N-(1-Adamantaneacetyl)-galactosylceramide

CATALOG # 1946
Amount 5 mg
Price $420.00
Qty
 
N-(1-Adamantaneacetyl)-galactosylceramide
  • Catalog #:1946
  • Scientific Name:N-(1-Adamantaneacetyl)-galactosylceramide
  • Common Name:N-(1-Adamantaneacetyl)-galactocerebroside
    Activity: Inhibitor of glucosylceramide, sulfatide, and globotriaosylceramide (Gb3) synthesis
  • Empirical Formula:C36H63NO8
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:638
  • Unit:5 mg
  • Solvent:none
  • Source:semisynthetic
  • Purity:98+%
  • Analytical Methods:TLC; identity confirmed by MS
  • Natural Source:bovine
  • 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)-galactosylceramide is a water soluble analog of galactosylceramide that demonstrates unique properties as compared with its natural substrate. Galactocerebrosides are found primarily in neuronal tissues and are the major glycosphingolipids in the central nervous system. They are the largest single component of the myelin sheath of nerves and act to form part of the structural support of the myelin sheath.1 Cerebrosides are involved in a very wide range of biological activities such as cell agglutination, intracellular communication, cellular development, and antitumor/cytotoxic effects.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 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 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 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. M. Sheldon, D.Lyudmila, “Cycloserine-induced decrease of cerebroside in myelin” Lipids, Vol. 33:4 pp. 441-443, 1998
    2. X. Zhou, L. Tang and Y. Liu “An Isomeric Mixture of Novel Cerebrosides Isolated from Impatiens pritzellii Reduces Lipopolysaccharide-Induced Release of IL-18 from Human Peripheral Blood Mononuclear Cells” Lipids, Vol. 44:8 pp. 759-763, 2009
    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