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

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.