Purification and structural characterization of de-N-acetylated form of GD3 ganglioside present in human melanoma tumors

Glycobiology. 2007 Apr;17(4):367-73. doi: 10.1093/glycob/cwm006. Epub 2007 Jan 22.

Abstract

The presence of gangliosides containing de-N-acetylated sialic acids in human tissues has been so far shown by using mouse monoclonal antibodies specific for the de-N-acetylated forms, but the isolation and chemical characterization of such compounds have not yet been performed. Since indirect evidence suggested that de-N-acetylGD3 ganglioside could be present in human melanoma tumors, we analyzed the gangliosides purified from a 500-g pool of those tumors. The de-N-acetylGD3 that was found to migrate just below GD2 in thin-layer chromatography was isolated from the disialogangliosides by high-pressure liquid chromatography using the specific antibody SGR37 to monitor the elution. The amount of antigen was found to be 320 ng per gram of fresh tumor or 0.1% of total gangliosides. Gas chromatography-mass spectrometry analysis of the antibody-positive ganglioside showed that sialic acids were formed of one molecule of N-acetylneuraminic acid and one molecule of neuraminic acid. Radioactive re-N-acetylation of the antigen yielded a GD3-like ganglioside with the radioactive label on the external sialic acid. The constitutive fatty acids were found to differ markedly from those of GD3 and 9-O-acetylGD3 isolated from the same pool of tumors. The major fatty acids were C16:0 and C18:0 in de-N-acetylGD3, whereas GD3 and its 9-O-acetylated derivative contained a large amount of C24:1. These data show that de-N-acetylGD3 ganglioside is indeed present in human melanoma tumors, and the fatty acid content suggests the existence of a de-N-acetylase mostly active on the molecular species of gangliosides with short-chain fatty acids.

MeSH terms

  • Acetylation
  • Carbohydrate Conformation
  • Gangliosides / chemistry*
  • Gangliosides / isolation & purification*
  • Humans
  • Immunohistochemistry
  • Melanoma / metabolism*
  • Melanoma / pathology
  • Melanoma / surgery
  • Models, Molecular
  • N-Acetylneuraminic Acid / isolation & purification

Substances

  • Gangliosides
  • ganglioside, GD3
  • N-Acetylneuraminic Acid