Issue 14, 2004
From the journal:

Organic & Biomolecular Chemistry

Synthesis and cholera toxin binding properties of multivalent GM1 mimics†

Daniela Arosio,ab   Ioannis Vrasidas,ab   Paola Valentini,b   Rob M. J. Liskamp,b   Roland J. Pieters*b  and  Anna Bernardi*a  

* Corresponding authors

a Dipartmento di Chimica Organica e Industriale, via Venezian 21, 20133 Milano, Italy
Fax: +39-02-50314092
Tel: anna.bernardi@unimi.it

b Department of Medicinal Chemistry, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, PO Box 80082, NL-3508 TB Utrecht, The Netherlands
E-mail: r.j.pieters@pharm.uu.nl
Fax: +31-30-253 6655

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.

Graphical abstract: Synthesis and cholera toxin binding properties of multivalent GM1 mimics

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Article information

DOI
https://doi.org/10.1039/B405344C
Article type
Paper
Submitted
13 Apr 2004
Accepted
26 May 2004
First published
30 Jun 2004

Org. Biomol. Chem., 2004,2, 2113-2124

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Synthesis and cholera toxin binding properties of multivalent GM1 mimics

D. Arosio, I. Vrasidas, P. Valentini, R. M. J. Liskamp, R. J. Pieters and A. Bernardi, Org. Biomol. Chem., 2004, 2, 2113 DOI: 10.1039/B405344C

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