Proposal of a new binding orientation for non-peptide AT1 antagonists: Homology modeling, docking and three-dimensional quantitative structure - Activity relationship analysis

Journal of Medicinal Chemistry

Volumn 49, Issue 14, 2006, Pages 4305-4316

  Tuccinardi, Tiziano ^a   Calderone, Vincenzo ^a   Rapposelli, Simona ^a   Martinelli, Adriano ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTYL 4 CHLORO 1 [[2' (1H TETRAZOL 5 YL) 4 BIPHENYLYL]METHYL] 5 IMIDAZOLECARBOXYLIC ACID; ANGIOTENSIN ANTAGONIST; CANDESARTAN; LOSARTAN; PEPTIDE; RHODOPSIN; VALSARTAN;

ALPHA HELIX; ARTICLE; BLOOD PRESSURE REGULATION; DRUG EFFECT; MODEL; MOLECULAR DYNAMICS; NONHUMAN; PEPTIDE ANALYSIS; PHOSPHOLIPID BILAYER; PROTEIN BINDING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RELIABILITY; RENIN ANGIOTENSIN ALDOSTERONE SYSTEM; SEQUENCE HOMOLOGY; SITE DIRECTED MUTAGENESIS;

AMINO ACID SEQUENCE; ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKERS; ANIMALS; CATTLE; CRYSTALLOGRAPHY, X-RAY; IMIDAZOLES; LIPID BILAYERS; LOSARTAN; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTATION; PHOSPHOLIPIDS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, ANGIOTENSIN, TYPE 1; RHODOPSIN; SEQUENCE HOMOLOGY, AMINO ACID; TETRAZOLES;

EID: 33745844039     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060338p     Document Type: Article

References (55)

