Glycoside and peptide clustering around the octasilsesquioxane scaffold via photoinduced free-radical thiol-ene coupling. The observation of a striking glycoside cluster effect.
Two series of multivalent octasilsesquioxane glyco- and peptido-conjugates were synthesized using the photoinduced free-radical thiol-ene coupling (TEC). The first series was obtained by coupling C-glycosylpropyl thiols and cysteine contg. peptides with the known octavinyl octasilsesquioxane, while the second series was obtained by reacting glycosyl thiols with a new octasilsesquioxane deriv. displaying eight PEGylated chains functionalized with terminal allyl groups. The evaluation of the binding properties of mannoside and glucoside clusters toward Con A by Enzyme-Linked Lectin Assay (ELLA) revealed a modest glycoside cluster effect. However, the PEGylated POSS-based glycocluster featuring eight N-acetyl-glucosamine residues showed high affinity toward Wheat Germ Agglutinin to give a measured IC50 at 3 nM. The calcd. relative potency per no. of sugar unit (rp/n) was superior to a value of 106, thus revealing the occurrence of a striking glycoside cluster effect. [on SciFinder(R)]
Références
- Titre
- Glycoside and peptide clustering around the octasilsesquioxane scaffold via photoinduced free-radical thiol-ene coupling. The observation of a striking glycoside cluster effect.
- Type de publication
- Article de revue
- Année de publication
- 2012
- Auteurs
- Conte, Mauro Lo, Staderini Samuele, Chambery Angela, Berthet Nathalie, Dumy Pascal, Renaudet Olivier, Marra Alberto, and Dondoni Alessandro.
- Revue
- Org. Biomol. Chem.
- Volume
- 10
- Pagination
- 3269–3277
- ISSN
- 1477-0520
Soumis le 12 avril 2018