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Issue 26, 2013
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Picomolar inhibition of cholera toxin by a pentavalent ganglioside GM1os-calix[5]arene

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Abstract

Cholera toxin (CT), the causative agent of cholera, displays a pentavalent binding domain that targets the oligosaccharide of ganglioside GM1 (GM1os) on the periphery of human abdominal epithelial cells. Here, we report the first GM1os-based CT inhibitor that matches the valency of the CT binding domain (CTB). This pentavalent inhibitor contains five GM1os moieties linked to a calix[5]arene scaffold. When evaluated by an inhibition assay, it achieved a picomolar inhibition potency (IC50 = 450 pM) for CTB. This represents a significant multivalency effect, with a relative inhibitory potency of 100 000 compared to a monovalent GM1os derivative, making GM1os-calix[5]arene one of the most potent known CTB inhibitors.

Graphical abstract: Picomolar inhibition of cholera toxin by a pentavalent ganglioside GM1os-calix[5]arene

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Publication details

The article was received on 13 Mar 2013, accepted on 29 Apr 2013 and first published on 20 May 2013


Article type: Paper
DOI: 10.1039/C3OB40515J
Citation: Org. Biomol. Chem., 2013,11, 4340-4349
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    Picomolar inhibition of cholera toxin by a pentavalent ganglioside GM1os-calix[5]arene

    J. Garcia-Hartjes, S. Bernardi, C. A. G. M. Weijers, T. Wennekes, M. Gilbert, F. Sansone, A. Casnati and H. Zuilhof, Org. Biomol. Chem., 2013, 11, 4340
    DOI: 10.1039/C3OB40515J

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