Structure-based drug design using GPCR homology modeling: Toward the discovery of novel selective CysLT2 antagonists

European Journal of Medicinal Chemistry

Volumn 62, Issue , 2013, Pages 754-763

  Dong, Xiaowu ^a   Zhao, Yanmei ^a   Huang, Xueqin ^b   Lin, Kana ^b   Chen, Jianzhong ^a   Wei, Erqing ^b   Liu, Tao ^a   Hu, Yongzhou ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY SCHOOL OF MEDICINE   (China)

Author keywords

CysLT2 antagonists; G protein coupled receptors; Homology model; Molecular docking; Structure based design

Indexed keywords

6 (4 CARBOXYPHENYLTHIO) 5 HYDROXY 7,9,11,14 ICOSATETRAENOIC ACID; CHALCONE DERIVATIVE; G PROTEIN COUPLED RECEPTOR; LEUKOTRIENE RECEPTOR; LEUKOTRIENE RECEPTOR BLOCKING AGENT; PEPTIDOLEUKOTRIENE 2 RECEPTOR; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BINDING SITE; CALCIUM CELL LEVEL; CONTROLLED STUDY; DRUG BINDING; DRUG DESIGN; HYDROGEN BOND; IC 50; MOLECULAR DOCKING; MOLECULAR DYNAMICS; PHYLOGENY; SIMULATION; WESTERN BLOTTING;

CHALCONES; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; HEK293 CELLS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RECEPTORS, LEUKOTRIENE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84876010057     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.01.041     Document Type: Article

References (43)

