Design and synthesis of a stable oxidized phospholipid mimic with specific binding recognition for macrophage scavenger receptors

J Med Chem. 2012 Sep 27;55(18):8178-82. doi: 10.1021/jm300685s. Epub 2012 Sep 11.

Abstract

Macrophage scavenger receptors appear to play a major role in the clearance of oxidized phospholipid (OxPL) products. Discrete peptide-phospholipid conjugates with the phosphatidylcholine headgroup have been shown to exhibit binding affinity for these receptors. We report the preparation of a water-soluble, stable peptide-phospholipid conjugate (9) that possesses the necessary physical properties to enable more detailed study of the role(s) of OxPL in metabolic disease.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Antibodies, Monoclonal / metabolism
  • Biomimetic Materials / chemical synthesis*
  • Biomimetic Materials / chemistry
  • Biomimetic Materials / metabolism*
  • CD36 Antigens / metabolism*
  • Chemistry Techniques, Synthetic
  • Drug Design*
  • Drug Stability
  • Humans
  • Mice
  • Oxidation-Reduction
  • Phospholipid Ethers / chemistry*
  • Phospholipid Ethers / metabolism
  • Protein Binding
  • Solubility
  • Substrate Specificity
  • Water / chemistry

Substances

  • 1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine
  • Antibodies, Monoclonal
  • CD36 Antigens
  • Phospholipid Ethers
  • Water