N-(1-Adamantaneacetyl)-glucosylceramide

CATALOG # 1945
Amount 5 mg
Price $420.00
Qty
 
N-(1-Adamantaneacetyl)-glucosylceramide
  • Catalog #:1945
  • Scientific Name:N-(1-Adamantaneacetyl)-glucosylceramide
  • Common Name:N-(1-Adamantaneacetyl)-glucocerebroside
    Activity: Inhibitor of glucocerebrosidase and lactosylceramide synthase
  • Empirical Formula:C36H61NO8
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:636
  • Unit:5 mg
  • Solvent:none
  • Source:semisynthetic
  • Purity:98+%
  • Analytical Methods:TLC; identity confirmed by MS
  • Natural Source:plant
  • Melting Point:n/a
  • Solubility:chloroform, methanol, chloroform/methanol 9:1
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    N-(1-Adamantaneacetyl)-glucosylceramide (AdaGlcCer) is a water soluble analog of glucosylceramide that demonstrates unique properties as compared with its natural substrate. Glucocerebroside is a critical compound in cells due to its function as the biosynthetic precursor of lactosylceramide and from there of most of the neutral oligoglycolipids and gangliosides.1 Glucocerebroside is also important in its cellular functions such as its ability to modulate membrane traffic along the endocytic pathway.2 Glycosphingolipids containing adamantane acetic acid demonstrate increased water solubility, making them more amphipathic and, in part, mimic glycosphingolipid membrane receptor function in solution.3 AdaGlcCer is an effective inhibitor of glucocerebrosidase and is able to promote an accumulation of glycosphingolipids in cells.4 The adamantane acetic acid derivative of galactosylceramide has been shown to stimulate glucocerebrosidase at pH 5 although not at pH 7. The adamantane acetic acid derivatives of both glucosyl and galactosylceramide correct the N370S mutant glucocerebrosidase traffic from ER to lysosomes. Adamantyl galactosylceramide decreases the levels of glucosylceramides in both normal and lysosomal storage disease cells making it a potential therapeutic treatment for lysosomal disorders. Adamantyl glucosylceramide inhibits lactosylceramide synthase causing an accumulation of glucosylceramide and a decrease in other glycosphingolipids. Adamantyl galactosylceramide inhibits the formation of Gb3 and Gb4 by a substrate inhibition of Gb3 synthase making it a potential therapeutic treatment for Fabry disease. Adamantyl galactosylceramide also inhibits sulfatide formation in cells.

    References:
    1. D. Sillence et al. “Assay for the transbilayer distribution of glycolipids: selective oxidation of glucosylceramide to glucuronylceramide by TEMPO nitroxyl radicals” Journal of Lipid Research, Vol. 41(8) pp. 1252-1260, 2000
    2. D. Sillence et al. “Glucosylceramide modulates membrane traffic along the endocytic pathway” Journal of Lipid Research, Vol. 43(11) pp. 1837-1845, 2002
    3. C. Lingwood et al. “Soluble adamantyl glycosphingolipid analogs as probes of glycosphingolipid function” Methods Mol Biol., Vol. 347 pp. 305-320, 2006
    4. C. Lingwood et al. “Adamantyl glycosphingolipids provide a new approach to the selective regulation of cellular glycosphingolipid metabolism” The Journal of Biological Chemistry, Vol. 286(24) pp. 21413-21426, 2011