Cyclic DGR-peptidomimetic containing a bicyclic reverse turn inducer as a selective alpha(v)beta (5) integrin ligand

Amino Acids. 2010 Jan;38(1):329-37. doi: 10.1007/s00726-009-0255-6. Epub 2009 Mar 7.

Abstract

3-Aza-6,8-dioxabicyclo[3.2.1]octane-based amino acids as reverse turn inducers have been introduced into cyclic peptidomimetics containing the RGD or DGR retro-sequence, in order to achieve a stereochemical scanning of the binding capability of the resulting molecules towards alpha(v)beta(3) and alpha(v)beta(5) integrins, resulting in retro-inverso DGR peptides as micromolar ligands. A comparative analysis between the conformational preferences of 4 and of its isomer 3, having the opposite RGD sequence, was reported with respect to the binding activity, giving insight into the factors affecting the preferential binding of 4 to the alpha(v)beta(5) integrin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Female
  • Humans
  • Kinetics
  • Ligands
  • Peptides, Cyclic / agonists
  • Peptides, Cyclic / chemical synthesis
  • Peptides, Cyclic / chemistry*
  • Placenta / chemistry
  • Placenta / metabolism
  • Pregnancy
  • Protein Binding
  • Receptors, Vitronectin / chemistry*
  • Receptors, Vitronectin / metabolism

Substances

  • Ligands
  • Peptides, Cyclic
  • Receptors, Vitronectin
  • cyclic arginine-glycine-aspartic acid peptide
  • integrin alphaVbeta5