Docking and 3D QSAR study of thiourea analogs as potent inhibitors of influenza virus neuraminidase

Journal of Molecular Modeling

Volumn 16, Issue 12, 2010, Pages 1809-1818

  Sun, Jiaying ^a   Cai, Shaoxi ^a   Mei, Hu ^a   Li, Jian ^a   Yan, Ning ^a   Wang, Yuanqiang ^b  

^a CHONGQING UNIVERSITY   (China)

^b CHONGQING UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Docking; HoVAIF; Neuraminidase inhibitors; QSAR; Thiourea analogs

Indexed keywords

ANTIVIRUS AGENT; SIALIDASE INHIBITOR; THIOUREA DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; CORRELATION COEFFICIENT; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; ELECTRIC POTENTIAL; ENZYME INHIBITION; HYDROGEN BOND; HYDROPHOBICITY; IC 50; INFLUENZA VIRUS; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

ANTIVIRAL AGENTS; BINDING SITES; COMPUTER SIMULATION; DRUG DESIGN; ENZYME INHIBITORS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEURAMINIDASE; ORTHOMYXOVIRIDAE; PROTEIN BINDING; PROTEIN CONFORMATION; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; STATIC ELECTRICITY; THIOUREA;

ORTHOMYXOVIRIDAE; RUMEX;

EID: 79951736533     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-010-0685-9     Document Type: Article

References (35)

