Syntheses of biotinylated alpha-galactosylceramides and their effects on the immune system and CD1 molecules

J Med Chem. 1999 May 20;42(10):1836-41. doi: 10.1021/jm990054n.

Abstract

A representative alpha-galactosylceramide (alpha-GalCer), KRN7000, has strong immunostimulatory and antitumor activity. Recent studies demonstrated that KRN7000-pulsed antigen-presenting cells (APC) can activate natural killer T (NKT) cells, a novel T-cell lineage, and CD1d molecules on APC play an important role in the activation of NKT cells. However, it remains unclear whether alpha-GalCers actually bind to CD1d molecules. To address this question, we synthesized three kinds of biotinylated alpha-GalCer and a biotinylated beta-GalCer and found that the biotinylated alpha-GalCers significantly stimulate the proliferation of murine spleen cells, but the biotinylated beta-GalCer does not and that all biotinylated compounds bind to CD1d molecules.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antigens, CD1 / metabolism*
  • Antigens, CD1d
  • Biotinylation
  • Cell Division / drug effects
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / chemistry
  • Galactosylceramides / metabolism
  • Galactosylceramides / pharmacology
  • Humans
  • Mice
  • Mice, Inbred C57BL
  • Protein Binding
  • Spleen / cytology
  • Spleen / drug effects
  • Structure-Activity Relationship
  • Surface Plasmon Resonance

Substances

  • Antigens, CD1
  • Antigens, CD1d
  • CD1D protein, human
  • Galactosylceramides