Recognition of Privileged Structures by G-Protein Coupled Receptors

Journal of Medicinal Chemistry

Volumn 47, Issue 4, 2004, Pages 888-899

  Bondensgaard, Kent ^a   Ankersen, Michael ^a   Thøgersen, Henning ^a   Hansen, Birgit S ^a   Wulff, Birgitte S ^a   Bywater, Robert P ^a  

^a NOVO NORDISK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLINDOLE DERIVATIVE; 3 AMINO 3 METHYL N [2,3,4,5 TETRAHYDRO 2 OXO 1 [[2' (1H TETRAZOL 5 YL) 1,1' BIPHENYL 4 YL]METHYL] 1H 1 BENZAZEPIN 3 YL]BUTANAMIDE; ANGIOTENSIN 2 RECEPTOR; BIPHENYL DERIVATIVE; G PROTEIN COUPLED RECEPTOR; GROWTH HORMONE SECRETAGOGUE RECEPTOR; IBUTAMOREN; INDAN DERIVATIVE; LIGAND; LOSARTAN; MELANOCORTIN 4 RECEPTOR; PIPERIDINE; SEROTONIN 6 RECEPTOR; SPIRO COMPOUND; TETRAZOLE DERIVATIVE;

ARTICLE; BINDING AFFINITY; HYDROPHOBICITY; LIGAND BINDING; MUTAGENESIS; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; BINDING SITES; BIPHENYL COMPOUNDS; CELL LINE; CONSERVED SEQUENCE; CRICETINAE; INDANS; INDOLES; LIGANDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PIPERIDINES; RECEPTOR, ANGIOTENSIN, TYPE 1; RECEPTOR, MELANOCORTIN, TYPE 4; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, SEROTONIN; SEQUENCE ALIGNMENT; SPIRO COMPOUNDS; TETRAZOLES;

EID: 0842304428     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0309452     Document Type: Article

References (50)

1. Evans, B. E.; Rittle, K. E.; Bock, M. G.; Dipardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. Methods for Drug Discovery - Development of Potent, Selective, Orally Effective Cholecystokinin Antagonists. J. Med. Chem. 1988, 31, 2235-2246.
2. Patchett, A. A.; Nargund, R. P.; Tata, J. R.; Chen, M. H.; Barakat, K. J.; Johnston, D. B. R.; Cheng, K.; Chan, W. W. S.; Butler, B.; Hickey, G.; Jacks, T.; Schleim, K.; Pong, S. S.; Chaung, L. Y. P.; Chen, H. Y.; Frazier, E. ; Leung, K. H.; Chiu, S. H. L.; Smith, R. G. Design and Biological-Activities of L-163,-191 (Mk-0677) - A Potent, Orally-Active Growth-Hormone Secretagogue. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7001-7005.
3. Palczewski, K.; Kumasaka, T.; Hori, T.; Behnke, C. A.; Motoshima, H.; Fox, B. A.; Le Trong, I.; Teller, D. C.; Okada, T.; Stenkamp, R. E.; Yamamoto, M.; Miyano, M. Crystal Structure of Rhodopsin: A G Protein-Coupled Receptor. Science 2000, 289, 739-745.
4. Labrou, N. E.; Bhogal, N.; Hurrell, C. R.; Findlay, J. B. C. Interaction of Met(297) in the Seventh Transmembrane Segment of the Tachykinin NK2 Receptor With Neurokinin A. J. Biol. Chem. 2001, 276, 37944-37949.
5. Renzetti, A. R.; Catalioto, R. M.; Criscuoli, M.; Cucchi, P.; Ferrer, C. ; Giolitti, A.; Guelfi, M.; Rotondaro, L.; Warner, F. J.; Maggi, C. A. Relevance of Aromatic Residues in Transmembrane Segments V to VII for Binding of Peptide and Nonpeptide Antagonists to the Human Tachykinin NK2 Receptor. J. Pharmacol. Exp. Ther. 1999, 290, 487-495.
