Pharmacophore-based 3D-QSAR as a predictive method for the QSAR analysis on a series of potent and selective inhibitors for three kinases of RTK family

Molecular Simulation

Volumn 36, Issue 9, 2010, Pages 693-707

  Jiang, Qinglin ^a   Liao, Hongli ^a   Yang, Qian ^a   Zan, Wang ^a   Zang, Zhihe ^a  

^a CHENGDU MEDICAL COLLEGE   (China)

Author keywords

3D QSAR; cKit; Flt1; KDR; pharmacophore

Indexed keywords

3D-QSAR; CKIT; FLT1; KDR; PHARMACOPHORES;

ENZYME INHIBITION; THREE DIMENSIONAL;

PHARMACODYNAMICS;

EID: 77955874630     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927021003752788     Document Type: Article

References (26)

1. P. Carmeliet and R.K. Jain, Angiogenesis in cancer and other diseases, Nature 407 (2000), pp. 249-257.
2. J. Folkman, Clinical applications of research on angiogenesis, N. Engl. J. Med. 333 (1995), pp. 1757-1763.
3. J. Folkman, Angiogenesis in cancer, vascular, rheumatoid and other disease, Nat. Med. 1 (1995), pp. 27-30.
4. B.R. Zetter, Angiogenesis and tumor metastasis, Annu. Rev. Med. 49 (1998), pp. 407-424.
5. J.T. Kuethe, A. Wong, C.X. Qu, J. Smitrovich, I.W. Davies, and D.L. Hughes, Synthesis of 5-substituted-1H-indol-2-yl-1Hquinolin-2-ones: A novel class of KDR kinase inhibitors, J. Org. Chem. 70 (2005), pp. 2555-2567.
6. K.A. Thomas, Vascular endothelial growth factor, a potent and selective angiogenic agent, J. Biol. Chem. 271 (1996), pp. 603-606.
7. B.I. Terman, M. Dougher-Vermazen, M.E. Carrion, D. Dimitrov, D.C. Armellino, D. Gospodarowicz, and P. Bohlen, Identification of the KDR tyrosine kinase as a receptor for vascular endothelial cell growth factor, Biochem. Biophys. Res. Commun. 187 (1992), pp. 1579-1586.
8. C. De Vries, J.A. Escobedo, H. Ueno, K. Houck, N. Ferrara, and L.T. Williams, The fms-like tyrosine kinase, a receptor for vascular endothelial growth factor, Science 255 (1992), pp. 989-991.
9. G.D. Yancopoulos, S. Davis, N.W. Gale, J.S. Rudge, S.J. Wiegand, and J. Holash, Vascular-specific growth factors and blood vessel formation, Nature 407 (2000), pp. 242-248.
10. M.T. Bilodeau, M.E. Fraley, and G.D. Hartman, Kinase insert domain-containing receptor kinase inhibitors as anti-angiogenic agents, Expert Opin. Investig. Drugs 11 (2002), pp. 737-745.
11. M. Shibuya and L. Claesson-Welsh, Signal transduction by VEGF receptors in regulation of angiogenesis and lymphangiogenesis, Exp. Cell Res. 312 (2006), pp. 549-560.
12. M.M. Dikov, J.E. Ohm, N. Ray, E.E. Tchekneva, J. Burlison, D. Moghanaki, S. Nadaf, and D.P. Carbone, Differential roles of vascular endothelial growth factor receptors 1 and 2 in dendritic cell differentiation, J. Immunol. 174 (2005), pp. 215-222.
13. C.D. Mol, D.R. Dougan, T.R. Schneider, R.J. Skene, M.L. Kraus, D.N. Scheibe, G.P. Snell, H. Zou, B.C. Sang, and K.P. Wilson, Structural basis for the autoinhibition and STI-571 inhibition of c-Kit tyrosine kinase, J. Biol. Chem. 279 (2004), pp. 31655-31663.
14. N. Ferrara and T. Davis-Smyth, The biology of vascular endothelial growth factor, Endocr. Rev. 18 (1997), pp. 4-25.
