Anticancer molecules targeting fibroblast growth factor receptors

Trends in Pharmacological Sciences

Volumn 33, Issue 10, 2012, Pages 531-541

  Liang, Guang ^a   Liu, Zhiguo ^a   Wu, Jianzhang ^a   Cai, Yuepiao ^a   Li, Xiaokun ^a  

^a WENZHOU MEDICAL UNIVERSITY   (China)

Author keywords

anticancer agents; cancer chemical therapy; fibroblast growth factor receptor; receptor tyrosine kinase inhibitors; structure activity relationship

Indexed keywords

1 TERT BUTYL 3 [6 (3,5 DIMETHOXYPHENYL) 2 (4 DIETHYLAMINOBUTYLAMINO)PYRIDO[2,3 D]PYRIMIDIN 7 YL]UREA; 1,6 NAPHTHYRIDINE 2 ONE; 2 AMINO 7 (3 TERT BUTYLUREIDO) 6 (2,6 DICHLOROPHENYL)PYRIDO[2,3 D]PYRIMIDINE; 3 [4 METHYL 2 (2 OXO 3 INDOLINYLMETHYLIDENYL) 3 PYRROLYL]PROPIONIC ACID; 7 AZAINDOLE; ACENAPHTHO[1,2 B]PYRROLE; ANTINEOPLASTIC AGENT; ARQ 069; AZD 4547; BGJ 398; BRIVANIB; CISPLATIN; DOVITINIB; EXEMESTANE; FIBROBLAST GROWTH FACTOR RECEPTOR; FIIN 1; FP 1039; IMIDAZO[1,2 A] PYRIDINE; INDAZOLE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE; NINTEDANIB; ORANTINIB; OXINDOLE; PACLITAXEL; PD 166866; PYRIDO[2,3 D]PYRIMIDINE DERIVATIVE; PYRROLO[2,1 F] [1,2,4]TRIAZINE; QUINOLINE; SU 4984; TEPROTUMUMAB; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ADVANCED CANCER; ANTINEOPLASTIC ACTIVITY; BREAST CANCER; CANCER COMBINATION CHEMOTHERAPY; CLINICAL EFFECTIVENESS; CLINICAL RESEARCH; COLORECTAL CANCER; DRUG DETERMINATION; DRUG EFFECT; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; DRUG POTENTIATION; DRUG SAFETY; ENDOMETRIUM CANCER; ESOPHAGUS CANCER; EXTRACELLULAR MATRIX; HUMAN; IC 50; KIDNEY CARCINOMA; LIVER CELL CARCINOMA; LUNG CANCER; LUNG NON SMALL CELL CANCER; MALIGNANT NEOPLASTIC DISEASE; METASTASIS; MOLECULAR DOCKING; MOLECULARLY TARGETED THERAPY; MULTIPLE MYELOMA; NONHUMAN; OVARY CANCER; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN BINDING; REVIEW; STOMACH CANCER; STRUCTURE ACTIVITY RELATION; TRANSITIONAL CELL CARCINOMA; TREATMENT DURATION;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG DESIGN; HUMANS; LIGANDS; MOLECULAR DOCKING SIMULATION; PROTEIN KINASE INHIBITORS; RECEPTORS, FIBROBLAST GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84866736540     PISSN: 01656147     EISSN: 18733735     Source Type: Journal    
DOI: 10.1016/j.tips.2012.07.001     Document Type: Review

References (62)

