The discovery of novel vascular endothelial growth factor receptor tyrosine kinases inhibitors: Pharmacophore modeling, virtual screening and docking studies

Chemical Biology and Drug Design

Volumn 69, Issue 3, 2007, Pages 204-211

  Yu, Hui ^a   Wang, Zhanli ^b   Zhang, Liangren ^c   Zhang, Jufeng ^a   Huang, Qian ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

^b NeoTrident Technology Ltd   (China)

^c PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Catalyst; Docking; HipHop; Kinase insert domain containing receptor kinase; Pharmacophore; Virtual screening

Indexed keywords

PROTEIN TYROSINE KINASE INHIBITOR; VASCULOTROPIN RECEPTOR;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG BINDING; DRUG SCREENING; ENDOTHELIUM CELL; ENZYME ACTIVE SITE; HUMAN; HUMAN CELL; HYDROGEN BOND; HYPOTHESIS; MOLECULAR DOCKING; PHARMACOPHORE; PRIORITY JOURNAL; UMBILICAL VEIN;

CATALYSIS; CELLS, CULTURED; DRUG EVALUATION, PRECLINICAL; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; PHOSPHORYLATION; PROTEIN KINASE INHIBITORS; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, VASCULAR ENDOTHELIAL GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34247273996     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2007.00488.x     Document Type: Article

References (29)