15. P. Borgstroem, K.J. Hillan, P. Sriramarao, and N. Ferrara, Complete inhibition of angiogenesis and growth of microtumors by antivascular endothelial growth factor neutralizing antibody: Novel concepts of angiostatic therapy from intravital video microscopy, Cancer Res. 56 (1996), pp. 4032-4039.
16. A.P. Adamis, D.T. Shima, M.J. Tolentino, E.S. Gragoudas, N. Ferrara, J. Folkman, P.A. D'Amore, and J.W. Miller, Inhibition of vascular endothelial growth factor prevents retinal ischemiaassociated iris neovascularization in a nonhuman primate, Arch. Ophthalmol. 114 (1996), pp. 66-71. (Pubitemid 26026196)
17. P. Prathipati, G. Pandey, and A.K. Saxena, CoMFA and docking studies on glycogen phosphorylase a inhibitors as antidiabetic agents, J. Chem. Inf. Model. 45 (2005), pp. 136-145.
18. S.J. Cho, M.L. Garsia, J. Bier, and A. Tropsha, Structure-based alignment and comparative molecular field analysis of acetylcholinesterase inhibitors, J. Med. Chem. 39 (1996), pp. 5064-5071.
19. I. Akritopoulou-Zanze, D.H. Albert, P.F. Bousquet, G.A. Cunha, C.M. Harris, M. Moskey, J. Dinges, K.D. Stewart, and T.J. Sowin, Synthesis and biological evaluation of 5-substituted 1,4-dihydroindeno[ 1,2-c]pyrazoles as multitargeted receptor tyrosine kinase inhibitors, Bioorg. Med. Chem. Lett. 17 (2007), pp. 3136-3140.
20. J. Dinges, K.L. Ashworth, I. Akritopolou-Zanze, L.D. Arnold, S.A. Baumeister, P.F. Bousquet, G.A. Cunha, S.K. Davidsen, S.W. Djuric, V.J. Gracias, M.R. Michaelides, P. Rafferty, T.J. Sowin, K.D. Stewart, Z. Xia, and H.Q. Zhang, 1,4-Dihydroindeno[1,2-c]pyrazoles as novel multitargeted receptor tyrosine kinase inhibitors, Bioorg. Med. Chem. Lett. 16 (2006), pp. 4266-4271.
21. R.C. Wade, Molecular interaction fields, in 3D QSAR in Drug Design, H. Kubinyi, ed., ESCOM, Leiden, 1993, pp. 486-505.
22. S. Wold, E. Johansson, and M. Cocchi, PLS-partial least squares projections to latent structures, in 3D QSAR in Drug Design, Theory Methods and Applications, H. Kubinyi, ed., ESCOM, Leiden, 1993, pp. 523-550.
23. G. Klebe, U. Abraham, and T. Mietzner, Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity, J. Med. Chem. 37 (1994), pp. 4130-4146.
24. G. Klebe and U. Abraham, Comparative molecular similarity index analysis (CoMSIA) to study hydrogen-bonding properties and to score combinatorial libraries, J. Comput.-Aided Mol. Des. 13 (1999), pp. 1-10.
25. M. Bohm, J. Sturzebecher, and G. Klebe, Three-dimensional quantitative structure-activity relationship analyses using comparative molecular field analysis and comparative molecular similarity indices analysis to elucidate selectivity differences of inhibitors binding to trypsin, thrombin, and factor Xa, J. Med. Chem. 42 (1999), pp. 458-477.
26. S.S. Chaudhaery, K.R. Kuldeep, and A.K. Saxena, Consensus superiority of the pharmacophore-based alignment, over maximum common substructure (MCS): 3D-QSAR studies on carbamates as acetylcholinesterase inhibitors, J. Chem. Inf. Model. 49 (2009), pp. 1590-1601.