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Título: | Polyvalent: C-glycomimetics based on l-fucose or d-mannose as potent DC-SIGN antagonists |
Autor: | Bertolotti, Benedetta; Sutkeviciute, Ieva; Ambrosini, Martino; Ribeiro-Viana, Renato CSIC ORCID; Rojo, Francisco Javier ; Fieschi, Franck; Dvořáková, Hana; Kašáková, Martina; Parkan, Kamil; Hlaváčková, Martina; Nováková, Kateřina; Moravcová, Jitka | Fecha de publicación: | 14-may-2017 | Editor: | Royal Society of Chemistry (UK) | Citación: | Organic and Biomolecular Chemistry 15(18): 3995-4004 (2017) | Resumen: | The C-Type lectin DC-SIGN expressed on immature dendritic cells is a promising target for antiviral drug development. Previously, we have demonstrated that mono-and divalent C-glycosides based on d-manno and l-fuco configurations are promising DC-SIGN ligands. Here, we described the convergent synthesis of C-glycoside dendrimers decorated with 4, 6, 9, and 12 α-l-fucopyranosyl units and with 9 and 12 α-d-mannopyranosyl units. Their affinity against DC-SIGN was assessed by surface plasmon resonance (SPR) assays. For comparison, parent O-glycosidic dendrimers were synthesized and tested, as well. A clear increase of both affinity and multivalency effect was observed for C-glycomimetics of both types (mannose and fucose). However, when dodecavalent C-glycosidic dendrimers were compared, there was no difference in affinity regarding the sugar unit (l-fuco, IC 17 μM; d-manno, IC 12 μM). For the rest of glycodendrimers with l-fucose or d-mannose attached by the O-or C-glycosidic linkage, C-glycosidic dendrimers were significantly more active. These results show that in addition to the expected physiological stability, the biological activity of C-glycoside mimetics is higher in comparison to the corresponding O-glycosides and therefore these glycomimetic multivalent systems represent potentially promising candidates for targeting DC-SIGN. | Versión del editor: | http://doi.org/10.1039/C7OB00322F | URI: | http://hdl.handle.net/10261/190532 | DOI: | 10.1039/c7ob00322f | ISSN: | 1477-0520 | E-ISSN: | 1477-0539 |
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