6. Spalding, T. A.; Burstein, E. S.; Henderson, S. C.; Ducote, K. R.; Brann, M. R. Identification of a Ligand-Dependent Switch Within a Muscarinic Receptor. J. Biol. Chem. 1998, 273, 21563-21568.
7. Fong, T. M.; Huang, R. R. C.; Strader, C. D. Localization of Agonist and Antagonist Binding Domains of the Human Neurokinin-1 Receptor. J. Biol. Chem. 1992, 267, 25664-25667.
8. Strader, C. D.; Candelore, M. R.; Hill, W. S.; Sigal, I. S.; Dixon, R. A. F. Identification of 2 Serine Residues Involved in Agonist Activation of the Beta-Adrenergic-Receptor. J. Biol. Chem. 1989, 264, 13572-13578.
9. Strader, C. D.; Sigal, I. S.; Register, R. B.; Candelore, M. R.; Rands, E.; Dixon, R. A. F. Identification of Residues Required for Ligand-Binding to the Beta-Adrenergic-Receptor. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 4384-4388.
10. Pei, J. M.; Grishin, N. V. AL2CO: Calculation of Positional Conservation in a Protein Sequence Alignment. Bioinformatics 2001, 17, 700-712.
11. Willoughby, C. A.; Hutchins, S. M.; Rosauer, K. G.; Dhar, M. J.; Chapman, K. T.; Chicchi, G. G.; Sadowski, S.; Weinberg, D. H.; Patel, S.; Malkowitz, L. ; Di Salvo, J.; Pacholok, S. G.; Cheng, K. Combinatorial Synthesis of 3-(Amidoalkyl) and 3-(Aminoalkyl)-2- Arylindole Derivatives: Discovery of Potent Ligands for a Variety of G-Protein Coupled Receptors. Bioorg. Med. Chem. Lett. 2002, 12, 93-96.
12. Nargund, R.; Ye, Z.; Palucki, B. L., Bakshi, R. K., Patchett, A. A., Van der Ploeg, L. H. T. 1999, Patent No. WO 9964002.
13. Chiu, A. T.; McCall, D. E.; Price, W. A.; Wong, P. C.; Carini, D. J.; Duncia, J. V.; Wexler, R. R.; Yoo, S. E.; Johnson, A. L.; Timmermans, P. B. M. W. Nonpeptide Angiotensin-Ii Receptor Antagonists 0.7. Cellular and Biochemical Pharmacology of Dup-753, An Orally Active Antihypertensive Agent. J. Pharmacol. Exp. Ther. 1990, 252, 711-718.
14. Schoen, W. R.; Pisano, J. M.; Prendergast, T. K.; Wyvratt, M. J.; Fisher, M. H.; Cheng, K.; Chan, W. W. S.; Butler, B.; Smith, R. G.; Ball, R. G. A Novel 3-Substituted Benzazepinone Growth-Hormone Secretagogue (L-692,429). J. Med. Chem. 1994, 37, 897-906.
15. Hansen, B. S.; Raun, K.; Nielsen, K. K.; Johansen, P. B.; Mansen, T. K.; Peschke, B.; Lau, J.; Andersen, P. H.; Ankersen, M. Pharmacological Characterisation of a New Oral GH Secretagogue, NN703. Eur. J. Endocrinol. 1999, 141, 180-189.
16. Bergsma, D. J.; Ellis, C.; Kumar, C.; Nuthulaganti, P.; Kersten, H.; Elshourbagy, N.; Griffin, E.; Stadel, J. M.; Aiyar, N. Cloning and Characterization of A Human Angiotensin-Ii Type-1 Receptor. Biochem. Biophys. Res. Commun. 1992, 183, 989-995.
