Issue 45, 2018

Tetraphenylethylene-based glycoclusters with aggregation-induced emission (AIE) properties as high-affinity ligands of bacterial lectins

Abstract

Tetraphenylethylene (TPE) is fluorescent through aggregation induced emission (AIE) in water. Herein, TPE was used as the core of glycoclusters that target the bacterial lectins LecA and LecB of Pseudomonas aeruginosa. Synthesis of these TPE-based glycoclusters was accomplished by using azide–alkyne “click” chemistry. The AIE properties of the resulting glycoclusters could be readily verified, but imaging could not be pursued due to the overlap of the fluorescence signals from cells and bacteria. Nonetheless, the glycoclusters displayed nanomolar affinities toward LecA and LecB. Further evaluation in a cell-based anti-adhesive assay highlighted a limited decrease in adhesion (20%) for the fucosylated glycocluster. This confirmed that these TPE-based glycoclusters are indeed LecA and LecB high-affinity ligands. Nevertheless, the hypotheses involving their application in imaging or anti-adhesive therapy could not be verified.

Graphical abstract: Tetraphenylethylene-based glycoclusters with aggregation-induced emission (AIE) properties as high-affinity ligands of bacterial lectins

Supplementary files

Article information

Article type
Paper
Submitted
20 Aug 2018
Accepted
22 Oct 2018
First published
24 Oct 2018

Org. Biomol. Chem., 2018,16, 8804-8809

Tetraphenylethylene-based glycoclusters with aggregation-induced emission (AIE) properties as high-affinity ligands of bacterial lectins

M. Donnier-Maréchal, S. Abdullayev, M. Bauduin, Y. Pascal, M. Fu, X. He, E. Gillon, A. Imberty, E. Kipnis, R. Dessein and S. Vidal, Org. Biomol. Chem., 2018, 16, 8804 DOI: 10.1039/C8OB02035C

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