1. Juillerat-Jeanneret, L.; Celerier, J.; Chapuis Bernasconi, C.; Nguyen, G.; Wostl, W.; Maerki, H. P.; Janzer, R. C.; Corvol, P.; Gasc, J. M. Renin and angiotensinogen expression and functions in growth and apoptosis of human glioblastoma. Br. J. Cancer 2004, 90, 1059-1068.
2. Fogarty, D. J.; Sanchez-Gomez, M. V.; Matute, C. Multiple angiotensin receptor subtypes in normal and tumor astrocytes in vitro. Glia 2002, 39, 304-313.
3. Henrion, D.; Kubis, N.; Levy, B. I. Physiological and pathophysiological functions of the AT(2) subtype receptor of angiotensin II: from large arteries to the microcirculation. Hypertension 2001, 38, 1150-1157.
4. Weber, M. A. Angiotensin II receptor blockers and cardiovascular outcomes: what does the future hold? JRAAS 2003, 4, 62-73.
5. Manohar, P.; Pina, I. L. Therapeutic role of angiotensin II receptor blockers in the treatment of heart failure. Mayo Clin. Proc. 2003, 78, 334-338.
6. Norris, K.; Vaughn, C. The role of renin-angiotensin-aldosterone system inhibition in chronic kidney disease. Exp. Rev. Cardiovasc. Ther. 2003, 1, 51-63.
7. Mimran, A.; Ribstein, J. Angiotensin receptor blockers: pharmacology and clinical significance. J. Am. Soc. Nephrol. 1999, S12, S273-S277.
8. Panek, R. L.; Lu, G. H.; Overhiser, R. W.; Major, T. C.; Hodges, J. C.; Taylor, D. G. Functional studies but not receptor binding can distinguish surmountable from insurmountable AT1 antagonism. J. Pharmacol. Exp. Ther. 1995, 273, 753-761.
9. Timmermans, P. B. Pharmacological properties of angiotensin II receptor antagonists. Can. J. Cardiol. 1999, 15 (Suppl F), 26F-28F.
10. De Gasparo, M.; Catt, K. J.; Inagami, T.; Wright, J. W.; Unger, T. International union of pharmacology. XXIII. The angiotensin II receptors. Pharmacol. Rev. 2000, 52, 415-472.
11. Okada, T.; Sugihara, M.; Bondar, A. N.; Elstner, M.; Entel, P.; Buss, V. The retinal conformation and its environment in rhodopsin in light of a new 2.2 Å crystal structure. J. Mol. Biol. 2004, 342, 571-583.
12. Baldwin, J. M.; Schertler, G. F.; Unger, V. M. An alpha-carbon template for the transmembrane helices in the rhodopsin family of G-protein-coupled receptors. J. Mol. Biol. 1997, 272, 144-164.
13. Fiser, A.; Do, R. K.; Sali, A. Modeling of loops in protein structures. Protein Sci. 2000, 9, 1753-1773.
14. Laskowski, R. A.; MacArthur, M. W.; Moss, D. S.; Thorton, J. M. PROCHECK: a program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 1993, 26, 283-291.
15. 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.
16. Ji, H.; Leung, M.; Zhang, Y.; Catt, K. J.; Sandberg, K. Differential structural requirements for specific binding of nonpeptide and peptide antagonists to the AT1 angiotensin receptor. Identification of amino acid residues that determine binding of the antihypertensive drug losartan. J. Biol. Chem. 1994, 269, 16533-16536.
17. Takezako, T.; Gogonea, C.; Saad, Y.; Noda, K.; Karnik, S. S. "Network leaning" as a mechanism of insurmountable antagonism of the angiotensin II type 1 receptor by non-peptide antagonists. J. Biol. Chem. 2004, 279, 15248-15257.
18. Balmforth, A. J.; Lee, A. J.; Warburton, P.; Donnelly, D.; Ball, S. G. The conformational change responsible for AT1 receptor activation is dependent upon two juxtaposed asparagine residues on transmembrane helices III and VII. J. Biol. Chem. 1997, 272, 4245-4251.
19. Hines, J.; Fluharty, S. J.; Yee, D. K. Structural determinants for the activation mechanism of the angiotensin II type 1 receptor differ for phosphoinositide hydrolysis and mitogen-activated protein kinase pathways. Biochem. Pharmacol. 2003, 66, 251-262.
20. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a lamarckian genetic algorithm and empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
21. Zoumpoulakis, P.; Daliani, I.; Zervou, M.; Kyrikou, I.; Siapi, E.; Lamprinidis, G.; Mikros, E.; Mavromoustakos, T. Losartan's molecular basis of interaction with membranes and AT1 receptor. Chem. Phys. Lipids 2003, 125, 13-25.
