coupled Receptor Database, GPCRDB www.gpcr.org
58. Aureus-Pharma S.A. www.aureus-pharma.com