Three-dimensional models for β-adrenergic receptor complexes with agonists and antagonists

Journal of Medicinal Chemistry

Volumn 46, Issue 21, 2003, Pages 4450-4462

  Furse, Kristina E ^a   Lybrand, Terry P ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 ISOPROPYLAMINO 1 (7 METHYL 4 INDANYLOXY) 2 BUTANOL; 4 (BROMOACETAMIDYL)BENZYLCARAZOLOL; [[3 [2 [[2 (3 CHLOROPHENYL) 2 HYDROXYETHYL]AMINO]PROPYL] 1H INDOL 7 YL]OXY]ACETIC ACID; ADRENALIN; AJ 9677; AMINOFLISOPOL; BETA ADRENERGIC RECEPTOR; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; BETA ADRENERGIC RECEPTOR STIMULATING AGENT; CARAZOLOL; CARMOTEROL; ISOPRENALINE; PROPRANOLOL; RHODOPSIN; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG RECEPTOR BINDING; DRUG STRUCTURE; ISOMER; MOLECULAR MODEL; RECEPTOR SENSITIVITY;

ADRENERGIC BETA-AGONISTS; ADRENERGIC BETA-ANTAGONISTS; ANIMALS; BINDING SITES; CATTLE; DRUG DESIGN; EPINEPHRINE; HYDROGEN BONDING; ISOPROTERENOL; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROPANOLAMINES; RECEPTORS, ADRENERGIC, BETA; RHODOPSIN; STEREOISOMERISM;

EID: 0141992805     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0301437     Document Type: Article

References (60)