1. McKimm-Breschkin JL (2000) Resistance of influenza viruses to neuraminidase (Pubitemid 30621392)
2. Verma RP, Hansch C (2006) A QSAR study on influenza neuraminidase inhibitors. Bioorg Med Chem 14:982-996 (Pubitemid 43059790)
3. Stephenson I, Clark TW, Pareek M (2008) Antiviral treatment and prevention of seasonal influenza: a comparative review of recommendations in the European Union. J Clin Virol 42:244-248
4. Kim CU, Lew W, Williams MA, Wu H, Zhang LJ, Chen XW, Escarpe PA, Mendel DB, Graeme Laver W, Stevens RC (1998) Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors. J Med Chem 41:2451-2460 (Pubitemid 28321896)
5. Brouillette WJ, Atigadda VR, Luo M, Air GM, Babu YS, Bantia S (1999) Design of benzoic acid inhibitors of influenza neuraminidase containing a cyclic substitutuion for the N-acetyl grouping. Bioorg Med Chem Lett 9:1901-1906 (Pubitemid 29336370)
6. Wang GT, Chen YW, Wang S, Gentles R, Sowin T, Kati W, Muchmore S, Giranda V, Stewart K, Sham H, Kempf D, Laver WG (2001) Design, synthesis, and structural analysis of influenza neuraminidase inhibitors containing pyrrolidine cores. J Med Chem 44:1192-1201 (Pubitemid 32861754)
7. Krueger AC, Xu YB, Kati WM, Kempf DJ, Maring CJ, McDaniel KF, Molla A, Montgomery D, Kohlbrenner WE (2008) Synthesis of potent pyrrolidine influenza neuraminidase inhibitors. Bioorg Med Chem Lett 18:1692-1695 (Pubitemid 351318239)
8. Sun CW, Zhang XD, Huang H, Zhou P (2006) Synthesis and evaluation of a new series of substituted acyl(thio)urea and thiadiazolo [2, 3-a] pyrimidine derivatives as potent inhibitors of influenza virus neuraminidase. Bioorg Med Chem 14:8574-8581 (Pubitemid 44667533)
9. Yi X, Guo Z, Chu FM (2003) Study on molecular mechanism and 3D-QSAR of influenza neuraminidase inhibitors. Bioorg Med Chem 11:1465-1474 (Pubitemid 36293540)
10. Lü WJ, Chen YL, Ma WP, Zhang XY, Luan F, Liu MC, Chen XG, Hu ZD (2008) QSAR study of neuraminidase inhibitors based on heuristic method and radial basis function network. Eur J Med Chem 43:569-576
11. Nair PC, Sobhia ME (2008) Quantitative structure activity relationship studies on thiourea analogues as influenza virus neuraminidase inhibitors. Eur J Med Chem 43:293-299 (Pubitemid 351215598)
12. Liu SS, Cai SC, Cao CZ, Li ZS (2000) Molecular electronegative distance vector (MEDV) related to 15 properties of alkanes. J Chem Inf Comput Sci 40:1337-1348
13. Taylor NR, Cleasby A, Singh O, Skarzynski T, Wonacott AJ, Smith PW, Sollis SL, Howes PD, Cherry PC, Bethell R, Colman P, Varghese J (1998) Dihydropyrancarboxamides related to zanamivir: a new series of inhibitors of influenza virus sialidases. 2. Crystallographic and molecular modeling study of complexes of 4-amino-4H-pyran-6-carboxamides and sialidase from influenza virus types A and B. J Med Chem 41:798-807
14. Jain AN (2003) Surflex: fully automatic flexible molecular docking using a molecular similarity-based search engine. J Med Chem 46:499-511 (Pubitemid 36182752)
15. Ruppert J, Welch W, Jain AN (1997) Automatic identification and representation of protein binding sites for molecular docking. Protein Sci 6:524-533 (Pubitemid 27120049)
16. Muthas D, Sabnis YA, Lundborg M, Karlén A (2008) Is it possible to increase hit rates in structure-based virtual screening by pharmacophore filtering? An investigation of the advantages and pitfalls of post-filtering. J Mol Graph Model 26:1237-1251
17. Clark RD (2008) A ligand's-eye view of protein binding. J Comput Aided Mol Des 22:507-521
18. Clark RD, Strizhev A, Leonard JM, Blake JF, Matthew JB (2002) Consensus scoring for ligand/protein interactions. J Mol Graph Model 20:281-295 (Pubitemid 34017546)
19. Jones G, Willet P, Glen RC, Leach AR, Taylor R (1997) Development and validation of a genetic algorithm for flexible docking. J Mol Biol 267:727-748 (Pubitemid 27170693)
20. Muegge I, Martin YC (1999) A general and fast scoring function for protein-ligand interactions: a simplified potential approach. J Med Chem 42:791-804 (Pubitemid 29136170)
21. Kuntz ID, Blaney JM, Oatley SJ, Langridge R, Ferrin TE (1982) A geometric approach to macromolecule-ligand interactions. J Mol Biol 161:269-288
22. Eldridge MD, Murray CW, Auton TR, Paolini GV, Mee RP (1997) Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J Comput Aided Mol Des 11:425-445 (Pubitemid 127505895)
23. Levitt M (1983) Protein folding by restrained energy minimization and molecular dynamics. J Mol Biol 170:723-764
24. Levitt M, Perutz MF (1988) Aromatic rings act as hydrogen bond acceptors. J Mol Biol 201:751-754
25. Kellogg GE, Burnett JC, Abraham DJ (2001) Very empirical treatment of solvation and entropy; a force field derived from Log Po/w. J Comput Aided Mol Des 15:381-393 (Pubitemid 32366727)
26. Kellogg GE, Semus SF, Abraham DJ (1991) HINT-a new method of empirical hydrophobic field calculation for CoMFA. J Comput Aided Mol Des 5:545-552
27. Hahn M (1995) Receptor surface models. 1. Definition and construction. Med Chem 38:2080-2090
28. Abraham DJ, Kellogg GE, Holt JM, Ackers GK (1997) Hydropathic analysis of the non-covalent interactions between molecular subunits of structurally characterized hemoglobins. Mol Biol 272:613-632 (Pubitemid 27429846)
29. Gunnarsson GT, Umesh RD (2004) Hydropathic interaction analyses of small organic activators binding to antithrombin. Bioorg Med Chem 12:633-640 (Pubitemid 38102233)
30. Pei J, Wang Q, Zhou J, Lai L (2004) Estimating protein-ligand binding free energy; atomic solvation parameters for partition coefficient and solvation free energy calculation. Proteins 57:651-664 (Pubitemid 39626987)
31. Kellogg GE, Joshi GS, Abraham DJ (1992) New tools for modeling and understanding hydrophobicity and hydrophobic interactions. Med Chem Res 1:444-453
32. Kellogg GE, Abraham DJ (1992) Complementary hydrophobicity map predictions of drug structure from a known receptor/receptor structure from known drugs. J Mol Graph 10:212-217
33. Hasel W, Hendrikson TF, Still WC (1988) A rapid approximation to the solvent accessible surface areas of atoms. Tetrahedron Comput Methodol 1:103-116
34. Clark M, Crame RD (1993) The probability of chance correlation using partial least squares (PLS). Quant Struct Act Relat 2:137-145 (Pubitemid 23203836)
35. Yao SW, Lopes VHC, Fernández F, García-Mera X, Morales M, Rodríguez-Borges JE, Cordeiro MNDS (2003) Synthesis and QSAR study of the anticancer activity of some novel indane carbocyclic nucleosides. Bioorg Med Chem 11:4999-5006 (Pubitemid 37352987)