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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
Valles Miret, M.
Fernández-Carneado, Jimena
Ponsati, Berta
Macías Hernández, María J.
Riera i Escalé, Antoni
Keywords: Pèptids
Hormones peptídiques
Compostos aromàtics
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:
It is part of: Scientific Reports, 2016, vol. 6, p. 27285
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ISSN: 2045-2322
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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