1. Bikker, J. A.; Trump-Kallmeyer, S.; Humblet, C. G-protein coupled receptors: Models, mutagenesis, and drug design. J. Med. Chem. 1998, 41, 2911-2927.
2. Gershengorn, M. C.; Osman, R. Minireview: insights into G protein-coupled receptor function using molecular models. Endocrinology 2001, 142, 2-10.
3. Henderson, R.; Baldwin, J. M.; Ceska, T. A.; Zemlin, F.; Beckmann, E.; Downing, K. H. Model for the structure of bacteriorhodopsin based on high-resolution electron cryomicroscopy. J. Mol. Biol. 1995, 213, 899-929.
4. Pebay-Peyroula, E.; Rummel, G.; Rosenbusch, J. P.; Landau, E. M. X-ray structure of bacteriorhodopsin at 2.5 angstroms from microcrystals grown in lipidic cubic phases. Science 1997, 277, 1676-1681.
5. Soppa, J. Two hypotheses-one answer: Sequence comparison does not support an evolutionary link between halobacterial retinal proteins including bacteriorhodopsin and eukaryotic G-protein-coupled receptors. FEBS Lett. 1994, 342, 7-11.
6. 2 adrenergic receptor. J. Med. Chem. 1996, 39, 4406-4420.
7. Palczewski, K.; Kumasaka, T.; Hori, T.; Behnke, C. A.; Motoshima, H.; Fox, B. A.; Trong, I. L.; 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.
8. 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.
9. Archer, E.; Maigret, B.; Escrieut, C.; Pradayrol, L.; Fourmy, D. Rhodopsin crystal: New template yielding realistic models of G-protein-coupled receptors? Trends Pharmacol. Sci. 2003, 24, 36-40.
10. 2A receptor derived from an in silico activated G-protein coupled receptor. J. Comput.-Aided Mol. Des. 2002, 16, 511-520.
11. Ding, X.-Q.; Pinon, D. I.; Furse, K. E.; Lybrand, T. P.; Miller, L. J. Refinement of the conformation of a critical region of charge-charge interaction between cholecystokinin and its receptor. Mol. Pharmacol. 2002, 61, 1041-1052.
12. Okada, T.; Ernst, O. P.; Palczewski, K.; Hofmann, K. P. Activation of rhodopsin: new insights from structural and biochemical studies. Trends Biochem. Sci. 2001, 26, 318-324.
13. Farrens, D. L.; Altenbach, C.; Yang, K.; Hubbell, W. L.; Khorana, H. G. Requirement of rigid-body motion of transmembrane helices for light activation ofrhodopsin. Science 1996, 274, 768-770.
14. Dunham, T. D.; Farrens, D. L. Conformational changes in rhodopsin- Movement of helix F detected by site-specific chemical labeling and fluorescence spectroscopy. J. Biol. Chem. 1999, 274, 1683-1690.
15. Altenbach, C.; Cai, K. W.; Klein-Seetharaman, J.; Khorana, H. G.; Hubbell, W. L. Structure and function in rhodopsin: Mapping light-dependent changes in the distance between residue 65 in helix TM1 and residues in the sequence 306-319 at the cytoplasmic end of helix TM7 and in helix H8. Biochemistry 2001, 40, 15483-15492.
16. Ghanouni, P.; Gryczynski, Z.; Steenhuis, J. J.; Lee, T. W.; Farrens, D. L.; Lakowicz, J. R.; Kobilka, B. K. Functionally different agonists induce distrinct conformations in the G protein coupling domain of the beta(2) adrenergic receptor. J. Biol. Chem. 2001, 276, 24433-24436.
17. Peleg, G.; Ghanouni, P.; Kobilka, B. K.; Zare, R. N. Single-molecule spectroscopy of the beta(2) adrenergic receptor: Observation of conformational substates in a membrane protein. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 8469-8474.
18. Kenakin, T. Agonist-specific receptor conformations. Trends Pharm. Sci. 1997, 18, 416-417.
19. Unger, V. M.; Hargrave, P. A.; Baldwin, J. M.; Schertler, G. F. X. Arrangement of rhodopsin transmembrane α-helices. Nature 1997, 389, 203-206.
20. Dixon, R. A. F.; Sigal, I. S.; Strader, C. D. Structure-function analysis of the β-adrenergic receptor. Cold Spring Harbor Symp. Quantum Biol. 1988, 53, 487-497.
21. Strader, C. D.; Candelore, M. R.; Hill, W. S.; Sigal, I. S.; Dixon, R. A. F. Identification of Two Serine Residues Involved in Agonist Activation of the β-Adrenergic Receptor. J. Biol. Chem. 1989, 264, 13572-13578.
22. Wu, Z.; Thiriot, D. S.; Ruoho, A. E. Tyr199 in transmembrane domain 5 of the b2-adrenergic receptor interacts directly with the pharmacophore of a unique fluorenone-based antagonist. Biochem. J. 2001, 354, 485-491.
23. 2-adrenergic Receptor. Biochemistry 1988, 27, 1813-1817.
24. de Souza, C. J.; Burkey, B. F. Beta(3)-adrenoceptor agonists as anti-diabetic and anti-obesity drugs in humans. Curr. Pharmceut. Des. 2001, 7, 1433-1449.
25. 2 adrenergic receptor protein based on computer modeling studies. J. Mol. Biol. 1992, 225, 859-871.
26. Sansom, M. S. P.; Weinstein, H. Hinges, swivels, and switches: The role of prolines in signaling via transmembrane alpha-helices. Trends Pharmacol. Sci. 2000, 21, 445-451.
27. Sankararamakrishnan, R.; Vishveshwara, S. Geometry of proline-containing alpha-helices in proteins. Int. J. Pept. Protein Res. 1992, 39, 356-363.
28. Liapakis, G.; Ballesteros, J. A.; Papachristou, S.; Chan, W. C.; Chen, X.; Javitch, J. A. The forgotten serine. A critical role for Ser-203 (5.42) in ligand binding to and activation of the b2-adrenergic receptor. J. Biol. Chem. 2000, 275, 37779-37788.
29. Dohlman, H. G.; Caron, M. G.; DeBlasi, A.; Frielle, T.; Lefkowitz, R. J. Role of Extracellular Disulfide-Bonded Cysteines in the Ligand Binding Function of the Beta(2)-Adrenergic Receptor. Biochemistry 1990, 29, 2335-2342.
30. Noda, K.; Saad, Y.; Graham, R. M.; Karnik, S. S. The high affinity state of the beta-2 adrenergic receptor requires unique interaction between conserved and non-conserved extracellular loop cysteines. J. Bol. Chem. 1994, 269, 6743-6752.
