Robust fluorescent detection of protein fatty-acylation with chemical reporters

J Am Chem Soc. 2009 Apr 8;131(13):4967-75. doi: 10.1021/ja810122f.

Abstract

Fatty-acylation of proteins in eukaryotes is associated with many fundamental cellular processes but has been challenging to study due to limited tools for rapid and robust detection of protein fatty-acylation in cells. The development of azido-fatty acids enabled the nonradioactive detection of fatty-acylated proteins in mammalian cells using the Staudinger ligation and biotinylated phosphine reagents. However, the visualization of protein fatty-acylation with streptavidin blotting is highly variable and not ideal for robust detection of fatty-acylated proteins. Here we report the development of alkynyl-fatty acid chemical reporters and improved bioorthogonal labeling conditions using the Cu(I)-catalyzed Huisgen [3 + 2] cycloaddition that enables specific and sensitive fluorescence detection of fatty-acylated proteins in mammalian cells. These improvements allow the rapid and robust biochemical analysis of fatty-acylated proteins expressed at endogenous levels in mammalian cells by in-gel fluorescence scanning. In addition, alkynyl-fatty acid chemical reporters enable the visualization of fatty-acylated proteins in cells by fluorescence microscopy and flow cytometry. The ability to rapidly visualize protein fatty-acylation in cells using fluorescence detection methods therefore provides new opportunities to interrogate the functions and regulatory mechanisms of fatty-acylated proteins in physiology and disease.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Catalysis
  • Copper / chemistry
  • Cytological Techniques / methods*
  • Electrophoresis, Polyacrylamide Gel / methods
  • Fatty Acids / analysis*
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Humans
  • Jurkat Cells
  • Microscopy, Fluorescence / methods
  • Proteins / chemistry*

Substances

  • Fatty Acids
  • Fluorescent Dyes
  • Proteins
  • Copper