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N,N-Dimethyl-D-erythro-sphingosine (Inhibitor of Phosphokinase C)

CATALOG # 1320

Specifications

  • Catalog #:1320
  • Scientific Name:N,N-Dimethyl-D-erythro-sphingosine (Inhibitor of Phosphokinase C)
  • Common Name:N,N-Dimethylsphingosine
  • Empirical Formula:C20H41NO2
  • CAS#:119567-63-4
  • SDS:View Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:328
  • Unit:5 mg/ml, 1ml
  • Solvent:isopropanol
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC; identity confirmed by MS
  • Solubility:ethanol, isopropanol, chloroform, methanol
  • Physical Appearance:liquid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:Yes

Description

Application Notes:

N,N-Dimethylsphingosine is a potent and specific inhibitor of sphingosine kinase, the key enzyme in the phosphorylation of sphingosine to sphingosine-1-phosphate. It has also been reported to inhibit protein kinase C (another enzyme that is responsible for phosphorylating amino acids) in certain types of cells.1 It induces apoptosis (including in a number of cancer cell lines), possibly due to the inhibition of sphingosine-1-phosphate synthesis and the resulting increase in ceramides. It acts as a stereospecific enhancer for epidermal growth factor receptor kinase.2 At very low doses N,N-dimethylsphingosine protects the heart against ischemia/reperfusion injury due to its activating sphingosine kinase (via PKCε) which is critical for myocardial ischemic preconditioning.3 It can help prevent neointimal hyperplasia, which may be the result of inhibiting ERK-1/2 and Akt signalling, and modulation of smooth muscle growth.4

References:
1. J. Kim et al. “Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases” Bioorg Med Chem, Vol. 13 pp. 3475-3485, 2005
2. Y. Igarashi et al. “A Specific Enhancing Effect of N,N-Dimethylsphingosine on Epidermal Growth Factor Receptor Autophosphorylation” Journal of Biological Chemistry, Vol. 265(10) pp. 5385-5389, 1990
3. Z. Jin and J. Karliner “Low dose N, N-dimethylsphingosine is cardioprotective and activates cytosolic sphingosine kinase by a PKC dependent mechanism” Journal of Cardiovascular Research, Vol. 71(4) pp. 725-734, 2006
4. R. McDonald et al. “The sphingosine kinase inhibitor N,N-dimethylsphingosine inhibits neointimal hyperplasia” British Journal of Pharmacology, Vol. 159(3) pp. 543-553, 2010
Price $161.00

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