Issue 9, 2015

Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH)

Abstract

Novel GnRH I and II analogues were designed and synthesized by Solid Phase Peptide Synthesis (SPPS), since GnRH has antiproliferative properties, but poor metabolic stability. To rationalize synthetic difficulties, molecular dynamics simulations were performed, showing the conformational behavior of three derivatives. Among the two series of peptidomimetics (Ie, f and IIe, f were GnRH I and GnRH II analogues, respectively), several compounds (Id–f and IIc–e) showed significant binding affinity. In particular, derivative Ie has an increased metabolic stability with respect to the physiological ligand (Iet1/2 = 3.96 h versus GnRH I t1/2 = 2.63 h).

Graphical abstract: Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH)

Supplementary files

Article information

Article type
Concise Article
Submitted
17 Jun 2015
Accepted
27 Jul 2015
First published
28 Jul 2015

Med. Chem. Commun., 2015,6, 1656-1665

Author version available

Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH)

A. Gelain, L. Rizzi, L. Legnani, A. Pacini, K. Spyridaki, V. Karageorgos, G. Liapakis and S. Villa, Med. Chem. Commun., 2015, 6, 1656 DOI: 10.1039/C5MD00259A

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