1. Millauer B., Wizigmann-Voos S., Schnurch H., Martinez R., Moller N.P., Risau W., Ullrich A. (1993) High affinity VEGF binding and developmental expression suggest Flk-1 as a major regulator of vasculogenesis and angiogenesis. Cell;72:835-846.
2. Quinn T.P., Peters K.G., De Vries C., Ferrara N., Williams L.T. (1993) Fetal liver kinase 1 is a receptor for vascular endothelial growth factor and is selectively expressed in vascular endothelium. Proc Natl Acad Sci USA;90:7533-7537.
3. Peters K., Werner S., Liao X., Wert S., Whitsett J., Williams L. (1994) Targeted expression of a dominant negative FGF receptor blocks branching morphogenesis and epithelial differentiation of the mouse lung. EMBO J;13:3296-3301.
4. Plate K.H., Breier G., Weich H.A., Risau W. (1992) Vascular endothelial growth factor is a potential tumour angiogenesis factor in human gliomas in vivo. Nature;359:845-848.
5. Plate K.H., Breier G., Weich H.A., Mennel H.D., Risau W. (1994) Vascular endothelial growth factor and glioma angiogenesis: coordinate induction of VEGF receptors, distribution of VEGF protein and possible in vivo regulatory mechanisms. Int J Cancer;59:520-529.
6. Yoshiji H., Gomez D.E., Shibuya M., Thorgeirsson U.P. (1996) Expression of vascular endothelial growth factor, its receptor, and other angiogenic factors in human breast cancer. Cancer Res;56:2013-2016.
7. O'Brien T., Cranston D., Fuggle S., Bicknell R., Harris A.L. (1995) Different angiogenic pathways characterize superficial and invasive bladder cancer. Cancer Res;55:510-513.
8. Shifren J.L., Tseng J.F., Zaloudek C.J., Ryan I.P., Meng Y.G., Ferrara N., Jaffe R.B., Taylor R.N. (1996) Ovarian steroid regulation of vascular endothelial growth factor in the human endometrium: implications for angiogenesis during the menstrual cycle and in the pathogenesis of endometriosis. J Clin Endocrinol Metab;81:3112-3118.
9. Strawn L.M., McMahon G., App H., Schreck R., Kuchler W.R., Longhi M.P., Hui T.H. et al. (1996) Flk-1 as a target for tumor growth inhibition. Cancer Res;56:3540-3545.
10. Prewett M., Huber J., Li Y., Santiago A., O'Connor W., King K., Overholser J., Hooper A., Pytowski B., Witte L., Bohlen P., Hicklin D.J. (1999) Antivascular endothelial growth factor receptor (fetal liver kinase 1) monoclonal antibody inhibits tumor angiogenesis and growth of several mouse and human tumors. Cancer Res;59:5209-5218.
11. Boyer S.J. (2002) Small molecule inhibitors of KDR (VEGFR-2) kinase: an overview of structure activity relationships. Curr Top Med Chem;2:973-1000.
12. Weng D.E., Usman N. (2001) Angiozyme: a novel angiogenesis inhibitor. Curr Oncol Rep;3:141-146.
13. Wood J.M., Bold G., Buchdunger E., Cozens R., Ferrari S., Frei J., Hofmann F. et al. (2000) PTK787/ZK222584, a novel and potent inhibitor of vascular endothelial growth factor receptor tyrosine kinases, impairs vascular endothelial growth factor-induced responses and tumor growth after oral administration. Cancer Res;60:2178-2189.
14. Wedge S.R., Ogilvie D.J., Dukes M., Kendrew J., Chester R., Jackson J.A., Boffey S.J. et al. (2002) ZD6474 inhibits vascular endothelial growth factor signaling, angiogenesis, and tumor growth following oral administration. Cancer Res;62:4645-4655.
15. Fraley M.E., Hoffman W.F., Arrington K.L., Hungate R.W., Hartman G.D., McFall R.C., Coll K.E., Rickert K., Thomas K.A., McGaughey G.B. (2004) Property-based design of KDR kinase inhibitors. Curr Med Chem;11:709-719.
16. Bajorath J. (2002) Integration of virtual and high-throughput screening. Nat Rev Drug Discov;1:882-894.
17. Hahn M. (1997) Three-dimensional shape-based searching of conformationally flexible compounds. J Chem Inf Comput Sci;37:80-86.
18. Putta S., Lemmen C., Beroza P., Greene J. (2002) A novel shape-feature based approach to virtual library screening. J Chem Inf Comput Sci;42:1230-1240.
19. Dai Y., Guo Y., Frey R.R., Ji Z., Curtin M.L., Ahmed A.A., Albert D.H. et al. (2005) Thienopyrimidine ureas as novel and potent multitargeted receptor tyrosine kinase inhibitors. J Med Chem;48:6066-6083.
20. Borzilleri R.M., Zheng X., Qian L., Ellis C., Cai Z.W., Wautlet B.S., Mortillo S. et al. (2005) Design, synthesis, and evaluation of orally active 4-(2,4-difluoro-5- (methoxycarbamoyl) phenylamino) pyrrolo [2,1-f] [1,2,4] triazines as dual vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1 inhibitors. J Med Chem;48:3991-4008.
21. Sun L., Tran N., Tang F., App H., Hirth P., McMahon G., Tang C. (1998) Synthesis and biological evaluations of 3-substituted indolin-2-ones: a novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases. J Med Chem;41:2588-2603.
22. Hennequin L.F., Thomas A.P., Johnstone C., Stokes E.S.E., Plé P.A., Lohmann J.M., Ogilvie D.J., Dukes M., Wedge S.R., Curwen J.O., Kendrew J., Lambert-van der Brempt C. (1999) Design and structure-activity relationship of a new class of potent VEGF receptor tyrosine kinase inhibitors. J Med Chem;42:5369-5389.
23. Sun L., Tran N., Liang C., Hubbard S., Tang F., Lipson K., Schreck R., Zhou Y., Waltz K., McMahon G., Tang C. (2000) Identification of substituted 3-[(4,5,6,7- tetrahydro-1H-indol- 2-yl) methylene]-1,3-dihydroindol-2-ones as growth factor receptor inhibitors for VEGF-R2 (Flk-1/KDR), FGF-R1 and PDGF-R tyrosine kinases. J Med Chem;43:2655-2663.
24. Bold G., Altmann K.-H., Frei J., Lang M., Manley P.W., Traxler P., Wietfeld B. et al. (2000) New anilinophthalazines as potent and orally well absorbed inhibitors of the VEGF receptor tyrosine kinases useful as antagonists of tumor-driven angiogenesis. J Med Chem;43:2310-2323.
25. Miyazaki Y., Matsunaga S., Tang J., Maeda Y., Nakano M., Philippe R.J., Shibahara M., Liu W., Sato H., Wang L., Nolte R.T. (2005) Novel 4-amino-furo [2,3-d] pyrimidines as Tie-2 and VEGFR2 dual inhibitors. Bioorg Med Chem Lett;15:2203-2207.
26. Barnum D., Greene J., Smellie A., Sprague P. (1996) Identification of common functional configurations among molecules. J Chem Inf Comput Sci;36:563-571.
27. Brooks B.R., Brucolleri R.E., Olafson B.D., States D.J., Swaminathan S., Karplus M. (1983) CHARMM: a program for macromolecular energy minimization, and dynamic calculations. J Comput Chem;4:187-217.
28. Smellie A., Teig S.L., Towbin P. (1995) Poling: promoting conformational variation. J Comput Chem;16:171-187.
29. Walters W.P., Murcko M.A. (2002) Prediction of 'drug-likeness'. Adv Drug Deliv Rev;54:255-271.