Synthesis of a novel alpha-galactosyl ceramide haptenated-lipid antigen, a useful tool in demonstrating the involvement of iNKT cells in the production of antilipid antibodies

Bioconjug Chem. 2010 Apr 21;21(4):741-7. doi: 10.1021/bc9005255.


A new haptenated derivative of alpha-galactosyl ceramide (alpha-GalCer) has been synthesized to assist in the study of the mechanism of T cell help for the production of B cell antibodies. Our synthetic route provides access to an amine intermediate which can easily be extended to generate an array of compounds, useful in various ongoing studies. Herein, we also describe the biological evaluation of the nitrophenyl (NP) haptenated alpha-GalCer and demonstrate its importance in such mechanistic studies. For instance, in vitro studies showed that NP-alpha-GalCer stimulates both T and B cell proliferation while in vivo studies in immunized mice showed the production of IgG anti-NP antibodies after exposure to NP-alpha-GalCer. The interpretation of these results helps toward a better understanding of T cell help for the production of antibodies.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antibodies / chemistry
  • Antibodies / immunology*
  • Antigens / chemistry
  • Antigens / immunology*
  • Antigens / pharmacology
  • B-Lymphocytes / immunology
  • Cell Proliferation / drug effects
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / immunology*
  • Galactosylceramides / pharmacology
  • Immunoglobulin G / immunology
  • Lipids / chemical synthesis
  • Lipids / immunology*
  • Lipids / pharmacology
  • Mice
  • Molecular Structure
  • Natural Killer T-Cells / drug effects
  • Natural Killer T-Cells / immunology*
  • Structure-Activity Relationship


  • Antibodies
  • Antigens
  • Galactosylceramides
  • Immunoglobulin G
  • Lipids