N-(1-Adamantaneacetyl)-ceramide trihexoside

CATALOG # 1947
Amount 1 mg
Price $420.00
N-(1-Adamantaneacetyl)-ceramide trihexoside
  • Catalog #:1947
  • Scientific Name:N-(1-Adamantaneacetyl)-ceramide trihexoside
  • Common Name:N-Adamantyl-globotriaosylceramide; AdaGb3
  • Empirical Formula:C48H83NO18
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:962
  • Unit:1 mg
  • Source:semisynthetic
  • Purity:98+%
  • Analytical Methods:TLC; identity confirmed by MS
  • Natural Source:porcine
  • Solubility:chloroform/methanol, 2:1, methanol, DMF
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    N-(1-Adamantaneacetyl)-ceramide trihexoside (adaGb3) is a water soluble analog of ceramide trihexoside (globotriaosylceramide, Gb3) that demonstrates unique properties as compared with its natural substrate. By replacing the natural fatty acyl group of the ceramide with a rigid, three dimensional hydrocarbon frame, a novel class of glycosphingolipids is produced which demonstrates similar toxin interactions to natural glycosphingolipids but increased water solubility. Unlike the water-soluble lipid-free Gb3 oligosaccharide, adaGb3 retains high affinity for verotoxin binding in aqueous solutions and also shares some properties of Gb3-cholesterol complexes in solution which may relate to its several bioactivities.1,2 AdaGb3 has also been shown to functionally mimic Gb3 microdomains, providing a new class of molecular tools for studying the role of glycolipids and lipid rafts in such areas as HIV-1 fusion and other biological processes. AdaGb3 may be able to disrupt HIV gp120-glycolipid interactions, thereby obviating the problem of resistance mutants selected by current antiretroviral treatments and opening a new route for controlling HIV-1 replication in infected individuals.3 AdaGb3 has recently been proposed as a regulator for multidrug resistance in cancer cells by taking advantage of the interaction between Gb3 and the glycoprotein MDR1, thus modulating the function of MDR1 across the intestinal endothelium.4

    1. C. Lingwood et al., Adamantyl Glycosphingolipids Provide a New Approach to the Selective Regulation of Cellular Glycosphingolipid Metabolism. The Journal of Biological Chemistry 286:24 (2011) 21413-21426
    2. M. Mylvaganam and C. Lingwood, Adamantyl Globotriaosyl Ceramide: A Monovalent Soluble Mimic Which Inhibits Verotoxin Binding to Its Glycolipid Receptor. Biochemical and Biophysical Research Communications 257:2 (1999) 391-394
    3. J. Fantini et al., A novel soluble analog of the HIV-1 fusion cofactor, globotriaosylceramide (Gb3 ), eliminates the cholesterol requirement for high affinity gp120/Gb 3 interaction. Journal of Lipid Research 43 (2002) 1670-1679
    4. C. Lingwood et al., Inhibition of multidrug resistance by adamantylgb3, a globotriaosylceramide analog. Journal of Biological Chemistry 283 (2008) 4501-4511