Understanding multivalent effects in glycosidase inhibition using C-glycoside click clusters as molecular probes

Abstract

Multivalent C-glycosides based on C60 or β-cyclodextrin cores were designed to probe the influence of inhitopes in glycosidase binding events.

Carbon-based glyco-nanoplatforms: towards the next generation of glycan-based multivalent probes

“…These results are also in line with previous reports of homogeneously or heterogeneously decorated fullerene probes with either carbohydrates or sp 2 -iminosugar glycomimetics 195,[197][198][199][200] for b-galactosidase inhibition. 188,195,201 Vicent and co-workers expanded the application of glycofullerene probes for multivalent enzyme inhibition to other enzymatic systems such as glycosyltransferases. [202][203][204] The authors showed the efficacy of the mannopyranose core structure of bacterial L,D-heptoside glycofullerenes as glycosyltransferase inhibitors in the low micromolar range (IC 50 = 7-45 mM).…”

“…These results are also in line with previous reports of homogeneously or heterogeneously decorated fullerene probes with either carbohydrates or sp 2 -iminosugar glycomimetics 195,197–200 for β-galactosidase inhibition. 188,195,201…”

Recent Advances on Multivalent Carbon Nanoform-Based Glycoconjugates

“…It is important to highlight that this feature has only been previously observed for fullerene derivatives homogeneously decorated with carbohydrates or heterogeneously functionalized with carbohydrates and sp 2 -iminosugar glycomimetics [59][60][61][62][63] against -galactosidase. 49,57,64 Vicent et al have extended the concept of multivalent enzyme inhibition to other major class of glycosyl processing enzymes, namely glycosyltransferases 65 by using multimeric glycoclusters based on fullerene as central scaffold. 66,67 In 2016, they reported the synthesis of unprecedent Kdo glycofullerenes 19-22 (Figure 5) and the enzymatic assays against therapeutically relevant bacterial heptosyltransferase I (WaaC).…”

Fullerenes in biology and medicine

“…56, 61-64 In 2013, Luczkowiak et al . 65 reported for the first time the potential application of glycodendrofullerenes as antiviral agents.…”