Keywords: Alanine, Cyclopeptide, Immunoglobulin, Ligand, Macrocyclic Compound, Mitogen Activated Protein Kinase 1, Receptor Blocking Agent, Tubulin, Unclassified Drug, Vascular Endothelial Growth Factor Receptor Antagonist, Vasculotropin, Vasculotropin Receptor, Amino Acid Substitution, Article, Controlled Study, Derivatization, Drug Binding Site, Drug Receptor Binding, Endothelium Cell, Human, Human Cell, Molecular Probe, Protein Domain, Proton Nuclear Magnetic Resonance, Structure Analysis, Amino Acid Sequence, Animals, Chemiluminescent Measurements, Heterocyclic Compounds, Magnetic Resonance Spectroscopy, Models, Molecular Imaging, Phosphorylation, Protein Binding, Protein Conformation, Signal Transduction, Structure-Activity Relationship, Substrate Specificity,
Affiliations: *** IBB - CNR ***
Université Paris Descartes, UFR Biomédicale, Laboratoire de PharmacochimieMoléculaire et Cellulaire, 45 rue des Saints Péres, 75006 Paris, France
Dipartimento di Scienze Ambientali, Seconda Universitá di Napoli via Vivaldi 43, 81100 Caserta, Italy
Istituto di Biostrutture e Bioimmagini, CNR, via Mezzocannone, 16, 80134 Napoli, Italy
Université de Perpignan Via Domitia, Laboratoire de Chimie des Biomolécules, 52 avenue Paul Alduy, 66860 Perpignan, France
Universit Paris Descartes, UFR Biom dicale, Laboratoire de PharmacochimieMol culaire et Cellulaire, 45 rue des Saints P res, 75006 Paris, France
Universit de Perpignan Via Domitia, Laboratoire de Chimie des Biomol cules, 52 avenue Paul Alduy, 66860 Perpignan, France
References: Ferrara, N., Kerbel, R.S., Angiogenesis as a therapeutic target (2005) Nature, 438, pp. 967-97
Carmeliet, P., Jain, R.K., Angiogenesis in cancer and other diseases (2000) Nature, 407, pp. 249-257
Takahashi, H., Shibuya, M., The vascular endothelial growth factor (VEGF)/VEGF receptor system and its role under physiological and pathological conditions (2005) Clin. Sci. (London), 109, pp. 227-241
Carmeliet, P., Angiogenesis in life, disease and medicine (2005) Nature, 438, pp. 932-936
Folkman, J., Tumor angiogenesis: Therapeutic implications (1971) N. Engl. J. Med., 285, pp. 1182-1186
Jain, R.K., Normalization of tumor vasculature: An emerging concept in antiangiogenic therapy (2005) Science, 307, pp. 58-62
Shinkaruk, S., Bayle, M., Lain, G., Deleris, G., Vascular endothelial cell growth factor (VEGF), an emerging target for cancer chemotherapy (2003) Curr. Med. Chem. Anticancer Agents, 3, pp. 95-117
Ellis, L.M., Hicklin, D.J., VEGF-targeted therapy: Mechanisms of anti-tumour activity (2008) Nat. Rev. Cancer, 8, pp. 579-591
Ferrara, N., Gerber, H.P., Lecouter, J., The biology of VEGF and its receptors (2003) Nat. Med., 9, pp. 669-676
Roskoski Jr., R., Vascular endothelial growth factor (VEGF) signaling in tumor progression (2007) Crit. Rev. Oncol. Hematol.