22. Mehler, E. L.; Periole, X.; Hassan, S. A.; Weinstein, H. Key issues in the computational simulation of GPCR function: representation of loop domains. J. Comput.-Aided Mol. Des. 2002, 16, 841-853.
23. Mavromoustakos, T.; Daliani, I.; Matsoukas, J. The application for biophysical methods to study drug: membrane interactions. In Bioactive Peptides in Drug Discovery and Design: Medical Aspects; Matsoukas, J., Mavromoustakos, T., Eds.; Biomedical and Health Research, Vol. 22: IOS Press-Ohmsha: Amsterdam, 1999; pp 13-24.
24. Theodoropoulou, E.; Marsh, D. Interactions of angiotensin II non-peptide AT(1) antagonist losartan with phospholipid membranes studied by combined use of differential scanning calorimetry and electron spin resonance spectroscopy. Biochim. Biophys. Acta 1999, 1461, 135-146.
25. Boucard, A. A.; Roy, M.; Beaulieu, M. E.; Lavigne, P.; Escher, E.; Guillemette, G.; Leduc, R. Constitutive activation of the angiotensin II type 1 receptor alters the spatial proximity of transmembrane 7 to the ligand-binding pocket. J. Biol. Chem. 2003, 278, 36628-36636.
26. Martin, S. S.; Boucard, A. A.; Clement, M.; Escher, E.; Leduc, R.; Guillemette, G. Analysis of the third transmembrane domain of the human type 1 angiotensin II receptor by cysteine scanning mutagenesis. J. Biol. Chem. 2004, 279, 51415-51423.
27. Clement, M.; Martin, S. S.; Beaulieu, M. E.; Chamberland, C.; Lavigne, P.; Leduc, R.; Guillemette, G.; Escher, E. Determining the environment of the ligand binding pocket of the human angiotensin II type I (hAT1) receptor using the methionine proximity assay. J. Biol. Chem. 2005, 280, 27121-27129.
28. Doan, T. N.; Ali, M. S.; Bernstein, K. E. Tyrosine kinase activation by the angiotensin II receptor in the absence of calcium signaling. J. Biol. Chem. 2001, 276, 20954-20958.
29. Le, M. T.; Vanderheyden, P. M.; Szaszak, M.; Hunyady, L.; Kersemans, V.; Vauquelin, G. Peptide and nonpeptide antagonist interaction with constitutively active human AT1 receptors. Biochem. Pharmacol. 2003, 65, 1329-1338.
30. Hunyady, L.; Ji, H.; Jagadeesh, G.; Zhang, M.; Gaborik, Z.; Mihalik, B.; Catt, K. J. Dependence of AT1 angiotensin receptor function on adjacent asparagine residues in the seventh transmembrane helix. Mol. Pharmacol. 1998, 54, 427-434.
31. Monnot, C.; Bihoreau, C.;Conchon, S.; Curnow, K. M.; Corvol, P.; Clauser, E. Polar residues in the transmembrane domains of the type I angiotensin II receptor are required for binding and coupling. Reconstitution of the binding site by coexpression of two deficient mutants. J. Biol. Chem. 1996, 271, 1507-1513.
32. Fierens, F. L.; Vanderheyden, P. M.; Gaborik, Z.; Minh, T. L.; Backer, J. P.; Hunyady, L.; Ijzerman, A.; Vauquelin, G. Lys(199) mutation of the human angiotensin type 1 receptor differentially affects the binding of surmountable and insurmountable non-peptide antagonists. JRAAS 2000, 3, 283-288.
33. Pandya, T.; Pandey, S. K.; Tiwari, M.; Chaturvedi, S. C.; Saxena, A. K. 3-D-QSAR studies of triazolinone based balanced AT1/AT2 receptor antagonists. Bioorg. Med. Chem. 2001, 9, 291-300.
34. Kurup, A.; Gary, R.; Carini, D. J.; Hansch, C. Comparative QSAR: Angiotensin II antagonists. Chem. Rev. 2001, 101, 2727-2750.
35. Krovat, E. M.; Langer, T. Non-peptide angiotensin II receptor antagonists: chemical feature based pharmacophore identification. J. Med. Chem. 2003, 46, 716-726.
36. Datar, P. A.; Desai, P. V.; Coutinho, E. C. A 3D-QSAR of angiotensin II (AT1) receptor antagonists based on receptor surface analysis. J. Chem. Inf. Comput. Sci. 2004, 44, 210-220.