17. Dean, D. C.; Nargund, R. P.; Pong, S. S.; Chaung, L. Y. P.; Griffin, P.; Melillo, D. G.; Ellsworth, R. L.; VanDerPloeg, L. H. T.; Patchett, A. A.; Smith, R. G. Development of a High Specific Activity Sulfur-35-Labeled Sulfonamide Radioligand That Allowed the Identification of a New Growth Hormone Secretagogue Receptor. J. Med. Chem. 1996, 39, 1767-1770.
18. Devita, R. J.; Bochis, R.; Frontier, A. J.; Kotliar, A.; Fisher, M. H.; Schoen, W. R.; Wyvratt, M. J.; Cheng, K.; Chan, W. W. S.; Butler, B.; Jacks, T. M.; Hickey, G. J.; Schleim, K. D.; Leung, K.; Chen, Z. S.; Chiu, S. H. L.; Feeney, W. P.; Cunningham, P. K.; Smith, R. G. A Potent, Orally Bioavailable Benzazepinone Growth Hormone Secretagogue. J. Med. Chem. 1998, 41, 1716-1728.
19. Each residue is numbered according to the Ballesteros-Weinstein two digit representation, whereby the first digit is the transmembrane helix number (I to VII) under consideration followed by the sequential order of the residue position in that helix relative to the most conserved residue in the helix which is given number 50. With residues in one particular receptor the sequence number is given followed by the Ballesteros-Weinstein numbering in parentheses.
20. Yang, L. H.; Morriello, G.; Prendergast, K.; Cheng, K.; Jacks, T.; Chan, W. W. S.; Schleim, K. D.; Smith, R. G.; Patchett, A. A. Potent 3-Spiropiperidine Growth Hormone Secretagogues. Bioorg. Med. Chem. Lett. 1998, 8, 107-112.
21. Tata, J. R.; Lu, Z. J.; Jacks, T. M.; Schleim, K. D.; Cheng, K.; Wei, L. T.; Chan, W. W. S.; Butler, B.; Tsou, N.; Leung, K.; Chiu, S. H. L.; Hickey, G. ; Smith, R. G.; Patchett, A. A. The Design and Synthesis of Orally Active Short Duration Spiroindane Growth Hormone Secretagogues. Bioorg. Med. Chem. Lett. 1997, 7, 2319-2324.
22. Tata, J. R.; Nargund, R. P.; Murphy, M. M.; Johnston, D. B. R.; Patchett, A. A.; Cheng, K.; Wei, L.; Chan, W. W. S.; Butler, B.; Jacks, T. M.; Hickey, G.; Smith, R. The Synthesis and Activity of Spiroindane Growth Hormone Secretagogues. Bioorg. Med. Chem. Lett. 1997, 7, 663-668.
23. Chen, M. H.; Pollard, P. P.; Patchett, A. A. Synthesis and Biological Activities of Spiroheterocyclic Growth Hormone Secretagogues. Bioorg. Med. Chem. Lett. 1999, 9, 1261-1266.
24. Chen, M. H.; Steiner, M. G.; Patchett, A. A.; Cheng, K.; Wei, L. T.; Chan, W. W. S.; Butler, B.; Jacks, T. M.; Smith, R. G. Analogues of the Orally Active Growth Hormone Secretagogue L-162,752. Bioorg. Med. Chem. Lett. 1996, 6, 2163-2168.
25. Feighner, S. D.; Howard, A. D.; Prendergast, K.; Palyha, O. C.; Hreniuk, D. L.; Nargund, R.; Underwood, D.; Tata, J. R.; Dean, D. C.; Tan, C. P.; McKee, K. K.; Woods, J. W.; Patchett, A. A.; Smith, R. G.; Van der Ploeg, L. H. T. Structural Requirements for the Activation of the Human Growth Hormone Secretagogue Receptor by Peptide and Nonpeptide Secretagogues. Mol. Endocrinol. 1998, 12, 137-145.