De Paepe, B., Anti-angiogenic agents and cancer: Current insights and future perspectives (2009) Recent Pat. Anticancer Drug Discovery, 4, pp. 180-185
Ferrara, N., Hillan, K.J., Novotny, W., Bevacizumab (Avastin), a humanized anti-VEGF monoclonal antibody for cancer therapy (2005) Biochem. Biophys. Res. Commun., 333, pp. 328-335
Ferrara, N., Mass, R.D., Campa, C., Kim, R., Targeting VEGF-A to treat cancer and age-related macular degeneration (2007) Annu. Rev. Med., 58, pp. 491-504
Gerber, D., Targeted therapies: A new generation of cancer treatments (2008) Am. Acad. Family Physicians, 77, pp. 311-319
Wilhelm, S.M., Adnane, L., Newell, P., Villanueva, A., Llovet, J.M., Lynch, M., Preclinical overview of sorafenib, a multikinase inhibitor that targets both Raf and VEGF and PDGF receptor tyrosine kinase signaling (2008) Mol. Cancer Ther., 7, pp. 3129-3140
Faivre, S., Demetri, G., Sargent, W., Raymond, E., Molecular basis for sunitinib efficacy and future clinical development (2007) Nat. Rev. Drug Discovery, 6, pp. 734-745
Posey, J.A., Ng, T.C., Yang, B., Khazaeli, M.B., Carpenter, M.D., Fox, F., Needle, M., Lobuglio, A.F., A phase i study of anti-kinase insert domain-containing receptor antibody, IMC-1C11, in patients with liver metastases from colorectal carcinoma (2003) Clin. Cancer Res., 9, pp. 1323-1332
Delano, W.L., Unraveling hot spots in binding interfaces: Progress and challenges (2002) Curr. Opin. Struct. Biol., 12, pp. 14-20
Veslovsky, A.V., Archakov, A.I., Inhibitors of protein-protein interaction as potential drugs (2007) Curr. Comput.-Aided Drug Des., 3, pp. 51-58
D'Andrea, L.D., Del Gatto, A., De Rosa, L., Romanelli, A., Pedone, C., Peptides targeting angiogenesis related growth factor receptors (2009) Curr. Pharm. Des., 15, pp. 2414-2429
Goncalves, V., Gautier, B., Garbay, C., Vidal, M., Inguimbert, N., Structure-based design of a bicyclic peptide antagonist of the vascular endothelial growth factor receptors (2007) J. Pept. Sci.
Wiesmann, C., Fuh, G., Christinger, H.W., Eigenbrot, C., Wells, J.A., De Vos, A.M., Crystal structure at 1.7 A resolution of VEGF in complex with domain 2 of the Flt-1 receptor (1997) Cell, 91, pp. 695-704
Christinger, H.W., Fuh, G., De Vos, A.M., Wiesmann, C., The crystal structure of placental growth factor in complex with domain 2 of vascular endothelial growth factor receptor-1 (2004) J. Biol. Chem., 279, pp. 10382-10388
Keyt, B.A., Nguyen, H.V., Berleau, L.T., Duarte, C.M., Park, J., Chen, H., Ferrara, N., Identification of vascular endothelial growth factor determinants for binding KDR and FLT-1 receptors. Generation of receptor-selective VEGF variants by site-directed mutagenesis (1996) J. Biol. Chem., 271, pp. 5638-5646
Muller, Y.A., Li, B., Christinger, H.W., Wells, J.A., Cunningham, B.C., De Vos, A.M., Vascular endothelial growth factor: Crystal structure and functional mapping of the kinase domain receptor binding site (1997) Proc. Natl. Acad. Sci. U.S.A., 94, pp. 7192-7197
Li, B., Fuh, G., Meng, G., Xin, X., Gerritsen, M.E., Cunningham, B., De Vos, A.M., Receptor-selective variants of human vascular endothelial growth factor. Generation and characterization (2000) J. Biol. Chem., 275, pp. 29823-29828
Errico, M., Riccioni, T., Iyer, S., Pisano, C., Acharya, K.R., Persico, M.G., De Falco, S., Identification of placenta growth factor determinants for binding and activation of Flt-1 receptor (2004) J. Biol. Chem., 279, pp. 43929-43939
