Recruitment of SH-containing peptides to lipid and biological membranes through the use of a palmitic acid functionalized with a maleimide group

Angew Chem Int Ed Engl. 2015 Jan 2;54(1):323-6. doi: 10.1002/anie.201408089. Epub 2014 Nov 21.

Abstract

This study presents a novel and easily applicable approach to recruit sulfhydryl-containing biomolecules to membranes by using a palmitic acid which is functionalized with a maleimide group. Notably, this strategy can also be employed with preformed (biological) membranes. The applicability of the assay is demonstrated by characterizing the binding of a Rhodamine-labeled peptide to lipid and cellular membranes using methods of fluorescence spectroscopy, lifetime measurement, and microscopy. Our approach offers new possibilities for preparing biologically active liposomes and manipulating living cells.

Keywords: liposomes; maleimide; membranes; palmitic acid; palmitoylation; peptides.

MeSH terms

  • Cell Membrane / metabolism*
  • Liposomes / chemistry
  • Liposomes / metabolism*
  • Macrophages / cytology
  • Macrophages / metabolism
  • Maleimides / chemistry
  • Maleimides / metabolism*
  • Microscopy, Confocal
  • Palmitic Acid / chemistry
  • Palmitic Acid / metabolism*
  • Peptides / chemistry
  • Peptides / metabolism*
  • Spectrometry, Fluorescence
  • Sulfhydryl Compounds / analysis
  • Sulfhydryl Compounds / metabolism*

Substances

  • Liposomes
  • Maleimides
  • Peptides
  • Sulfhydryl Compounds
  • maleimide
  • Palmitic Acid