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CATALOG # 1857


  • Catalog #:1857
  • 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
  • CAS#:114301-95-0
  • SDS:View Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:576
  • Unit:100 µg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC
  • Solubility:ethanol, methanol, chloroform
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No


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

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
Price $268.00

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Catalog #: 1857-001
CAS#: 114301-95-0
Unit: 1mg

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