Goncalves, V.G.B., Lenoir, C., Garbay, C., Vidal, M., Inguimbert, N., Peptides as antagonists of the VEGF receptors (2006) PharmaChem, pp. 15-19
Gautier, B., Goncalves, V., Huguenot, F., Garbay, C., Vidal, M., Inguimbert, N., unpublished resultsOlsson, A.K., Dimberg, A., Kreuger, J., Claesson-Welsh, L., VEGF receptor signalling-in control of vascular function (2006) Nat. Rev. Mol. Cell Biol., 7, pp. 359-371
Chang, C.D., Meienhofer, J., Solid-phase peptide-synthesis using mild base cleavage of nalpha-fluorenylmethyloxycarbonylamino acids, exemplified by a synthesis of dihydrosomatostatin (1978) Int. J. Pept. Protein Res., 11, pp. 246-249
Kates, S.A., Sole, N.A., Johnson, C.R., Hudson, D., Barany, G., Albericio, F.A., A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides (1993) Tetrahedron. Lett., 34, pp. 1549-1552
Johnson, T., Liley, M.J., Cheeseright, T.J., Begum, F., Problems in the synthesis of cyclic peptides through use of the Dmab protecting group (2000) J. Chem. Soc., Perkin Trans., 43, pp. 2811-2820
Starzec, A., Ladam, P., Vassy, R., Badache, S., Bouchemal, N., Navaza, A., Du Penhoat, C.H., Perret, G.Y., Structure-function analysis of the antiangiogenic ATWLPPR peptide inhibiting VEGF(165) binding to neuropilin-1 and molecular dynamics simulations of the ATWLPPR/neuropilin-1 complex (2007) Peptides, 28, pp. 2397-2402
Yongye, A.B., Li, Y., Giulianotti, M.A., Yu, Y., Houghten, R.A., Martinez-Mayorga, K., Modeling of peptides containing D-amino acids: Implications on cyclization (2009) J. Comput.-Aided Mol. Des., 23, pp. 677-689
Chamorro, C., Kruijtzer, J.A., Farsaraki, M., Balzarini, J., Liskamp, R.M., A general approach for the non-stop solid phase synthesis of TAC-scaffolded loops towards protein mimics containing discontinuous epitopes (2009) Chem. Commun. (Camb.), pp. 821-823
Barleon, B., Totzke, F., Herzog, C., Blanke, S., Kremmer, E., Siemeister, G., Marme, D., Martiny-Baron, G., Mapping of the sites for ligand binding and receptor dimerization at the extracellular domain of the vascular endothelial growth factor receptor FLT-1 (1997) J. Biol. Chem., 272, pp. 10382-10388
Lacal, P.M., Morea, V., Ruffini, F., Orecchia, A., Dorio, A.S., Failla, C.M., Soro, S., D'Atri, S., Inhibition of endothelial cell migration and angiogenesis by a vascular endothelial growth factor receptor-1 derived peptide (2008) Eur. J. Cancer, 44, pp. 1914-1921
Starovasnik, M.A., Christinger, H.W., Wiesmann, C., Champe, M.A., De Vos, A.M., Skelton, N.J., Solution structure of the VEGF-binding domain of Flt-1: Comparison of its free and bound states (1999) J. Mol. Biol., 293, pp. 531-544
Leppanen, V.M., Prota, A.E., Jeltsch, M., Anisimov, A., Kalkkinen, N., Strandin, T., Lankinen, H., Alitalo, K., Structural determinants of growth factor binding and specificity by VEGF receptor 2 (2010) Proc. Natl. Acad. Sci. U.S.A., 107, pp. 2425-2430
Millauer, B., Wizigmann-Voos, S., Schnurch, H., Martinez, R., Moller, N.P., Risau, W., Ullrich, A., High affinity VEGF binding and developmental expression suggest Flk-1 as a major regulator of vasculogenesis and angiogenesis (1993) Cell, 72, pp. 835-846
Bernatchez, P.N., Soker, S., Sirois, M.G., Vascular endothelial growth factor effect on endothelial cell proliferation, migration, and platelet-activating factor synthesis is Flk-1-dependent (1999) J. Biol. Chem., 274, pp. 31047-31054
