Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes

M. Mattarella; J. Garcia-Hartjes; T. Wennekes; H. Zuilhof; J.S. Siegel

doi:10.1039/c3ob40438b

Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes

M. Mattarella, J. Garcia-Hartjes, T. Wennekes, H. Zuilhof, J.S. Siegel

Research output: Contribution to journal › Article › Academic › peer-review

16 Citations (Scopus)

Abstract

Eight symmetric and pentavalent corannulene derivatives were functionalized with galactose and the ganglioside GM1-oligosaccharide (GM1os) via copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions. The compounds were evaluated for their ability to inhibit the binding of the pentavalent cholera toxin to its natural ligand, ganglioside GM1. In this assay, all ganglioside GM1os-sym-corannulenes proved to be highly potent nanomolar inhibitors of cholera toxin.

Original language	English
Pages (from-to)	4333-4339
Journal	Organic & Biomolecular Chemistry
Volume	11
Issue number	26
DOIs	https://doi.org/10.1039/c3ob40438b
Publication status	Published - 2013

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Keywords

heat-labile enterotoxin
receptor-binding
multivalent ligands
gm1 mimics
design
corannulene
derivatives
dendrimers
subunit

Cite this

Mattarella, M., Garcia-Hartjes, J., Wennekes, T., Zuilhof, H., & Siegel, J. S. (2013). Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes. Organic & Biomolecular Chemistry, 11(26), 4333-4339. https://doi.org/10.1039/c3ob40438b

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abstract = "Eight symmetric and pentavalent corannulene derivatives were functionalized with galactose and the ganglioside GM1-oligosaccharide (GM1os) via copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions. The compounds were evaluated for their ability to inhibit the binding of the pentavalent cholera toxin to its natural ligand, ganglioside GM1. In this assay, all ganglioside GM1os-sym-corannulenes proved to be highly potent nanomolar inhibitors of cholera toxin.",

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AU - Zuilhof, H.

AU - Siegel, J.S.

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AB - Eight symmetric and pentavalent corannulene derivatives were functionalized with galactose and the ganglioside GM1-oligosaccharide (GM1os) via copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions. The compounds were evaluated for their ability to inhibit the binding of the pentavalent cholera toxin to its natural ligand, ganglioside GM1. In this assay, all ganglioside GM1os-sym-corannulenes proved to be highly potent nanomolar inhibitors of cholera toxin.

KW - heat-labile enterotoxin

KW - receptor-binding

KW - multivalent ligands

KW - gm1 mimics

KW - design

KW - corannulene

KW - derivatives

KW - dendrimers

KW - subunit

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DO - 10.1039/c3ob40438b

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EP - 4339

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 26

ER -

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10.1039/c3ob40438b