1. S. Poulin, C. Thompson, M. Thivierge, S. Veronneau, S. McMahon, C.M. Dubois, J. Stankova, and M. Rola-Pleszczynski Cysteinyl-leukotrienes induce vascular endothelial growth factor production in human monocytes and bronchial smooth muscle cells Clin. Exp. Allergy 41 2011 204 217
2. E. Mayatepek, and G.F. Hoffmann Leukotrienes: biosynthesis, metabolism, and pathophysiologic significance Pediatr. Res. 37 1995 1 9
3. K.F. Chung Leukotriene receptor antagonists and biosynthesis inhibitors: potential breakthrough in asthma therapy Eur. Respir. J. 8 1995 1203 1213
4. H.E. Claesson, and S.E. Dahlen Asthma and leukotrienes: antileukotrienes as novel anti-asthmatic drugs J. Intern. Med. 245 1999 205 227
5. R.A. Coleman, R.M. Eglen, R.L. Jones, S. Narumiya, T. Shimizu, W.L. Smith, S.E. Dahlen, J.M. Drazen, P.J. Gardiner, and W.T. Jackson Prostanoid and leukotriene receptors: a progress report from the IUPHAR working parties on classification and nomenclature Adv. Prostaglandin Thromboxane Leukot. Res. 23 1995 283 285
6. S.H. Yoo, S.H. Park, J.S. Song, K.H. Kang, C.S. Park, J.H. Yoo, B.W. Choi, and M.H. Hahn Clinical effects of pranlukast, an oral leukotriene receptor antagonist, in mild-to-moderate asthma: a 4 week randomized multicentre controlled trial Respirology 6 2001 15 21
7. G.L. Yu, E.Q. Wei, M.L. Wang, W.P. Zhang, S.H. Zhang, J.Q. Weng, L.S. Chu, S.H. Fang, Y. Zhou, Z. Chen, Q. Zhang, and L.H. Zhang Pranlukast, a cysteinyl leukotriene receptor-1 antagonist, protects against chronic ischemic brain injury and inhibits the glial scar formation in mice Brain Res. 1053 2005 116 125
8. S.L. Spector Management of asthma with zafirlukast. Clinical experience and tolerability profile Drugs 52 Suppl. 6 1996 36 46
9. V. Capra Molecular and functional aspects of human cysteinyl leukotriene receptors Pharmacol. Res. 50 2004 1 11
10. M. Back Functional characteristics of cysteinyl-leukotriene receptor subtypes Life Sci. 71 2002 611 622
11. H. Galczenski, J. Hutchinson, D.J. Figueroa, J. Scheigetz, R. Young, J.F. Evans, American Thoracic Society, in: 98th International Conference (May 2002, Atlanta) [D38] [Poster F4] Characterization of DUO-LT: A Novel Dual Cysteinyl Receptor Antagonist.
12. F. Wunder, H. Tinel, R. Kast, A. Geerts, E.M. Becker, P. Kolkhof, J. Hutter, J. Erguden, and M. Harter Pharmacological characterization of the first potent and selective antagonist at the cysteinyl leukotriene 2 (CysLT(2)) receptor Br. J. Pharmacol. 160 2010 399 409
13. S. Moro, F. Deflorian, G. Spalluto, G. Pastorin, B. Cacciari, S.K. Kim, and K.A. Jacobson Demystifying the three dimensional structure of G protein-coupled receptors (GPCRs) with the aid of molecular modeling Chem. Commun. (Camb) 2003 2949 2956
14. A.M. Van Rhee, B. Fischer, P.J. Van Galen, and K.A. Jacobson Modelling the P2Y purinoceptor using rhodopsin as template Drug Des. Discov. 13 1995 133 154
15. Q. Jiang, D. Guo, B.X. Lee, A.M. Van Rhee, Y.C. Kim, R.A. Nicholas, J.B. Schachter, T.K. Harden, and K.A. Jacobson A mutational analysis of residues essential for ligand recognition at the human P2Y1 receptor Mol. Pharmacol. 52 1997 499 507
16. L. Erb, R. Garrad, Y. Wang, T. Quinn, J.T. Turner, and G.A. Weisman Site-directed mutagenesis of P2U purinoceptors. Positively charged amino acids in transmembrane helices 6 and 7 affect agonist potency and specificity J. Biol. Chem. 270 1995 4185 4188
17. R. Fredriksson, M.C. Lagerstrom, L.G. Lundin, and H.B. Schioth The G-protein-coupled receptors in the human genome form five main families. Phylogenetic analysis, paralogon groups, and fingerprints Mol. Pharmacol. 63 2003 1256 1272
18. C. Parravicini, G. Ranghino, M.P. Abbracchio, and P. Fantucci GPR17: molecular modeling and dynamics studies of the 3-D structure and purinergic ligand binding features in comparison with P2Y receptors BMC Bioinform. 9 2008 263
19. I. Eberini, S. Daniele, C. Parravicini, C. Sensi, M.L. Trincavelli, C. Martini, and M.P. Abbracchio In silico identification of new ligands for GPR17: a promising therapeutic target for neurodegenerative diseases J. Comput. Aided Mol. Des. 25 2011 743 752
20. X. Dong, L. Wang, X. Huang, T. Liu, E. Wei, L. Du, B. Yang, and Y. Hu Pharmacophore identification, synthesis, and biological evaluation of carboxylated chalcone derivatives as CysLT1 antagonists Bioorg. Med. Chem. 18 2010 5519 5527
21. C.E. Heise, B.F. O'Dowd, D.J. Figueroa, N. Sawyer, T. Nguyen, D.S. Im, R. Stocco, J.N. Bellefeuille, M. Abramovitz, R. Cheng, D.L. Williams Jr., Z. Zeng, Q. Liu, L. Ma, M.K. Clements, N. Coulombe, Y. Liu, C.P. Austin, S.R. George, G.P. O'Neill, K.M. Metters, K.R. Lynch, and J.F. Evans Characterization of the human cysteinyl leukotriene 2 receptor J. Biol. Chem. 275 2000 30531 30536
