Issue 16, 2011
From the journal:

Organic & Biomolecular Chemistry

Second generation of fucose-based DC-SIGN ligands : affinity improvement and specificity versus Langerin†

Manuel Andreini,‡a   Daniela Doknic,‡a   Ieva Sutkeviciute,‡be   José J. Reina,a   Janxin Duan,c   Eric Chabrol,be   Michel Thepaut,bef   Elisabetta Moroni,a   Fabio Doro,a   Laura Belvisi,a   Joerg Weiser,c   Javier Rojo,d   Franck Fieschi*beg  and  Anna Bernardi*a  

* Corresponding authors

a Universita' degli Studi di Milano, Dipartimento di Chimica Organica e Industriale and CISI, via Venezian 21, 20133 Milano, Italy
E-mail: anna.bernardi@unimi.it

b Institut de Biologie Structurale, Université Grenoble I, 41 rue Jules Horowitz, 38027 Grenoble, France
E-mail: fieschi@ibs.fr

c Anterio consult&research, Augustaanlage 23, D-68165 Mannheim

d Glycosystems Laboratory, Instituto de Investigaciones Químicas, CSIC–Universidad de Sevilla, Américo Vespucio 49, 41092 Sevilla, Spain

e CNRS, UMR 5075, Grenoble, France

f CEA, Grenoble, France

g Institut Universitaire de France, 103 boulevard Saint-Michel, 75005 Paris, France

Abstract

DC-SIGN and Langerin are two C-type lectins involved in the initial steps of HIV infections: the former acts as a viral attachment factor and facilitates viral invasion of the immune system, the latter has a protective effect. Potential antiviral compounds targeted against DC-SIGN were synthesized using a common fucosylamide anchor. Their DC-SIGN affinity was tested by SPR and found to be similar to that of the natural ligand Lewis-X (LeX). The compounds were also found to be selective for DC-SIGN and to interact only weakly with Langerin. These molecules are potentially useful therapeutic tools against sexually transmitted HIV infection.

Graphical abstract: Second generation of fucose-based DC-SIGN ligands : affinity improvement and specificity versus Langerin

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Article information

DOI
https://doi.org/10.1039/C1OB05573A
Article type
Paper
Submitted
11 Apr 2011
Accepted
20 May 2011
First published
20 May 2011

Org. Biomol. Chem., 2011,9, 5778-5786

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Second generation of fucose-based DC-SIGN ligands : affinity improvement and specificity versus Langerin

M. Andreini, D. Doknic, I. Sutkeviciute, J. J. Reina, J. Duan, E. Chabrol, M. Thepaut, E. Moroni, F. Doro, L. Belvisi, J. Weiser, J. Rojo, F. Fieschi and A. Bernardi, Org. Biomol. Chem., 2011, 9, 5778 DOI: 10.1039/C1OB05573A

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