Waltenberger, J., Claesson-Welsh, L., Siegbahn, A., Shibuya, M., Heldin, C.H., Different signal transduction properties of KDR and Flt1, two receptors for vascular endothelial growth factor (1994) J. Biol. Chem., 269, pp. 26988-26995
Gille, H., Kowalski, J., Yu, L., Chen, H., Pisabarro, M.T., Davis-Smyth, T., Ferrara, N., A repressor sequence in the juxtamembrane domain of Flt-1 (VEGFR-1) constitutively inhibits vascular endothelial growth factor-dependent phosphatidylinositol 3′-kinase activation and endothelial cell migration (2000) Embo J., 19, pp. 4064-4073
Fuh, G., Wu, P., Liang, W.C., Ultsch, M., Lee, C.V., Moffat, B., Wiesmann, C., Structure-function studies of two synthetic anti-vascular endothelial growth factor Fabs and comparison with the Avastin Fab (2006) J. Biol. Chem., 281, pp. 6625-6631
Vidal, M., Liu, W.Q., Lenoir, C., Salzmann, J., Gresh, N., Garbay, C., Design of peptoid analogue dimers and measure of their affinity for Grb2 SH3 domains (2004) Biochemistry, 43, pp. 7336-7344
Hajduk, P.J., Meadows, R.P., Fesik, S.W., NMR-based screening in drug discovery (1999) Q. Rev. Biophys., 32, pp. 211-240
Keller, R., (2004) The Computer Aided Resonance Assignment Tutorial, , CANTINA Verlag: Goldau
Garrett, D.S., Seok, Y.J., Peterkofsky, A., Clore, G.M., Gronenborn, A.M., Identification by NMR of the binding surface for the histidine-containing phosphocarrier protein HPr on the N-terminal domain of enzyme i of the Escherichia coli phosphotransferase system (1997) Biochemistry, 36, pp. 4393-4398
Koradi, R., Billeter, M., Wuthrich, K., MOLMOL: A program for display and analysis of macromolecular structures (1996) J. Mol. Graph., 14 (51-55), pp. 29-32
Jain, R. K., Normalization of tumor vasculature: An emerging concept in antiangiogenic therapy (2005) Science, 307, pp. 58-62
Ellis, L. M., Hicklin, D. J., VEGF-targeted therapy: Mechanisms of anti-tumour activity (2008) Nat. Rev. Cancer, 8, pp. 579-591
Lau, S. C., Rosa, D. D., Jayson, G., Technology evaluation: VEGF Trap (cancer), Regeneron/sanofi-aventis (2005) Curr. Opin. Mol. Ther., 7, pp. 493-501
Wilhelm, S. M., Adnane, L., Newell, P., Villanueva, A., Llovet, J. M., Lynch, M., Preclinical overview of sorafenib, a multikinase inhibitor that targets both Raf and VEGF and PDGF receptor tyrosine kinase signaling (2008) Mol. Cancer Ther., 7, pp. 3129-3140
Posey, J. A., Ng, T. C., Yang, B., Khazaeli, M. B., Carpenter, M. D., Fox, F., Needle, M., Lobuglio, A. F., A phase i study of anti-kinase insert domain-containing receptor antibody, IMC-1C11, in patients with liver metastases from colorectal carcinoma (2003) Clin. Cancer Res., 9, pp. 1323-1332
Delano, W. L., Unraveling hot spots in binding interfaces: Progress and challenges (2002) Curr. Opin. Struct. Biol., 12, pp. 14-20
Veslovsky, A. V., Archakov, A. I., Inhibitors of protein-protein interaction as potential drugs (2007) Curr. Comput. -Aided Drug Des., 3, pp. 51-58
D'Andrea, L. D., Del Gatto, A., De Rosa, L., Romanelli, A., Pedone, C., Peptides targeting angiogenesis related growth factor receptors (2009) Curr. Pharm. Des., 15, pp. 2414-2429
Keyt, B. A., Nguyen, H. V., Berleau, L. T., Duarte, C. M., Park, J., Chen, H., Ferrara, N., Identification of vascular endothelial growth factor determinants for binding KDR and FLT-1 receptors. Generation of receptor-selective VEGF variants by site-directed mutagenesis (1996) J. Biol. Chem., 271, pp. 5638-5646
