Issue 12, 2012
From the journal:

MedChemComm

Synthesis and binding affinities for sst receptors of cyclic peptoid SRIF-mimetics†

Cécile Caumes,ab   Thomas Hjelmgaard,ab   Olivier Roy,ab   Morgane Reynaud,c   Denis Servent,c   Claude Taillefumier*ab  and  Sophie Faure*ab  

* Corresponding authors

a Clermont Universités, Université Blaise Pascal, Institut de Chimie de Clermont-Ferrand (ICCF), BP 10448, 63000 Clermont-Ferrand, France

b CNRS, UMR 6296, Institut de chimie de Clermont-Ferrand, 63177 Aubière Cedex, France
E-mail: Sophie.Faure@univ-bpclermont.fr
Fax: +33 (0)4 73 40 77 17
Tel: +33 (0)4 73 40 52 25

c CEA, iBiTecS, Service d'Ingénierie Moléculaire des Protéines (SIMOPRO), 91191 Gif sur Yvette, France

Abstract

Mimicking the tetradecapeptide somatostatin through the design of novel non-peptide small molecules is needed for developing analogues with selective or universal affinity for human somatostatin receptors (hsst1–5) and improved pharmacological properties. We report the synthesis and evaluation of the binding potential of the first all-peptoid SRIF (somatotropin release-inhibiting factor) analogues. Cyclic β and mixed α/β tetra- or pentapeptoids were efficiently obtained by macrocyclisation of the corresponding linear peptoids. In vitro competition binding experiments using [125I]-somatostatin were performed on this first generation of peptoids mimicking the SRIF pharmacophore (Phe7-(D)Trp8-Lys9-Thr10). The selectivity profiles of cyclic compounds 1 to 4 were similar with higher affinity for the sst3, sst5 and sst4 receptors and lower potency on sst1 and sst2 subtypes.

Graphical abstract: Synthesis and binding affinities for sst receptors of cyclic peptoid SRIF-mimetics

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Article information

DOI
https://doi.org/10.1039/C2MD20265D
Article type
Concise Article
Submitted
06 Sep 2012
Accepted
09 Oct 2012
First published
09 Oct 2012

Med. Chem. Commun., 2012,3, 1531-1535

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Synthesis and binding affinities for sst receptors of cyclic peptoid SRIF-mimetics

C. Caumes, T. Hjelmgaard, O. Roy, M. Reynaud, D. Servent, C. Taillefumier and S. Faure, Med. Chem. Commun., 2012, 3, 1531 DOI: 10.1039/C2MD20265D

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