Synthesis and affinity evaluation of a small library of bidentate cholera toxin ligands: towards non hydrolysable ganglioside mimics
Articolo
Data di Pubblicazione:
2010
Citazione:
Synthesis and affinity evaluation of a small library of bidentate cholera toxin ligands: towards non hydrolysable ganglioside mimics / P. Cheshev, L. Morelli, M. Marchesi, Č. Podlipnik, M. Bergström, A. Bernardi. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 16:6(2010), pp. 1951-1967.
Abstract:
A small library of nonhydrolyzable mimics of GM1 ganglioside, featuring galactose and sialic acid as pharmacophoric carbohydrate residues, was synthesized and tested. All compounds were synthesized from readily available precursors using high-performance reactions, including click chemistry protocols, and avoiding O-glycosidic bonds. Some of the most active molecules also feature a point of further derivatization that can be used for conjugation with polyvalent aglycons. Their affinity towards cholera toxin was assessed by weak affinity chromatography, which allowed a systematic evaluation and selection of the best candidates. Affinity could be enhanced up to one or two orders of magnitude over the affinity of the individual pharmacophoric sugar residues.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
P. Cheshev, L. Morelli, M. Marchesi, Č. Podlipnik, M. Bergström, A. Bernardi
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