26. Yanagisawa, H.; Amemiya, Y.; Kanazaki, T.; Shimoji, Y.; Fujimoto, K.; Kitahara, Y.; Sada, T.; Mizuno, M.; Ikeda, M.; Miyamoto, S.; Furukawa, Y.; Koike, H. Nonpeptide Angiotensin II Receptor Antagonists: Synthesis, Biological Activities, and Structure-Activity Relationships of Imidazole-5-Carboxylic Acids Bearing Alkyl, Alkenyl, and Hydroxyalkyl Substituents at the 4-Position and Their Related Compounds. J. Med. Chem. 1996, 39, 323-338.
27. Dascal, D.; Nirula, V.; Lawus, K.; Yoo, S. E.; Walsh, T. F.; Sandberg, K. Shared Determinants of Receptor Binding for Subtype Selective, and Dual Endothelin-Angiotensin Antagonists on the AT(1) Angiotensin II Receptor. FEBS Lett. 1998, 423, 15-18.
28. Ji, H.; Leung, M.; Zhang, Y.; Catt, K. J.; Sandberg, K. Differential Structural Requirements for Specific Binding of Nonpeptide and Peptide Antagonists to the At(1) Angiotensin Receptor - Identification of Amino-Acid-Residues That Determine Binding of the Antihypertensive Drug Losartan. J. Biol. Chem. 1994, 269, 16533-16536.
29. Noda, K.; Saad, Y.; Kinoshita, A.; Boyle, T. P.; Graham, R. M.; Husain, A.; Karnik, S. S. Tetrazole and Carboxylate Groups of Angiotensin Receptor Antagonists Bind to the Same Subsite by Different Mechanisms. J. Biol. Chem. 1995, 270, 2284-2289.
30. Hunyady, L.; Ji, H.; Jagadeesh, G.; Zhang, M.; Gaborik, Z.; Mihalik, B.; Catt, K. J. Dependence of at(1) Angiotensin Receptor Function on Adjacent Asparagine Residues in the 7th Transmembrane Helix. Mol. Pharm. 1998, 54, 427-434.
31. Schambye, H. T.; Hjorth, S. A.; Bergsma, D. J.; Sathe, G.; Schwartz, T. W. Differentiation Between Binding-Sites for Angiotensin-Ii and Nonpeptide Antagonists on the Angiotensin-Ii Type-1 Receptors. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7046-7050.
32. Devita, R. J.; Schoen, W. R.; Fisher, M. H.; Frontier, A. J.; Pisano, J. M.; Wyvratt, M. J.; Cheng, K.; Chan, W. W. S.; Butler, B. S.; Hickey, G. J.; Jacks, T. M.; Smith, R. G. Benzolactam Growth-Hormone Secretagogues - Carboxamides As Replacements for the 2′-Tetrazole Moiety of L-692,429. Bioorg. Med. Chem. Lett. 1994, 4, 2249-2254.
33. Ankersen, M.; Peschke, B.; Hansen, B. S.; Hansen, T. K. Investigation of Bioisosters of the Growth Hormone Secretagogue L-692,429. Bioorg. Med. Chem. Lett. 1997, 7, 1293-1298.
34. Schoen, W. R.; Ok, D.; Devita, R. J.; Pisano, J. M.; Hodges, P.; Cheng, K.; Chan, W. W. S.; Butler, B. S.; Smith, R. G.; Wyvratt, M. J.; Fisher, M. H. Structure-Activity-Relationships in the Amino-Acid Side-Chain of L-692,429. Bioorg. Med. Chem. Lett. 1994, 4, 1117-1122.
35. Mason, J. S.; Morize, I.; Menard, P. R.; Cheney, D. L.; Hulme, C.; Labaudiniere, R. F. New 4-Point Pharmacophore Method for Molecular Similarity and Diversity Applications: Overview of the Method and Applications, Including a Novel Approach to the Design of Combinatorial Libraries Containing Privileged Substructures. J. Med. Chem. 1999, 42, 3251-3264.
36. Gether, U. Uncovering Molecular Mechanisms Involved in Activation of G Protein-Coupled Receptors. Endocr. Rev. 2000, 21, 90-113.