37. Cappelli, A.; Pericot Mohr, Gl. G.; Gallelli, A.; Rizzo, M.; Anzini, M.; Vomero, S.; Mennuni, L.; Ferrari, F.; Makovec, F.; Menziani, M. C.; De Benedetti, P. G.; Giorgi, G. Design, synthesis, structural studies, biological evaluation, and computational simulations of novel potent AT(1) angiotensin II receptor antagonists based on the 4-phenylquinoline structure. J. Med. Chem. 2004, 47, 2574-2586.
38. Yoo, S. E.; Kim, S. K.; Lee, S. H.; Yi, K. Y.; Lee, D. W. A comparative molecular field analysis and molecular modelling studies on pyridylimidazole type of angiotensin II antagonists. Bioorg. Med. Chem. 1999, 7, 2971-2976.
39. Belvisi, L.; Bravi, G.; Catalano, G.; Mabilia, M.; Salimbeni, A.; Scolastico, C. A 3D QSAR CoMFA study of non-peptide angiotensin II receptor antagonists. J. Comput.-Aided Mol. Des. 1996, 10, 567-582.
40. Datar, P.; Desai, P.; Coutinho, E.; Iyer, K. CoMFA and CoMSIA studies of angiotensin (AT1) receptor antagonists. J. Mol. Model. 2002, 8, 290-301.
41. Duncia, J. V.; Chiu, A. T.; Carini, D. J.; Gregory, G. B.; Johnson, A. L.; Price, W. A.; Wells, G. J.; Wong, P. C.; Calabrese, J. C.; Timmermans, P. B. The discovery of potent nonpeptide angiotensin II receptor antagonists: a new class of potent antihypertensives. J. Med. Chem. 1990, 33, 1312-1329.
42. Carini, D. J.; Duncia, J. V.; Johnson, A. L.; Chiu, A. T.; Price, W. A1; Wong, P. C.; Timmermans, P. B. Nonpeptide angiotensin II receptor antagonists: N-[(benzyloxy)benzyl]imidazoles and related compounds as potent antihypertensives. J. Med. Chem. 1990, 33, 1330-1336.
43. Wong, P. C.; Price, W. A., Jr; Chiu, A. T.; Carini, D. J.; Duncia, J. V.; Johnson, A. L.; Wexler, R. R.; Timmermans, P. B. Nonpeptide angiotensin II receptor antagonists. Studies with EXP9270 and DuP 753. Hypertension 1990, 15, 823-834.
44. Carini, D. J.; Duncia, J. V.; Aldrich, P. E.; Chiu, A. T.; Johnson, A. L.; Pierce, M. E.; Price, W. A.; Santella, J. B., 3rd; Wells, G. J.; Wexler, R. R.; et al. Nonpeptide angiotensin II receptor antagonists: the discovery of a series of N-(biphenylylmethyl)imidazoles as potent, orally active antihypertensives. J. Med. Chem. 1991, 34, 2525-2547.
45. GOLPE 4.5. Multivariate Infometric Analysis Srl., Viale dei Castagni 16, Perugia, Italy, 1999.
46. Ballesteros, J. A.; Weinstein, H. W. Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G-protein coupled receptors. Methods Neurosci. 1995, 23, 366-428.
47. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The Protein Data Bank. Nucleic Acids Res. 2000, 28, 235-242.
48. Gasteiger, E.; Gattiker, A.; Hoogland, C.; Ivanyi, I.; Appel, R. D.; Bairoch, A. ExPASy: the proteomics server for in-depth protein knowledge and analysis. Nucleic Acids Res. 2003, 31, 3784-3788.
49. Thompson, J. D.; Higgins, D. G.; Gibson, T. J. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 1994, 22, 4673-4680.
50. Heerding, J. N.; Hines, J.; Fluharty, S. J.; Yee, D. K. Identification and function of disulfide bridges in the extracellular domains of the angiotensin II type 2 receptor. Biochemistry 2001, 40, 8369-8377.
51. Macromodel, ver. 8.5; Schrödinger Inc.: Portland, OR, 1999.
52. Case, D. A.; Darden, T. A.; Cheatham, T. E., III; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Merz, K. M.; Wang, B.; Pearlman, D. A.; Crowley, M.; Brozell, S.; Tsui, V.; Gohlke, H.; Mongan, J.; Hornak, V.; Cui, G.; Beroza, P.; Schafmeister, C.; Caldwell, J. W.; Ross, W. S.; Kollinan, P. A. AMBER 8; University of California, San Francisco: 2004.
53. Darden, T.; Darrin, Y.; Pedersen, L. Particle mesh Ewald: An N· log(N) method for Ewald sums in large systems. J. Chem. Phys. 1993, 98, 10089-10092.
54. Cruciani, G.; Goodford, P. Copyright Molecular Discovery Ltd. 2001-2003 GREATER graphical interface for GRID version, 1.1.7 GRIB, UPF/IMIM, Barcelona (Spain) http://www.moldiscovery.com.
55. Pastor, M.; Cruciani, G.; Clementi, S. Smart region definition: a new way to improve the predictive ability and interpretability of three-dimensional quantitative structure-activity relationships. J. Med. Chem. 1997, 40, 1455-1464.