N-Hexanoyl-NBD-L-threo-sphingosine (1mg)

CATALOG # 1857-001
Amount 1mg
Price $650.00
Qty
 
N-Hexanoyl-NBD-L-threo-sphingosine
  • Catalog #:1857-001
  • Scientific Name:N-Hexanoyl-NBD-L-threo-sphingosine
  • Common Name:N-C6:0-NBD-Ceramide; N-C6:0-NBD-L-threo-Sphingosine
  • Empirical Formula:C30H49N5O6
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:576
  • Unit:1mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC
  • Solubility:ethanol, methanol, chloroform
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This product is a high purity, non-natural L-threo ceramide containing a fluorescent NBD label and is ideal as a standard and for biological studies. NBD (7-nitrobenzofurazan) has been shown to have only a small influence on lipid adsorption into cells and cellular membranes especially when the fatty acid is a short chain. The fluorescent analog of natural ceramide is comparable to C6:0-ceramide in many biological functions such as inhibition of VSV-G protein transport1, and transport of sphingomyelin and glucocerebroside from the golgi apparatus to the cell surface.2 Both the natural D-erythro and the nonnatural L-erythro and the D- and L-threo ceramides display similar effectiveness in inducing apoptotic damage in cells.3 The protein phosphatases PP1 and PP2A, which are involved in regulating apoptosis and cell growth, are activated by D-erythro ceramide but inhibited by L-threo, D-threo, and L-erythro ceramide.4 Both D-erythro and D-threo C2 ceramides have been found to be potent inducers of IL-6 production, while neither the L-threo or L-erythro stereoisomers of ceramide were effective.5 D- and L-erythro ceramide and D- and L-threo ceramide are also comparably effective inhibitors of protein kinase C.6

    References:
    1. A. Rosenwald and R. Pagano “Inhibition of glycoprotein traffic through the secretory pathway by ceramide” Journal of Biological Chemistry, Vol. 268 pp. 4577-4579, 1993
    2. N. Lipsky, R. Pagano “Intracellular translocation of fluorescent sphingolipids in cultured fibroblasts: Endogenously synthesized sphingomyelin and glucocerebroside analogues pass through the golgi apparatus en route to the plasma membrane” Journal of Cell Biology, Vol. 100 pp. 27-34, 1985
    3. W. Jarvis et al. “Induction of Apoptosis and Potentiation of Ceramide-mediated Cytotoxicity by Sphingoid Bases in Human Myeloid Leukemia Cells” The Journal of Biological Chemistry, Vol. 271 pp. 8275-8284, 1996
    4. C. Chalfant et al. “Long Chain Ceramides Activate Protein Phosphatase-1 and Protein Phosphatase-2A Activation is Stereospecific and Regulated by Phosphatidic Acid” The Journal of Biological Chemistry, Vol. 274 pp. 20313-20317, 1999
    5. S. Laulederkind et al. “Ceramide Induces Interleukin 6 Gene Expression in Human Fibroblasts” The Journal of Experimental Medicine, Vol. 182 pp. 599-604, 1995