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Title: | Peptide aromatic interactions modulated by fluorinated residues: Synthesis, structure and biological activity of Somatostatin analogs containing 3-(3',5'difluorophenyl)-alanine |
Author: | Martín-Gago, Pablo Rol Rúa, Álvaro Todorovski, Toni Aragón Altarriba, Eric Martin-Malpartida, Pau Verdaguer i Espaulella, Xavier Vallès Miret, Mariona Fernández-Carneado, Jimena Ponsati, Berta Macías Hernández, María J. Riera i Escalé, Antoni |
Keywords: | Pèptids Somatostatina Hormones peptídiques Compostos aromàtics Peptides Somatostatin Peptide hormones Aromatic compounds |
Issue Date: | 7-Jun-2016 |
Publisher: | Nature Publishing Group |
Abstract: | Somatostatin is a 14-residue peptide hormone that regulates the endocrine system by binding to five G-protein-coupled receptors (SSTR1-5). We have designed six new Somatostatin analogs with L-3-(3',5'-difluorophenyl)-alanine (Dfp) as a substitute of Phe and studied the effect of an electron-poor arom. ring in the network of arom. interactions present in Somatostatin. Replacement of each of the Phe residues (positions 6, 7 and 11) by Dfp and use of a D-Trp8 yielded peptides whose main conformations could be characterized in aq. soln. by NMR. Receptor binding studies revealed that the analog with Dfp at position 7 displayed a remarkable affinity to SSTR2 and SSTR3. Analogs with Dfp at positions 6 or 11 displayed a π-π interaction with the Phe present at 11 or 6, resp. Interestingly, these analogs, particularly [D-Trp8,L-Dfp11]-SRIF, showed high selectivity towards SSTR2, with a higher value than that of Octreotide and a similar one to that of native Somatostatin. |
Note: | Reproducció del document publicat a: http://dx.doi.org/10.1038/srep27285 |
It is part of: | Scientific Reports, 2016, vol. 6, p. 27285 |
URI: | http://hdl.handle.net/2445/101682 |
Related resource: | http://dx.doi.org/10.1038/srep27285 |
ISSN: | 2045-2322 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) Publicacions de projectes de recerca finançats per la UE |
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