Development of Activity-Based Probes for Imaging Human α-l-Fucosidases in Cells

J Org Chem. 2015 Aug 21;80(16):8458-63. doi: 10.1021/acs.joc.5b01204. Epub 2015 Aug 10.

Abstract

We have established a concise synthetic route relying on a key base-promoted epimerization step to synthesize two series of activity-based probes carrying a BODIPY fluorophore for α-l-fucosidase. The resulting probes were evaluated for labeling performance. The one utilizing an o-fluoromethylphenol derivative as the latent trapping unit was successfully applied for the first time to visualize and locate lysosomal α-l-fucosidase activity in human cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemistry*
  • Cell Membrane / chemistry*
  • Cell Membrane / enzymology
  • Fluorescence
  • Humans
  • Kinetics
  • Phenols / chemistry*
  • alpha-L-Fucosidase / chemistry*

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Phenols
  • alpha-L-Fucosidase