N-(1-Adamantaneacetyl)-ceramide trihexoside

CATALOG # 1947
Amount 1 mg
Price $420.00
Qty
 
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

    References:
    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