LDV peptidomimetics equipped with biotinylated spacer-arms: synthesis and biological evaluation on CCRF-CEM cell line

Bioorg Med Chem Lett. 2012 Jan 1;22(1):586-90. doi: 10.1016/j.bmcl.2011.10.078. Epub 2011 Oct 31.

Abstract

The tripeptide Leu-Asp-Val (LDV) is known to bind α(4)β(1) integrin in leukemia cells. Here we have synthesized a LDV peptidomimetic equipped with a biotin-conjugated spacer-arm. Compound 9 acts as an inhibitor of the α(4)β(1) integrin in an adhesion assay using fluorescently labeled, α(4)β(1) integrin-expressing leukemia CCRF-CEM cells. Furthermore, when bound to neutravidin-coated plates, compound 9 could capture CCRF-CEM cells. Such biotin-conjugated LDV peptidomimetic may thus represent a novel tool for biotechnological applications using avidin interaction for leukapheresis or leukemia cell targeting.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / pharmacology
  • Biotin / chemistry
  • Cell Adhesion
  • Cell Line
  • Cell Line, Tumor
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Gene Expression Regulation, Leukemic
  • Humans
  • Inhibitory Concentration 50
  • Integrin alpha4beta1 / metabolism
  • Kinetics
  • Leukemia / metabolism
  • Models, Chemical
  • Oligopeptides / chemistry*
  • Peptides / chemistry
  • Peptidomimetics / chemistry*

Substances

  • Antineoplastic Agents
  • Integrin alpha4beta1
  • Oligopeptides
  • Peptides
  • Peptidomimetics
  • leucyl-aspartyl-valine
  • Biotin