37. Bissantz, C.; Bernard, P.; Hibert, M.; Rognan, D. Protein-Based Virtual Screening of Chemical Databases. II. Are Homology Models of G-Protein Coupled Receptors Suitable Targets? Proteins-Struct. Funct. Genet. 2003, 50, 5-25.
38. Gouldson, P.; Kidley, N. J.; Bywater, R. P.; Psaroudakis, G.; Brooks, H. D.; Diaz, C.; Shire, D.; Reynolds, C. A. Towards the Active Conformations of Rhopdopsin and the Beta2-Adrenergic Receptor. Proteins-Struct. Funct. Genet. 2004, in press.
39. Donnelly, D.; Overington, J. P.; Ruffle, S. V.; Nugent, J. H. A.; Blundell, T. L. Modeling Alpha-Helical Transmembrane Domains - the Calculation and Use of Substitution Tables for Lipid-Facing Residues. Protein Sci. 1993, 2, 55-70.
40. Sheikh, S. P.; Vilardarga, J. P.; Baranski, T. J.; Lichtarge, O.; Iiri, T.; Meng, E. C.; Nissenson, R. A.; Bourne, H. R. Similar Structures and Shared Switch Mechanisms of the Beta(2)-Adrenoceptor and the Parathyroid Hormone Receptor - Zn(II) Bridges Between Helices III and VI Block Activation. J. Biol. Chem. 1999, 274, 17033-17041.
41. Shi, L.; Javitch, J. A. The Binding Site of Aminergic G Protein-Coupled Receptors: The Transmembrane Segments and Second Extracellular Loop. Annu. Rev. Pharmacol. Toxicol. 2002, 42, 437-467.
42. Wong, P. C.; Price, W. A., Jr; Chiu, A. T.; Duncia, J. V.; Carini, D. J. ; Wexler, R. R.; Johnson, A. L.; Timmermans, P. B. M. W. Nonpeptide Angiotensin II Receptor Antagonists. XI. Pharmacology of EXP3174: An Active Metabolite of DuP 753, an Orally Active Antihypertensive Agent. J. Pharmacol. Exp. Ther. 1990, 255, 211-217.
43. Sinnokrot, M. O.; Valeev, E. F.; Sherrill, C. D. Estimates of the Ab Initio Limit for Pi-Pi Interactions: The Benzene Dimer. J. Am. Chem. Soc. 2002, 124, 10887-10893.
44. Perlman, S.; CostaNeto, C. M.; Miyakawa, A. A.; Schambye, H. T.; Hjorth, S. A.; Paiva, A. C. M.; Rivero, R. A.; Greenlee, W. J.; Schwartz, T. W. Dual Agonistic and Antagonistic Property of Nonpeptide Angiotensin AT(1) Ligands: Susceptibility to Receptor Mutations. Mol. Pharm. 1997, 51, 301-311.
45. Chakravarty, P. K.; Naylor, E. M.; Ransom, R. W. 1993, Patent No. US5204354.
46. Horn, F.; Vriend, G.; Cohen, F. E. Collecting and Harvesting Biological Data: the GPCRDB and NucleaRDB Information Systems. Nucleic Acids Res. 2001, 29, 346-349.
47. Rost, B.; Casadio, R.; Fariselli, P.; Sander, C. Transmembrane Helices Predicted at 95-Percent Accuracy. Protein Sci. 1995, 4, 521-533.
48. Vriend, G. What If - A Molecular Modeling and Drug Design Program. J. Mol. Graphics 1990, 8, 52.
49. Sali, A.; Blundell, T. L. Comparative Protein Modeling by Satisfaction of Spatial Restraints. J. Mol. Biol. 1993, 234, 779-815.
50. Halgren, T. A. Maximally Diagonal Force-Constants in Dependent Angle-Bending Coordinates 0.2. Implications for the Design of Empirical Force- Fields. J. Am. Chem. Soc. 1990, 112, 4710-4723.