Structure-kinetics relationships of Capadenoson derivatives as adenosine A1 receptor agonists

European Journal of Medicinal Chemistry

Volumn 101, Issue , 2015, Pages 681-691

  Louvel, Julien ^a   Guo, Dong ^a   Soethoudt, Marjolein ^a   Mocking, Tamara A M ^a   Lenselink, Eelke B ^a   Mulder Krieger, Thea ^a   Heitman, Laura H ^a   Ijzerman, Adriaan P ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Adenosine A1 receptor; Extracellular loops; Residence time; Structure affinity relationships; Structure kinetics relationships

Indexed keywords

2 AMINO 4 (4 METHOXYPHENYL) 6 (THIAZOL 4 YLMETHYLTHIO)PYRIDINE 3,5 DICARBONITRILE; 2 AMINO 6 [[2 (4 CHLOROPHENYL)THIAZOL 4 YL]METHYLTHIO] 4 (4 METHOXYPHENYL)PYRIDINE 3,5 DICARBONITRILE; ADENOSINE A1 RECEPTOR AGONIST; CAPADENOSON; THIAZOLE; UNCLASSIFIED DRUG; ADENOSINE A1 RECEPTOR; AMINOPYRIDINE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; BINDING KINETICS; BIOLOGICAL ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; LIPOPHILICITY; MEAN RESIDENCE TIME; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; KINETICS; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ADENOSINE A1 RECEPTOR AGONISTS; AMINOPYRIDINES; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RECEPTOR, ADENOSINE A1; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 84937840389     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.07.023     Document Type: Article

References (49)

