Synthesis and cholera toxin binding properties of multivalent GM1 mimicsElectronic supplementary information (ESI) available: characterization of the polyvalent compounds ? imide by-products. See http://www.rsc.org/suppdata/ob/b4/b405344c/

Arosio, D., Vrasidas, I., Valentini, P., Liskamp, R.M.J. , Pieters, R.J. and Bernardi, A. (2004) Synthesis and cholera toxin binding properties of multivalent GM1 mimicsElectronic supplementary information (ESI) available: characterization of the polyvalent compounds ? imide by-products. See http://www.rsc.org/suppdata/ob/b4/b405344c/. Organic and Biomolecular Chemistry, 2(14), p. 2113. (doi:10.1039/b405344c)

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Publisher's URL: http://dx.doi.org/10.1039/b405344c

Abstract

Dendrimers based on the 3,5-di-(2-aminoethoxy)-benzoic acid branching unit were used to attach multiple copies of a GM1 mimic for inhibition of cholera toxin binding. Systems up to octavalent were synthesized along with relevant reference compounds that contained in one case the ligand in a monovalent format and in another case the scaffold but not the ligand. Using a surface plasmon resonance inhibition assay the prepared inhibitors showed good inhibition. While the monovalent GM1 mimic showed the expected inhibition in the 200 µM range the multivalent scaffolds led to increased binding. The tetravalent compound was shown to be 440-fold more potent than its monovalent counterpart. The octavalent analog, however, was the most potent compound as determined using an ELISA assay.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Arosio, D., Vrasidas, I., Valentini, P., Liskamp, R.M.J., Pieters, R.J., and Bernardi, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
ISSN:1477-0520
ISSN (Online):1477-0539

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