1. E. Li Role of receptor tyrosine kinase transmembrane domains in cell signaling and human pathologies Biochemistry 45 2006 6241 6251 (Pubitemid 43787791)
2. A.M. Xu Receptor tyrosine kinase coactivation networks in cancer Cancer Res. 70 2010 3857 3860
3. J. Zhang Targeting cancer with small molecule kinase inhibitors Nat. Rev. Cancer 9 2009 28 39
4. Y.R. Hadari Critical role for the docking-protein FRS2 alpha in FGF receptor-mediated signal transduction pathways Proc. Natl. Acad. Sci. U.S.A. 98 2001 8578 8583 (Pubitemid 32678070)
5. N. Turner Fibroblast growth factor signalling: from development to cancer Nat. Rev. Cancer 10 2010 116 129
6. V.D. Acevedo Paths of FGFR-driven tumorigenesis Cell Cycle 8 2009 580 588
7. V.P. Eswarakumar Cellular signaling by fibroblast growth factor receptors Cytokine Growth Factor Rev. 16 2010 139 149 (Pubitemid 40616112)
8. H. Greulich Targeting mutant fibroblast growth factor receptors in cancer Trends Mol. Med. 17 2011 283 292
9. J. Wesche Fibroblast growth factors and their receptors in cancer Biochem. J. 437 2011 199 213
10. M. Mohammadi Structures of the tyrosine kinase domain of fibroblast growth factor receptor in complex with inhibitors Science 276 1997 955 960 (Pubitemid 27209095)
11. T. Ishibe Disruption of fibroblast growth factor signal pathway inhibits the growth of synovial sarcomas: potential application of signal inhibitors to molecular target therapy Clin. Cancer Res. 11 2005 2702 2712 (Pubitemid 40569472)
12. L. Sun Design, synthesis, and evaluations of substituted 3-[(3- or 4-carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF receptor tyrosine kinases J. Med. Chem. 42 1999 5120 5130 (Pubitemid 30020263)
13. L. Sun 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-Rβ tyrosine kinases J. Med. Chem. 43 2000 2655 2663 (Pubitemid 30463914)
14. P.W. Manley Advances in the structural biology, design and clinical development of VEGF-R kinase inhibitors for the treatment of angiogenesis Biochim. Biophys. Acta 1697 2004 17 27 (Pubitemid 38326758)
15. G.J. Roth Design, synthesis, and evaluation of indolinones as triple angiokinase inhibitors and the discovery of a highly specific 6-methoxycarbonyl-substituted indolinone (BIBF 1120) J. Med. Chem. 52 2009 4466 4480
16. J.M. Hamby Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors J. Med. Chem. 40 1997 2296 2303 (Pubitemid 27342564)
17. C.C. Chiang Discovery of pyrrole-indoline-2-ones as aurora kinase inhibitors with a different inhibition profile J. Med. Chem. 53 2010 5929 5941
18. G.W. Krystal Indolinone tyrosine kinase inhibitors block Kit activation and growth of small cell lung cancer cells Cancer Res. 61 2001 3660 3668 (Pubitemid 32694977)
19. N. Kammasud 5-Substituted pyrido[2,3-d]pyrimidine, an inhibitor against three receptor tyrosine kinases Bioorg. Med. Chem. Lett. 19 2009 745 750
20. A.M. Thompson Synthesis and structure-activity relationships of soluble 7-substituted 3-(3,5-dimethoxyphenyl)-1,6-naphthyridin-2-amines and related ureas as dual inhibitors of the fibroblast growth factor receptor-1 and vascular endothelial growth factor receptor-2 tyrosine kinases J. Med. Chem. 48 2005 4628 4653 (Pubitemid 40993423)
21. M. Mohammadi Crystal structure of an angiogenesis inhibitor bound to the FGF receptor tyrosine kinase domain EMBO J. 17 1998 5896 5904 (Pubitemid 28474784)
22. N.H. Nam Current targets for anticancer drug discovery Curr. Drug Targets 4 2003 159 179
23. S. Trumpp-Kallmeyer Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors J. Med. Chem. 41 1998 1752 1763 (Pubitemid 28248652)
24. D.A. Ibrahim Design, synthesis and biological study of novel pyrido[2,3-d]pyrimidine as anti-proliferative CDK2 inhibitors Eur. J. Med. Chem. 46 2011 5825 5832
25. S.R. Klutchko 2-Substituted aminopyrido[2,3-d]pyrimidin-7(8H)-ones. Structure-activity relationships against selected tyrosine kinases and in vitro and in vivo anticancer activity J. Med. Chem. 41 1998 3276 3292 (Pubitemid 28376533)
26. D.H. Boschelli Synthesis and tyrosine kinase inhibitory activity of a series of 2-amino-8H-pyrido[2,3-d]pyrimidines: identification of potent, selective platelet-derived growth factor receptor tyrosine kinase inhibitors J. Med. Chem. 41 1998 4365 4377 (Pubitemid 28498760)
27. A.J. Kraker Biochemical and cellular effects of c-Src kinase-selective pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors Biochem. Pharmacol. 60 2000 885 898
28. M. Barvian Pyrido[2,3-d]pyrimidin-7-one inhibitors of cyclin-dependent kinases J. Med. Chem. 43 2000 4606 4616
29. L.F. Hennequin Design and structure-activity relationship of a new class of potent VEGF receptor tyrosine kinase inhibitors J. Med. Chem. 42 1999 5369 5389 (Pubitemid 30036772)
30. K. Frazier Design and structure-activity relationship of heterocyclic analogs of 4-amino-3-benzimidazol-2-ylhydroquinolin-2-ones as inhibitors of receptor tyrosine kinases Bioorg. Med. Chem. Lett. 16 2006 2247 2251 (Pubitemid 43351088)
31. J. Hackett Development of keratinocyte growth factor receptor tyrosine kinase inhibitors for the treatment of cancer Anticancer Res. 27 2007 3801 3806
