A graftable LDV peptidomimetic: design, synthesis and application to a blood filtration membrane

Bioorg Med Chem Lett. 2008 Feb 1;18(3):1084-90. doi: 10.1016/j.bmcl.2007.12.006. Epub 2007 Dec 8.

Abstract

A graftable LDV (Leu-Asp-Val) peptidomimetic molecule (B-c) has been prepared from 3-(5-amino-2-hydroxy)phenyl-propionic acid, as alpha(4)beta(1) (VLA-4) integrin ligand. For that purpose, the mechanism of 3-(4-azidophenyl)propionic acid rearrangement has been revisited. Activation of Durapore DVPP-hydrophilic membrane, by surface wet chemistry using triazine trifluoride, followed by covalent coupling of B-c produced a modified filter (0.8% of derivatisation from XPS analysis) with improved capacity of leukocyte retention.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Drug Design
  • Humans
  • Integrin alpha4beta1 / blood
  • Integrin alpha4beta1 / drug effects*
  • Leukocytes / drug effects*
  • Membranes, Artificial
  • Molecular Mimicry
  • Molecular Structure
  • Oligopeptides / blood
  • Oligopeptides / chemical synthesis*
  • Phenylpropionates / chemistry*
  • Polyvinyls / chemistry
  • Polyvinyls / metabolism
  • Structure-Activity Relationship

Substances

  • 3-(4-azidophenyl)propionic acid
  • 3-(5-amino-2-hydroxy)phenyl-propionic acid
  • Integrin alpha4beta1
  • Membranes, Artificial
  • Oligopeptides
  • Phenylpropionates
  • Polyvinyls
  • leucyl-aspartyl-valine
  • polyvinylidene fluoride