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

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DOIResolve DOI: http://doi.org/10.1039/c3ob40515j
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TypeArticle
Journal titleOrganic and Biomolecular Chemistry
ISSN1477-0520
Volume11
Issue26
Pages43404349; # of pages: 10
SubjectBinding domain; Calix[5]arene; Causative agents; Cholera toxin; Epithelial cells; Inhibition assays; Multivalency effects; Valencies; Positive ions; Chemistry
AbstractCholera 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 100000 compared to a monovalent GM1os derivative, making GM1os-calix[5]arene one of the most potent known CTB inhibitors. This journal is © The Royal Society of Chemistry 2013.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Institute for Biological Sciences (IBS-ISB)
Peer reviewedYes
NPARC number21269768
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Record identifiere27d4c2a-b951-4934-9b06-cd5bc8b51466
Record created2013-12-13
Record modified2016-05-09
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