Investigation of the Best Conditions to Obtain c(RGDfK) Peptide on Solid Phase(508 views) Saviano M, Del Gatto A, De Simone M, De Paola I, Saviano M, Zaccaro L
Int J Pept Res Ther (ISSN: 1573-3149, 0929-5666), 2011 Mar; 17(1): 39-45.
Keywords: Optimisation, Pharmaceuticals, Reaction, Synthesis, Cyclo(arginylglycylaspartylphenylalanyllysine), Cyclopeptide, Unclassified Drug, Article, Chemical Reaction, Dimerization, Drug Screening, Drug Synthesis, Peptide Synthesis, Process Optimization, Protein Modification, Solid Phase Synthesis, Cyclo (arginylglycylaspartylphenylalanyllysine),
Affiliations: *** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, Naples 80134, Italy
Dipartimento Delle Scienze Biologiche, Università Degli Studi di Napoli Federico II, Via Mezzocannone 16, Naples 80134, Italy
Istituto di Cristallografia-CNR, Via Giovanni Amendola 122/O, Bari 70126, Italy
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Brooks, P. C., Montgomery, A. M., Rosenfeld, M., Reisfeld, R. A., Hu, T., Klier, G., Cheresh, D. A., Integrin alpha v beta 3 antagonists promote tumor regression by inducing apoptosis of angiogenic blood vessels (1994) Cell, 79, pp. 1157-1164. , 7528107 10. 1016/0092-8674 (94) 90007-8 1: CAS: 528: DyaK2MXivVWqu7o%3D
Brooks, P. C., Clark, R. A., Cheresh, D. A., Requirement of vascular integrin alphavbeta3 for angiogenesis (1994) Science, 264, pp. 569-571. , 7512751 10. 1126/science. 7512751 1: CAS: 528: DyaK2cXjt1Sis7w%3D
Dechantsreiter, M. A., Planker, E., Matha, B., Lohof, E., Holzemann, G., Jonczyk, A., Goodman, S. L., Kessler, H., N-methylated cyclic RGD peptides as highly active and selective (v) 3 integrin antagonists (1999) Journal of Medicinal Chemistry, 42 (16), pp. 3033-3040. , DOI 10. 1021/jm970832g
Eliceiri, B. P., Cheresh, D. A., The role of v integrins during angiogenesis: Insights into potential mechanisms of action and clinical development (1999) Journal of Clinical Investigation, 103 (9), pp. 1227-1230
Eskens, F. A. L. M., Dumez, H., Hoekstra, R., Perschl, A., Brindley, C., Bottcher, S., Wynendaele, W., Van Oosterom, A. T., Phase I and pharmacokinetic study of continuous twice weekly intravenous administration of Cilengitide (EMD 121974), a novel inhibitor of the integrins v 3 and v 5 in patients with advanced solid tumours (2003) European Journal of Cancer, 39 (7), pp. 917-926. , DOI 10. 1016/S0959-8049 (03) 00057-1
Lambert, J. N., Mitchell, J. P., Roberts, K. D., The synthesis of cyclic peptides (2001) J Chem Soc Perkin Trans, 1, pp. 471-484. , 10. 1039/b001942i
MacDonald, T. J., Stewart, C. F., Kocak, M., Goldman, S., Ellenbogen, R. G., Phillips, P., Lafond, D., Kun, L. E., Phase I clinical trial of cilengitide in children with refractory brain tumors: Pediatric brain tumor consortium study PBTC-012 (2008) Journal of Clinical Oncology, 26 (6), pp. 919-924. , http: //jco. ascopubs. org/cgi/reprint/26/6/919, DOI 10. 1200/JCO. 2007. 14. 1812
McCusker, C. F., Kocienski, P. J., Boyle F. Thomas, Schatzlein, A. G., Solid-phase synthesis of c (RGDfK) derivatives: On-resin cyclisation and lysine functionalisation (2002) Bioorganic and Medicinal Chemistry Letters, 12 (4), pp. 547-549. , DOI 10. 1016/S0960-894X (01) 00799-5, PII S0960894X01007995
Nabors, L. B., Mikkelsen, T., Rosenfeld, S. S., Hochberg, F., Akella, N. S., Fisher, J. D., Cloud, G. A., Grossman, S. A., Phase I and correlative biology study of cilengitide in patients with recurrent malignant glioma (2007) Journal of Clinical Oncology, 25 (13), pp. 1651-1657. , DOI 10. 1200/JCO. 2006. 06. 6514
Investigation of the Best Conditions to Obtain c(RGDfK) Peptide on Solid Phase
The cyclic pentapeptide c(RGDfK) is a high affinity ligand of alphaVbeta3 integrin. It was an analog of Cilengitide (EMD 121974) developed to be employed as tracer for cancer diagnosis and therapy by functionalisation of its Lys side-chain. Solution-phase and solid-phase synthetic approaches were previously reported. In the attempt to improve solid-phase synthesis of the cyclopeptide circumventing cyclodimerisation reactions, a systematic study of the synthetic conditions was performed, evaluating and optimising parameters directly involved in the ring closure step. The three-dimensional orthogonal solid-phase strategy developed in this study yields the desired c(RGDfK) peptide with no cyclodimerisation by-products. The protocols described allow the modification of the peptide directly on the solid support in order to obtain novel derivatives for biomedical applications.
Investigation of the Best Conditions to Obtain c(RGDfK) Peptide on Solid Phase
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