1. a) B.B. Fredholm, A.P. IJzerman, K.A. Jacobson, J. Linden, C.E. Müller, International Union of basic and clinical pharmacology. LXXXI. Nomenclature and classification of adenosine receptorsd - an update, Pharmacol. Rev. 63 (2011) 1-34;
2. b) K.A. Jacobson, Z.G. Gao, Adenosine receptors as therapeutic targets, Nat. Rev. Drug Disc. 5 (2006) 247-264;
3. c) B.B. Fredholm, J.F. Chen, S.A. Masino, J.M. Vaugeois, Actions of adenosine at its receptors in the CNS: insights from knockouts and drugs, Annu. Rev. Pharmacol. Toxicol. 45 (2005) 385-412.
4. Bayer Aktiengesellschaft WO2001025210.
5. a) M.W. Beukers, L.C.W. Chang, J.K. von Frijtag Drabbe Künzel, T. Mulder-Krieger, R.F. Spanjersberg, J. Brussee, A.P. IJzerman, New, non-adenosine, highpotency agonists for the human adenosine A2B receptor with an improved selectivity profile compared to the reference agonist N-ethylcarboxamidoadenosine, J. Med. Chem.47 (2004) 3707-3709;
6. 1 receptor, J. Med. Chem. 48 (2005) 2045-2053.
7. a) Otsuka Pharmaceuticals WO2005105778 A2;
8. Otsuka Pharmaceuticals US20120022077 A1.
9. 1 receptor with tunable residence time. A case for non-ribose 4-amino-6-aryl-5-cyano-2-thiopyrimidines, J. Med. Chem. 57 (2014) 3213-3222.
10. R.A. Prentis, Y. Lis, S.R. Walker, Pharmaceutical innovation by the seven UK-owned pharmaceutical companies (1964-1985), Br. J. Clin. Pharmacol. 25 (1988) 387-396.
11. a) D.A. Smith, B.C. Jones, D.K. Walker, Design of drugs involving the concepts and theories of drug metabolism and pharmacokinetics, Med. Res. Rev. 16 (1996) 243-266;
12. b) R. Zhang, F. Monsma, The importance of drug-target residence time, Curr. Opin. Drug. Disc. Dev. 12 (2009) 488-496;
13. c) R. Zhang, F. Monsma, Binding kinetics and mechanism of action: toward the discovery and development of better and best in class drugs, Exp. Opin. Drug Disc. 5 (2010) 1023-1029;
14. d) R.A. Copeland, D.L. Pompliano, T.D. Meek, Drug-target residence time and its implications for lead optimization, Nat. Rev. Drug Discov. 5 (2006) 730-739.
15. 3 receptor, Br. J. Pharmacol.(2006) 927-937;
16. b) I. Van Liefde, G. Vauquelin, SartaneAT1 receptor interactions: In vitro evidence for insurmountable antagonism and inverse agonism, Mol. Cell. Endocrinol. 302 (2008) 237-243.
17. R.A. Copeland, The dynamics of drug-target interactions: drug-target residence time and its impact on efficacy and safety, Exp. Opin. Drug Disc. 5 (2010) 305-310.
18. Bayer Healthcare Aktiengesellschaft clinical trial report BAY 68-4986/12679.
19. Bayer Healthcare Aktiengesellschaft WO2007073855 A1.
20. O. Oniga, I. Grosu, S. Mager, I. Simiti, Heterocycles LXXVIII. Electrophilic substitution of 20′-phenyl-4R-2,4′-bisthiazoles, Monatsh. Chem. 129 (1998) 661-669.
21. 1 adenosine receptors, Naunyn-Schmiedeberg's Arch. Pharmacol. 336 (1987) 204-210.
22. D. Guo, E.J. van Dorp, T. Mulder-Krieger, J.P. van Veldhoven, J. Brussee, A.P. IJzerman, L.H. Heitman, Dual-point competition association assay: a fast and high-throughput kinetic screening method for assessing ligand-receptor binding kinetics, J. Biomol. Screen. 18 (2013) 309-320.
23. R. Wilcken, M.O. Zimmermann, A. Lange, A.C. Joerger, F.M. Boeckler, Principles and applications of halogen bonding in medicinal chemistry and chemical biology, J. Med. Chem. 56 (2013) 1363-1388.
24. J.J. Dynes, F.L. Baudais, R.K. Boyd, Inter-ring dihedral angles in polychlorinated biphenyls from photoelectron spectroscopy, Can. J. Chem. 63 (1985) 1292-1299.
25. Ligand efficiencies were calculated using the equation LE (kcal/mol heavy atom)= (1.374/N) pKi (at 293 K) clogP values were calculated using Chemaxon Marvin: http://www.chemaxon.com/marvin/sketch/index.jsp.
26. A.L. Hopkins, C.R. Groom, A. Alex, Ligand efficiency: a useful metric for lead selection, Drug Discov. Today 9 (2004) 430-431.
27. a) C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Freeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug. Deliv. Rev. 23 (1997) 3-25;
28. ibid Adv. Drug. Deliv. Rev. 46 (2001) 3-26.
29. 2A receptors in rat brain, Eur. J. Pharmacol. 411 (2001) 205-210.
30. 2B receptor antagonists and a new radioligand with subnanomolar affinity and subtype specificity, J. Med. Chem. 52 (2009) 3994-4006
31. 3 adenosine receptors, Bioorg. Med. Chem. Lett. 12 (2002) 501-503.
32. 1 selective adenosine agonists, J. Med. Chem. 28 (1985) 1383-1384.
33. 2A receptor, Mol. Pharmacol. 81 (2012) 475-487.
34. P. Schmidtke, F. Javier Luque, J.B. Murray, X. Barril, Shielded hydrogen bonds as structural determinants of binding kinetics: application in drug design, J. Am. Chem. Soc. 133 (2011) 18903-18910.
35. P. Auffinger, F.A. Hays, E. Westhoff, P. Shing Ho, Halogen bonds in biological molecules, Proc. Nat. Acad. Sci. U. S. A. 101 (2004) 16789-16794.
36. D. Guo, J.M. Hillger, A.P. IJzerman, L.H. Heitman, Drug-target residence time e a case for G protein-coupled receptors, Med. Res. Rev. 34 (2014) 856-892.
37. 2B receptor antagonists and a new radioligand with subnanomolar affinity and subtype specificity, J. Med. Chem. 52 3994-4006.
38. M.P. Jacobson, D.L. Pincus, C.S. Rapp, T.J. Day, B. Honig, D.E. Shaw, R.A. Friesner, A hierarchical approach to all-atom protein loop prediction, Proteins 55 (2004) 351-367.
39. M.P. Jacobson, R.A. Friesner, Z. Xiang, B. Honig, On the role of the crystal environment in determining protein side-chain conformations, J. Mol. Biol. 320 (2002) 597-608.
40. Schrödinger, Release 2014-3: Prime, Version 3.7, Schrödinger, LLC, New York, NY, 2014.
41. 2A adenosine receptor, Sci. (N.Y.) 332 (2011) 322-327.
42. V. Isberg, B. Vroling, R. van der Kant, K. Li, G. Vriend, D. Gloriam, GPCRDB: an information system for G protein-coupled receptors, Nucleic Acids Res. 42 (2014) D422-D425.
43. a) V. Katrich, M. Rueda, R. Abagyan, Ligand-guided receptor optimization, Methods Mol. Biol. 857 (2012) 189-205;
44. 2A receptor antagonists, J. Med. Chem. 53 (2010) 1799-1809;
45. c) V. Katritch, I. Kufareva, R. Abagyan, Structure based prediction of subtypeselectivity for adenosine receptor antagonists, Neuropharmacology 60 (2011) 108-115;
46. 1 adenosine receptor antagonists, PLoS ONE 7 (2012) 1-9;
47. e) I. Kufareva, V. Katritch, Participants of Gpcr dock 2013, S. Grudinin, R.C. Stevens, R. Abagyan, Advances in GPCR modeling evaluated by the GPCR dock 2013 assessment: meeting new challenges, Structure 22 (2014) 1120-1139.
48. M.M. Mysinger, M. Carchia, J.J. Irwin, B.K. Shoichet, Directory of useful decoys, enhanced (DUD-E): better ligands and decoys for better benchmarking, J. Med. Chem. 55 (2012) 6582-6594.
49. Small-Molecule Drug Discovery Suite 2014-3, Glide, Version 6.4, Schrödinger, LLC, New York, NY, 2014.