22. J. Takasaki, M. Kamohara, M. Matsumoto, T. Saito, T. Sugimoto, T. Ohishi, H. Ishii, T. Ota, T. Nishikawa, Y. Kawai, Y. Masuho, T. Isogai, Y. Suzuki, S. Sugano, and K. Furuichi The molecular characterization and tissue distribution of the human cysteinyl leukotriene CysLT(2) receptor Biochem. Biophys. Res. Commun. 274 2000 316 322
23. E.A. Mellor, A. Maekawa, K.F. Austen, and J.A. Boyce Cysteinyl leukotriene receptor 1 is also a pyrimidinergic receptor and is expressed by human mast cells Proc. Natl. Acad. Sci. U.S.A. 98 2001 7964 7969
24. T. Okada, M. Sugihara, A.N. Bondar, M. Elstner, P. Entel, and V. Buss The retinal conformation and its environment in rhodopsin in light of a new 2.2 Å crystal structure J. Mol. Biol. 342 2004 571 583
25. J. Kyte, and R.F. Doolittle A simple method for displaying the hydropathic character of a protein J. Mol. Biol. 157 1982 105 132
26. B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, and M. Karplus CHARMM-a program for macromolecular energy, minimization, and dynamics calculations J. Comput. Chem. 4 1983 187 217
27. D.P. Tieleman, and H.J.C. Berendsen molecular dynamics simulations of a fully hydrated dipalmitoylphosphatidylcholine bilayer with different macroscopic boundary conditions and parameters J. Chem. Phys. 105 1996 4871 4880
28. D.P. Tieleman, S.J. Marrink, and H.J. Berendsen A computer perspective of membranes: molecular dynamics studies of lipid bilayer systems Biochim. Biophys. Acta 1331 1997 235 270
29. S. Jo, T. Kim, and W. Im Automated builder and database of protein/membrane complexes for molecular dynamics simulations PLoS One 2 2007 e880
30. C.M. Venkatachalam, X. Jiang, T. Oldfield, and M. Waldman LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites J. Mol. Graph. Model. 21 2003 289 307
31. T. Ahnfeldt, D. Gunzelmann, T. Loiseau, D. Hirsemann, J. Senker, G. Ferey, and N. Stock Synthesis and modification of a functionalized 3D open-framework structure with MIL-53 topology Inorg. Chem. 48 2009 3057 3064
32. R. Vijayalakshmi, V. Subramanian, and B.U. Nair A study of the interaction of Cr(III) complexes and their selective binding with B-DNA: a molecular modeling approach J. Biomol. Struct. Dyn. 19 2002 1063 1071
33. F. Horn, J. Weare, M.W. Beukers, S. Horsch, A. Bairoch, W. Chen, O. Edvardsen, F. Campagne, and G. Vriend GPCRDB: an information system for G protein-coupled receptors Nucleic Acids Res. 26 1998 275 279
34. F. Horn, E. Bettler, L. Oliveira, F. Campagne, F.E. Cohen, and G. Vriend GPCRDB information system for G protein-coupled receptors Nucleic Acids Res. 31 2003 294 297
35. D.T. Major, and B. Fischer Molecular recognition in purinergic receptors. 1. A comprehensive computational study of the h-P2Y(1)-receptor J. Med. Chem. 47 2004 4391 4404
36. S.S. Karnik, and H.G. Khorana Assembly of functional rhodopsin requires a disulfide bond between cysteine residues 110 and 187 J. Biol. Chem. 265 1990 17520 17524
37. K. Palczewski, T. Kumasaka, T. Hori, C.A. Behnke, H. Motoshima, B.A. Fox, I. Le Trong, D.C. Teller, T. Okada, R.E. Stenkamp, M. Yamamoto, and M. Miyano Crystal structure of rhodopsin: a G protein-coupled receptor Science 289 2000 739 745
38. C. Gerard, C. Mollereau, G. Vassart, and M. Parmentier Nucleotide sequence of a human cannabinoid receptor cDNA Nucleic Acids Res. 18 1990 7142
39. A.A. Ivanov, I. Fricks, T. Kendall Harden, and K.A. Jacobson Molecular dynamics simulation of the P2Y14 receptor. Ligand docking and identification of a putative binding site of the distal hexose moiety Bioorg. Med. Chem. Lett. 17 2007 761 766
40. J. Saam, E. Tajkhorshid, S. Hayashi, and K. Schulten Molecular dynamics investigation of primary photoinduced events in the activation of rhodopsin Biophys. J. 83 2002 3097 3112
41. S. Costanzi, B.V. Joshi, S. Maddileti, L. Mamedova, M.J. Gonzalez-Moa, V.E. Marquez, T.K. Harden, and K.A. Jacobson Human P2Y(6) receptor: molecular modeling leads to the rational design of a novel agonist based on a unique conformational preference J. Med. Chem. 48 2005 8108 8111
42. M.E. Zwaagstra, H. Timmerman, M. Tamura, T. Tohma, Y. Wada, K. Onogi, and M.Q. Zhang Synthesis and structure-activity relationships of carboxylated chalcones: a novel series of CysLT1 (LTD4) receptor antagonists J. Med. Chem. 40 1997 1075 1089
43. V. Capra, S. Ravasi, M.R. Accomazzo, M. Parenti, and G.E. Rovati CysLT1 signal transduction in differentiated U937 cells involves the activation of the small GTP-binding protein Ras Biochem. Pharmacol. 67 2004 1569 1577