Muller, Y. A., Li, B., Christinger, H. W., Wells, J. A., Cunningham, B. C., De Vos, A. M., Vascular endothelial growth factor: Crystal structure and functional mapping of the kinase domain receptor binding site (1997) Proc. Natl. Acad. Sci. U. S. A., 94, pp. 7192-7197
Goncalves, V. G. B., Lenoir, C., Garbay, C., Vidal, M., Inguimbert, N., Peptides as antagonists of the VEGF receptors (2006) PharmaChem, pp. 15-19
Chang, C. D., Meienhofer, J., Solid-phase peptide-synthesis using mild base cleavage of nalpha-fluorenylmethyloxycarbonylamino acids, exemplified by a synthesis of dihydrosomatostatin (1978) Int. J. Pept. Protein Res., 11, pp. 246-249
Kates, S. A., Sole, N. A., Johnson, C. R., Hudson, D., Barany, G., Albericio, F. A., A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides (1993) Tetrahedron. Lett., 34, pp. 1549-1552
Yongye, A. B., Li, Y., Giulianotti, M. A., Yu, Y., Houghten, R. A., Martinez-Mayorga, K., Modeling of peptides containing D-amino acids: Implications on cyclization (2009) J. Comput. -Aided Mol. Des., 23, pp. 677-689
Lacal, P. M., Morea, V., Ruffini, F., Orecchia, A., Dorio, A. S., Failla, C. M., Soro, S., D'Atri, S., Inhibition of endothelial cell migration and angiogenesis by a vascular endothelial growth factor receptor-1 derived peptide (2008) Eur. J. Cancer, 44, pp. 1914-1921
Starovasnik, M. A., Christinger, H. W., Wiesmann, C., Champe, M. A., De Vos, A. M., Skelton, N. J., Solution structure of the VEGF-binding domain of Flt-1: Comparison of its free and bound states (1999) J. Mol. Biol., 293, pp. 531-544
Leppanen, V. M., Prota, A. E., Jeltsch, M., Anisimov, A., Kalkkinen, N., Strandin, T., Lankinen, H., Alitalo, K., Structural determinants of growth factor binding and specificity by VEGF receptor 2 (2010) Proc. Natl. Acad. Sci. U. S. A., 107, pp. 2425-2430
Bernatchez, P. N., Soker, S., Sirois, M. G., Vascular endothelial growth factor effect on endothelial cell proliferation, migration, and platelet-activating factor synthesis is Flk-1-dependent (1999) J. Biol. Chem., 274, pp. 31047-31054
Vidal, M., Liu, W. Q., Lenoir, C., Salzmann, J., Gresh, N., Garbay, C., Design of peptoid analogue dimers and measure of their affinity for Grb2 SH3 domains (2004) Biochemistry, 43, pp. 7336-7344
Hajduk, P. J., Meadows, R. P., Fesik, S. W., NMR-based screening in drug discovery (1999) Q. Rev. Biophys., 32, pp. 211-240
Garrett, D. S., Seok, Y. J., Peterkofsky, A., Clore, G. M., Gronenborn, A. M., Identification by NMR of the binding surface for the histidine-containing phosphocarrier protein HPr on the N-terminal domain of enzyme i of the Escherichia coli phosphotransferase system (1997) Biochemistry, 36, pp. 4393-4398
Biochemical and Structural Analysis of the Binding Determinants of a Vascular Endothelial Growth Factor Receptor Peptidic Antagonist
Hesse B, Tagil K, Cuocolo A, Anagnostopoulos C, Bardies M, Bax J, Bengel F, Busemann Sokole E, Davies G, Dondi M, Edenbrandt L, Franken P, Kjaer A, Knuuti J, Lassmann M, Ljungberg M, Marcassa C, Marie PY, Mckiddie F, O'connor M, Prvuolovich E, Underwood R * 3. 0 T perfusion MR imaging(694 views) Rivista Di Neuroradiologia (ISSN: 1120-9976), 2004; 17(6): 807-812. Impact Factor:0.023 ViewExport to BibTeXExport to EndNote
Vitiello M, Finamore E, Falanga A, Raieta K, Cantisani M, Galdiero F, Pedone C, Galdiero M, Galdiero S * Fusion in Coq(479 views) Lecture Notes In Computer Science (ISSN: 0302-9743, 0302-974335404636319783540463634, 0302-974335402975459783540297543), 2001; 2178LNCS: 583-596. Impact Factor:0.415 ViewExport to BibTeXExport to EndNote