The design and preparation of carbohydrate ligands for DC-SIGN is a topic of high interest because of the role played by this Ctype lectin in immunity and infection processes. The low chemical stability of carbohydrates against enzymatic hydrolysis by glycosylases has stimulated the search for new alternatives more stable in vivo. Herein, we present a good alternative for a DCSIGN ligand based on a mannobioside mimic with a higher enzymatic stability than the corresponding disaccharide. NMR and docking studies have been performed to study the interaction of this mimic with DC-SIGN in solution demonstrating that this pseudomannobioside is a good ligand for this lectin. In vitro studies using an infection model with Ebola pseudotyped virus demonstrates that this compound presents an antiviral activity even better than the corresponding disaccharide and could be an interesting ligand to prepare multivalent systems with higher affinities for DC-SIGN with potential biomedical applications.

1,2-Mannobioside Mimic : synthesis, DC-SIGN Interaction by NMR and Docking, and Antiviral Activity / J.J. Reina, S. Sattin, D. Invernizzi, S. Mari, L. Martinez-Prats, G. Tabarani, F. Fieschi, R. Delgado, P.M. Nieto, J. Rojo, A. Bernardi. - In: CHEMMEDCHEM. - ISSN 1860-7179. - 2:7(2007), pp. 1030-1036.

1,2-Mannobioside Mimic : synthesis, DC-SIGN Interaction by NMR and Docking, and Antiviral Activity

S. Sattin
Secondo
;
D. Invernizzi;S. Mari;A. Bernardi
Ultimo
2007

Abstract

The design and preparation of carbohydrate ligands for DC-SIGN is a topic of high interest because of the role played by this Ctype lectin in immunity and infection processes. The low chemical stability of carbohydrates against enzymatic hydrolysis by glycosylases has stimulated the search for new alternatives more stable in vivo. Herein, we present a good alternative for a DCSIGN ligand based on a mannobioside mimic with a higher enzymatic stability than the corresponding disaccharide. NMR and docking studies have been performed to study the interaction of this mimic with DC-SIGN in solution demonstrating that this pseudomannobioside is a good ligand for this lectin. In vitro studies using an infection model with Ebola pseudotyped virus demonstrates that this compound presents an antiviral activity even better than the corresponding disaccharide and could be an interesting ligand to prepare multivalent systems with higher affinities for DC-SIGN with potential biomedical applications.
antiviral activity ; carbohydrate mimics ; DC-SIGN ; docking ; mannose
Settore CHIM/06 - Chimica Organica
http://www3.interscience.wiley.com/cgi-bin/fulltext/114263950/PDFSTART
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/40065
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