ALL libraries (COBIB.SI union bibliographic/catalogue database)
  • Synthesis of novel DC-SIGN ligands with an [alpha]-fucosylamide anchor
    Timpano, Gabriele ...
    The dendritic cell-specific intercellular adhesion molecule (ICAM) 3-grabbing nonintegrin (DC-SIGN) is a C-type lectin that appears to perform several different functions. Besides mediating adhesion ... between dendritic cells and T lymphocytes, DC-SIGN recognizes several pathogens some of which, including HIV, appear to exploit it to invade host organisms. The intriguing diversity of the roles attributed to DC-SIGN and their therapeutic implications have stimulated the search for new ligands that could be used as biological probes and possibly as lead compounds for drug development. The natural ligands of DC-SIGN consist of mannose oligosaccharides or fucose-containing Lewis-type determinants. Using the known 3D structure of the Lewis-x trisaccharide, we have identified some monovalent -fucosylamides that bind to DC-SIGN with inhibitory constants 0.4-0.5 mM, as determined by SPR, and have characterized their interaction with the protein by STD NMR spectroscopy. This work establishes for the first time -fucosylamides as functional mimics of chemically and enzymatically unstable -fucosides and describes interesting candidates for the preparation of multivalent systems able to block the receptor DC-SIGN with high affinity and with potential biomedical applications.
    Source: ChemBioChem : a European journal of chemical biology. - ISSN 1439-4227 (Vol. 9, no. 12, 2008, str. 1921-1930)
    Type of material - article, component part
    Publish date - 2008
    Language - english
    COBISS.SI-ID - 2360433

Shelf entry