31. Visiers, I.; Ballesteros, J. A.; Weinstein, H. Three-dimensional representations of G protein-coupled receptor structures and mechanisms. Methods Enzymol. 2001, 343, 329-371.
32. Zuurmond H. M.; Hessling J.; Bluml K.; Lohse M.; Ijzerman A. P. Study of interaction between agonists and Asn293 in helix VI of human beta(2)-adrenergic receptor. Mol. Pharmacol. 1999, 56, 909-16.
33. Suryanarayana, S.; Kobilka, B. K. Amino acid substitutions at position 312 in the seventh hydrophobic segment of the b2-adrenergic receptor modify ligand-binding specificity. Mol. Pharmacol. 1993, 44, 111-114.
34. Kuipers, W.; Link, R.; Standaar, P. J.; Stoit, A. R.; van Wijngaarden, I.; Leurs, R.; Ijzerman, A. P. Study of the interaction between aryloxypropanolamines and Asn 386 in helix VII of the human 5-hydroxytryptaminelA receptor. Mol. Pharmacol. 1997, 51, 889-896.
35. Mizobe, T.; Maze, M.; Lam, V.; Suryanarayana, S.; Kobilka, B. K. Arrangement of transmembrane domains in adrenergic receptors. Similarity to bacteriorhodopsin. J. Biol. Chem. 1996, 271, 2387-2389.
36. Azzi, M.; Piñeyro, G.; Pontier, S.; Parent, S.; Ansanay, H.; Bouvier, M. Allosteric effects of G protein overexpression on the binding of β-adrenergic ligands with distinct inverse efficacies. Mol. Pharmacol. 2001, 60, 999-1007.
37. Kikkawa, H.; Naito, K.; Ikezawa, K. Tracheal relaxing effects and beta2-selectivity of TA-2005, a newly developed bronchodilating agent, in isolated guinea pig tissues. Jpn. J. Pharm. 1991, 57, 175-85.
38. 2-selective agonists. Br. J. Pharmacol. 1997, 121, 1059-1064.
39. 2-selective agonist TA-2005. Mol. Pharmacol. 1998, 53, 128-134.
40. Blin, N.; Camoin, L.; Maigret, B.; Strosberg, D. A. Structural and conformational features determining selective signal transduction in the Beta(3)-adrenergic receptor. Mol. Pharmacol. 1993, 44, 1094-1104.
41. Kato, S.; Harada, H.; Fujii, A.; Kotai, O. Preparation of optically active indoles and their intermediates as antidiabetics and antiobesity agents. Jpn. Kokai Tokkyo Koho 1999, 13 pp.
42. Rao, V. R.; Oprian, D. D. Activating mutations of rhodopsin and other G protein-coupled receptors. Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 287-314.
43. Ghanouni, P.; Steenhuis, J. J.; Farrens, D. L.; Kobilka, B. K. Agonist-induced conformational changes in the G-protein-coupling domain of the β2 adrenergic receptor. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5997-6002.
44. Salamon, Z.; Hruby, V. J.; Tollin, G.; Cowell, S. Binding of agonists, antagonists, and inverse agonists to the human delta-opioid receptor produces distinctly different conformational states distinguishable by plasmon-waveguide resonance spectroscopy. J. Pept. Res. 2002, 60, 322-328.
45. Bower, M. J.; Cohen, F. E.; Dunbrack Jr., R. L. Prediction of protein side-chain rotamers from a backbone-dependent rotamer library: A new homology modeling tool. J. Mol. Biol. 1997, 267, 1268-1282.
46. Dunbrack Jr., R. L.; Karplus, M. Backbone-dependent rotamer library for proteins: Application to side-chain prediction. J. Mol. Biol. 1993, 230, 543-574.
47. Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheatham, T. E.; DeBolt, S.; Ferguson, D.; Seibel, G.; Kollman P. A. AMBER, a package of computer programs for applying molecular mechanics, normal mode analysis, molecular dynamics and free energy calculations to simulate the structural and energetic properties ofmolecules. Comput. Phys. Commun. 1995, 91, 1-41.
48. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A second generation force field for the simulation of proteins and nucleic acids. J. Am. Chem. Soc. 1995, 117, 5179-5197.
49. Laskowski, R. M. M.; Moss D.; Thornton, J. PROCHECK: A program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 1993, 26, 283-291.
50. Gregoret, L. M.; Cohen, F. E. Novel method for the rapid evaluation of packing in protein structures. J. Mol. Biol. 1990, 211, 959-74.
51. Swanson, E. PSSHOW, Version 2.4; Seattle, WA, 1995.
52. Molecular Operating Environment, 2000.02; Chemical Computing Group Inc.: Montreal, Quebec, Canada, 2000 (http://www.chemcomp.com).
53. Blaney, J. M.; Dixon, J. S. Distance geometry in molecular modeling. Rev. Comput. Chem. 1994, 5, 299-335.
54. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malic, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian98; Gaussian, Inc.: Pittsburgh, PA, 1998.
55. Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman P. A. A well-behaved electrostatic potential based method using charge restraints for determining atom-centered charges: The RESP model. J. Phys. Chem. 1993, 97, 10269-10280.
56. Callahan, T. J.; Swanson, E.; Lybrand, T. P. MD Display: An interactive graphics program for visualization of molecular dynamics trajectories. J. Mol. Graph. 1996, 14, 39-41.
57. Meng, E. C.; Soichet, B. M.; Kuntz, I. D. Automated docking with grid-based energy evaluation. J. Comput. Chem. 1992, 13, 505-524.
58. Livingstone, C. D.; Barton, G. J. Protein sequence alignments: A strategy for the hierarchical analysis of residue conservation. CABIOS 1993, 9, 745-756.
59. Sanner, M. F.; Olson, A. J.; Spehner, J.-C. Reduced surface: an efficient way to compute molecular surfaces. Biopolymers 1996, 38, 305-320.
60. DINO: Visualizing Structural Biology, 2001 (http://www.dino3d.org).