Tetraphenylethylene-based glycoconjugate as a fluorescence "turn-on" sensor for cholera toxin

Chem Asian J. 2011 Sep 5;6(9):2376-81. doi: 10.1002/asia.201100141. Epub 2011 Jul 11.


Tetraphenylethylene (TPE)-based glycoconjugates were easily synthesized by copper(I)-catalyzed "click reactions" between propargyl-attached TPE and azido-functionalized sugars. The TPE compound bearing lactosyl moieties (Lac-TPE) was found to be a fluorescence "turn-on" sensor for cholera toxin by virtue of aggregation-induced emission characteristics of the TPE motif owing to the specific interaction of lactose with the cholera toxin B subunit, whilst a cellobiose-functionalized TPE derivative did not show any response to the toxin. Therefore, Lac-TPE shows promising applications in the detection of cholera toxin, as well as in the investigation of carbohydrate-protein interaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biosensing Techniques / methods*
  • Cholera Toxin / analysis*
  • Crystallography, X-Ray
  • Ethylenes / chemistry*
  • Fluorescent Dyes / chemistry*
  • Glycoconjugates / chemistry*
  • Lactose / analogs & derivatives*
  • Lactose / chemical synthesis
  • Lactose / chemistry
  • Molecular Conformation
  • Spectrometry, Fluorescence / methods
  • Stilbenes / chemical synthesis
  • Stilbenes / chemistry*


  • Ethylenes
  • Fluorescent Dyes
  • Glycoconjugates
  • Stilbenes
  • Cholera Toxin
  • Lactose