Towards multivalent CD1d ligands: synthesis and biological activity of homodimeric α-galactosyl ceramide analogues

Carbohydr Res. 2012 Jul 15;356(9-10):152-62. doi: 10.1016/j.carres.2012.02.034. Epub 2012 Mar 7.

Abstract

A library of dimeric CD1d ligands, containing two α-galactosyl ceramide (α-GalCer) units linked by spacers of varying lengths has been synthesised. The key dimerisation reactions were carried out via copper-catalysed click reactions between a 6"-azido-6"-deoxy-α-galactosyl ceramide derivative and various diynes. Each α-GalCer dimer was tested for its ability to stimulate iNKT cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antigens, CD1d / chemistry*
  • Antigens, CD1d / immunology
  • Carbohydrate Conformation
  • Catalysis
  • Cells, Cultured
  • Click Chemistry
  • Dimerization
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / pharmacology
  • Injections, Intravenous
  • Interferon-gamma / blood
  • Interferon-gamma / immunology
  • Ligands
  • Mice
  • Mice, Inbred C57BL
  • Models, Molecular
  • Natural Killer T-Cells / cytology
  • Natural Killer T-Cells / drug effects*
  • Natural Killer T-Cells / immunology
  • Protein Binding
  • Small Molecule Libraries / chemical synthesis*
  • Small Molecule Libraries / pharmacology
  • Spleen / cytology
  • Spleen / drug effects*
  • Spleen / immunology

Substances

  • Antigens, CD1d
  • Galactosylceramides
  • Ligands
  • Small Molecule Libraries
  • Interferon-gamma