A backbone-cyclic, receptor 5-selective somatostatin analogue: synthesis, bioactivity, and nuclear magnetic resonance conformational analysis

Journal of Medicinal Chemistry
Chaim GilonH Kessler

Abstract

Cyclo(PheN2-Tyr-D-Trp-Lys-Val-PheC3)-Thr-NH2 (PTR 3046), a backbone-cyclic somatostatin analogue, was synthesized by solid-phase methodology. The binding characteristics of PTR 3046 to the different somatostatin receptors, expressed in CHO cells, indicate high selectivity to the SSTR5 receptor. PTR 3046 is highly stable against enzymatic degradation as determined in vitro by incubation with rat renal homogenate and human serum. The biological activity of PTR 3046 in vivo was determined in rats. PTR 3046 inhibits bombesin- and caerulein-induced amylase and lipase release from the pancreas without inhibiting growth hormone or glucagon release. The major conformation of PTR 3046 in CD3OH, as determined by NMR, is defined by a type II' beta-turn at D-Trp-Lys and a cis amide bond at Val-PheC3.

Citations

Sep 5, 2002·Biopolymers·M Altstein
May 21, 2013·European Journal of Nuclear Medicine and Molecular Imaging·Volker H SchartingerDaniel Putzer
Jul 21, 2006·Journal of Medicinal Chemistry·Christy Rani R GraceRoland Riek
May 1, 2001·The Journal of Peptide Research : Official Journal of the American Peptide Society·G GellermanM Kramer
Oct 19, 2001·The Journal of Peptide Research : Official Journal of the American Peptide Society·I ZeltserC Gilon
Nov 24, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·B MüllerS Reissmann
Jul 29, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·E FalbC Gilon
Jul 1, 2010·Expert Opinion on Drug Discovery·Oded OvadiaHorst Kessler
Dec 6, 2008·Trends in Endocrinology and Metabolism : TEM·Eric N ChurchillDaria Mochly-Rosen
Sep 15, 2005·Lung Cancer : Journal of the International Association for the Study of Lung Cancer·Genady KostenichArie Orenstein
Sep 4, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·Sebastian KuenzelSiegmund Reissmann
Aug 16, 2003·Endocrine Reviews·Jean Claude Reubi
Apr 15, 2000·The Journal of Biological Chemistry·A FriedlerC Gilon
Jun 23, 2015·Biopolymers·Ana I Fernández-LlamazaresFernando Albericio
May 15, 2002·The Journal of Peptide Research : Official Journal of the American Peptide Society·S GazalC Gilon
Sep 5, 2001·The Journal of Peptide Research : Official Journal of the American Peptide Society·A JaneckaT Janecki
Jan 16, 2002·Journal of Receptor and Signal Transduction Research·H Senderowitz, R Rosenfeld
Jan 24, 2008·Journal of Medicinal Chemistry·Debora D'AddonaMauro Ginanneschi
Dec 12, 2003·Journal of Medicinal Chemistry·Christy Rani R GraceRoland Riek

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