Literature DB >> 24900623

Stapled Vasoactive Intestinal Peptide (VIP) Derivatives Improve VPAC2 Agonism and Glucose-Dependent Insulin Secretion.

Fabrizio Giordanetto1, Jefferson D Revell2, Laurent Knerr1, Marie Hostettler3, Amalia Paunovic4, Claire Priest5, Annika Janefeldt1, Adrian Gill1.   

Abstract

Agonists of vasoactive intestinal peptide receptor 2 (VPAC2) stimulate glucose-dependent insulin secretion, making them attractive candidates for the treatment of hyperglycaemia and type-II diabetes. Vasoactive intestinal peptide (VIP) is an endogenous peptide hormone that potently agonizes VPAC2. However, VIP has a short serum half-life and poor pharmacokinetics in vivo and is susceptible to proteolytic degradation, making its development as a therapeutic agent challenging. Here, we investigated two peptide cyclization strategies, lactamisation and olefin-metathesis stapling, and their effects on VPAC2 agonism, peptide secondary structure, protease stability, and cell membrane permeability. VIP analogues showing significantly enhanced VPAC2 agonist potency, glucose-dependent insulin secretion activity, and increased helical content were discovered; however, neither cyclization strategy appeared to effect proteolytic stability or cell permeability of the resulting peptides.

Entities:  

Keywords:  VIP; VPAC; glucose tolerance; insulin secretion; lactamized peptide; peptide agonist; ring-closing metathesis; stapled peptide; vasoactive intestinal peptide

Year:  2013        PMID： 24900623      PMCID： PMC4027235          DOI： 10.1021/ml400257h

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  32 in total

1.  Development of selective agonists and antagonists for the human vasoactive intestinal polypeptide VPAC(2) receptor.

Authors:  D Moreno; P Gourlet; P De Neef; J Cnudde; M Waelbroeck; P Robberecht
Journal:  Peptides       Date:  2000-10       Impact factor: 3.750

2.  All-hydrocarbon stapled peptides as Synthetic Cell-Accessible Mini-Proteins.

Authors: 
Journal:  Drug Discov Today Technol       Date:  2012

3.  Stabilization of vasoactive intestinal peptide by lipids.

Authors:  G Gololobov; Y Noda; S Sherman; I Rubinstein; J Baranowska-Kortylewicz; S Paul
Journal:  J Pharmacol Exp Ther       Date:  1998-05       Impact factor: 4.030

4.  Stabilizing the pro-apoptotic BimBH3 helix (BimSAHB) does not necessarily enhance affinity or biological activity.

Authors:  Toru Okamoto; Kerry Zobel; Anna Fedorova; Clifford Quan; Hong Yang; Wayne J Fairbrother; David C S Huang; Brian J Smith; Kurt Deshayes; Peter E Czabotar
Journal:  ACS Chem Biol       Date:  2012-12-10       Impact factor: 5.100

5.  Isolation from porcine-intestinal wall of a vasoactive octacosapeptide related to secretin and to glucagon.

Authors:  S I Said; V Mutt
Journal:  Eur J Biochem       Date:  1972-07-13

6.  Vasoactive intestinal peptide (VIP) prevents neurotoxicity in neuronal cultures: relevance to neuroprotection in Parkinson's disease.

Authors:  D Offen; Y Sherki; E Melamed; M Fridkin; D E Brenneman; I Gozes
Journal:  Brain Res       Date:  2000-01-31       Impact factor: 3.252

7.  A potent and highly selective VPAC2 agonist enhances glucose-induced insulin release and glucose disposal: a potential therapy for type 2 diabetes.

Authors:  Manami Tsutsumi; Thomas H Claus; Yin Liang; Yaxin Li; Ling Yang; Jian Zhu; Fernando Dela Cruz; Xianbu Peng; Hongxing Chen; Stephanie L Yung; Sarah Hamren; James N Livingston; Clark Q Pan
Journal:  Diabetes       Date:  2002-05       Impact factor: 9.461

8.  Hydrocarbon double-stapling remedies the proteolytic instability of a lengthy peptide therapeutic.

Authors:  Gregory H Bird; Navid Madani; Alisa F Perry; Amy M Princiotto; Jeffrey G Supko; Xiaoying He; Evripidis Gavathiotis; Joseph G Sodroski; Loren D Walensky
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-21       Impact factor: 11.205

9.  Crystal structure of the incretin-bound extracellular domain of a G protein-coupled receptor.

Authors:  Christoph Parthier; Martin Kleinschmidt; Piotr Neumann; Rainer Rudolph; Susanne Manhart; Dagmar Schlenzig; Jörg Fanghänel; Jens-Ulrich Rahfeld; Hans-Ulrich Demuth; Milton T Stubbs
Journal:  Proc Natl Acad Sci U S A       Date:  2007-08-21       Impact factor: 11.205

10.  Functional expression and tissue distribution of a novel receptor for vasoactive intestinal polypeptide.

Authors:  T Ishihara; R Shigemoto; K Mori; K Takahashi; S Nagata
Journal:  Neuron       Date:  1992-04       Impact factor: 17.173
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  7 in total

Review 1.  Getting across the cell membrane: an overview for small molecules, peptides, and proteins.

Authors:  Nicole J Yang; Marlon J Hinner
Journal:  Methods Mol Biol       Date:  2015

2.  Dual-purpose linker for alpha helix stabilization and imaging agent conjugation to glucagon-like peptide-1 receptor ligands.

Authors:  Liang Zhang; Tejas Navaratna; Jianshan Liao; Greg M Thurber
Journal:  Bioconjug Chem       Date:  2015-01-28       Impact factor: 4.774

3.  A two-component 'double-click' approach to peptide stapling.

Authors:  Yu Heng Lau; Yuteng Wu; Peterson de Andrade; Warren R J D Galloway; David R Spring
Journal:  Nat Protoc       Date:  2015-03-12       Impact factor: 13.491

Review 4.  Structure-Based Design of Inhibitors of Protein-Protein Interactions: Mimicking Peptide Binding Epitopes.

Authors:  Marta Pelay-Gimeno; Adrian Glas; Oliver Koch; Tom N Grossmann
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-26       Impact factor: 15.336

5.  Maternal Fructose Exposure Programs Metabolic Syndrome-Associated Bladder Overactivity in Young Adult Offspring.

Authors:  Wei-Chia Lee; You-Lin Tain; Kay L H Wu; Steve Leu; Julie Y H Chan
Journal:  Sci Rep       Date:  2016-10-05       Impact factor: 4.379

6.  Structural and ITC Characterization of Peptide-Protein Binding: Thermodynamic Consequences of Cyclization Constraints, a Case Study on Vascular Endothelial Growth Factor Ligands.

Authors:  Jean-François Gaucher; Marie Reille-Seroussi; Sylvain Broussy
Journal:  Chemistry       Date:  2022-07-07       Impact factor: 5.020

7.  Influence of macrocyclization on allosteric, juxtamembrane-derived, stapled peptide inhibitors of the epidermal growth factor receptor (EGFR).

Authors:  Julie K-L Sinclair; Alanna Schepartz
Journal:  Org Lett       Date:  2014-09-10       Impact factor: 6.005
  7 in total

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