Synthesis and labeling of α-(2,9)-trisialic acid with cyanine dyes for imaging of glycan-binding receptors on living cells

Chem Commun (Camb). 2015 May 21;51(41):8606-9. doi: 10.1039/c5cc01907a.

Abstract

A sugar epitope, α-(2,9)-trisialic acid, was synthesized and labeled by cyanine dyes through Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The cyanine tagged oligosialic acid can be utilized as an efficient fluorescent probe to image the glycan-binding receptors on PC-12 cells. The distribution of Sia-binding immunoglobulin-like lectins (Siglecs) for α-(2,9)-trisialic acid was visualized by Cy3/Cy5 or FRET channel fluorescence imaging.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbocyanines / chemical synthesis*
  • Carbocyanines / chemistry*
  • Cell Survival
  • Fluorescent Dyes / chemistry*
  • Molecular Structure
  • PC12 Cells
  • Polysaccharides / metabolism*
  • Rats
  • Receptors, Cell Surface / analysis*
  • Receptors, Cell Surface / metabolism*
  • Sialic Acids / chemical synthesis*
  • Sialic Acids / chemistry*
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry*

Substances

  • Carbocyanines
  • Fluorescent Dyes
  • Polysaccharides
  • Receptors, Cell Surface
  • Sialic Acids
  • Trisaccharides