32. P.A. Renhowe Design, structure-activity relationships and in vivo characterization of 4-amino-3-benzimidazol-2-ylhydroquinolin-2-ones: a novel class of receptor tyrosine kinase inhibitors J. Med. Chem. 52 2008 278 292
33. T.E. Hutson Targeted therapies for the treatment of metastatic renal cell carcinoma: clinical evidence Oncologist 16 2011 14 22
34. N.E. Hynes Potential for targeting the fibroblast growth factor receptors in breast cancer Cancer Res. 70 2010 5199 5202
35. J. Tsai Discovery of a selective inhibitor of oncogenic B-Raf kinase with potent antimelanoma activity Proc. Natl. Acad. Sci. U.S.A. 105 2008 3041 3046 (Pubitemid 351723664)
36. H.R. Tsou Discovery and optimization of 2-(4-substituted-pyrrolo[2,3-b] pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR) Bioorg. Med. Chem. Lett. 20 2010 2321 2325
37. N.D. Adams Discovery of GSK1070916, a potent and selective inhibitor of Aurora B/C kinase J. Med. Chem. 53 2010 3973 4001
38. C.M. McBride Design and structure-activity relationship of 3-benzimidazol-2-yl-1H-indazoles as inhibitors of receptor tyrosine kinases Bioorg. Med. Chem. Lett. 16 2006 3595 3599 (Pubitemid 43777111)
39. E.E. Boros Synthesis and antiviral activity of 7-benzyl-4-hydroxy-1,5- naphthyridin-2(1H)-one HIV integrase inhibitors J. Med. Chem. 52 2009 2754 2761
40. A.M. Thompson 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase J. Med. Chem. 43 2000 4200 4211
41. A.M. Thompson Synthesis and structure-activity relationships of 7-substituted 3-(2, 6-dichlorophenyl)-1,6-naphthyridin-2(1H)-ones as selective inhibitors of pp60(c-src) J. Med. Chem. 43 2000 3134 3147 (Pubitemid 30626769)
42. R.M. Borzilleri 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 2005 3991 4008 (Pubitemid 40800608)
43. R.S. Bhide Discovery and preclinical studies of (R)-1-(4-(4-fluoro-2- methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)propan- 2-ol (BMS-540215), an in vivo active potent VEGFR-2 inhibitor J. Med. Chem. 49 2006 2143 2146
44. M. Squires Potent, selective inhibitors of fibroblast growth factor receptor define fibroblast growth factor dependence in preclinical cancer models Mol. Cancer Ther. 10 2011 1542 1552
45. G. Trapani Synthesis and binding affinity of 2-phenylimidazo[1,2-α] pyridine derivatives for both central and peripheral benzodiazepine receptors. A new series of high-affinity and selective ligands for the peripheral type J. Med. Chem. 40 1997 3109 3118 (Pubitemid 27391543)
46. Z. Chen Acenaphtho[1,2-b]pyrrole-based selective fibroblast growth factor receptors 1 (FGFR1) inhibitors: design, synthesis, and biological activity J. Med. Chem. 54 2011 3732 3745
47. H. Huynh Targeting receptor tyrosine kinase pathways in hepatocellular carcinoma Anticancer Agents Med. Chem. 11 2011 560 575
48. J. Bain The selectivity of protein kinase inhibitors: a further update Biochem. J. 408 2007 297 315
49. P. Bamborough Assessment of chemical coverage of kinome space and its implications for kinase drug discovery J. Med. Chem. 51 2008 7898 7914
50. V. Guagnano Discovery of 3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-{6-[4- (4-ethyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-methyl-urea (NVP-BGJ398), a potent and selective inhibitor of the fibroblast growth factor receptor family of receptor tyrosine kinase J. Med. Chem. 54 2011 7066 7083
51. R.A. Norman Protein-ligand crystal structures can guide the design of selective inhibitors of the FGFR tyrosine kinase J. Med. Chem. 55 2012 5003 5012
52. P.R. Gavine AZD4547: an orally bioavailable, potent, and selective inhibitor of the fibroblast growth factor receptor tyrosine kinase family Cancer Res. 72 2012 2045 2056
53. X.H. Ma In-silico approaches to multi-target drug discovery: computer aided multi-target drug design, multi-target virtual screening Pharm. Res. 27 2010 739 749
54. W. Zhou A structure-guided approach to creating covalent FGFR inhibitors Chem. Biol. 17 2010 285 295
55. S. Eathiraj A novel mode of protein kinase inhibition exploiting hydrophobic motifs of autoinhibited kinases: discovery of ATP-independent inhibitors of fibroblast growth factor receptor J. Biol. Chem. 286 2011 20677 20687
56. O. Gorbenko Generation of monoclonal antibody targeting fibroblast growth factor receptor 3 Hybridoma 28 2009 295 300
57. J. Qing Antibody-based targeting of FGFR3 in bladder carcinoma and t(4;14)-positive multiple myeloma in mice J. Clin. Invest. 119 2009 1216 1229
58. D.P. Bottaro A keratinocyte growth factor receptor-derived peptide antagonist identifies part of the ligand binding site J. Biol. Chem. 268 1993 9180 9183 (Pubitemid 23145956)
59. P. Wong Analysis of putative heparin-binding domains of fibroblast growth factor-1. Using site-directed mutagenesis and peptide analogues J. Biol. Chem. 270 1995 25805 25811
60. H. Fan Selection of peptide ligands binding to fibroblast growth factor receptor 1 IUBMB Life 54 2002 67 72 (Pubitemid 35278621)
61. X. Wu Isolation of a novel basic FGF-binding peptide with potent antiangiogenetic activity J. Cell. Mol. Med. 14 2010 351 356
62. C. Wang Mechanism of antitumor effect of a novel bFGF binding peptide on human colon cancer cells Cancer Sci. 101 2010 1212 1218