D-MAPP

CATALOG # 1859
Amount 100 mg
Price $210.00
Qty
 
D-MAPP
  • Catalog #:1859
  • Scientific Name:D-MAPP
  • Common Name:D-erythro-2-Tetradecanoylamino-1-phenyl-1-propanol
    Activity: alkaline ceramidase inhibitor
  • Empirical Formula:C23H39NO2
  • CAS#143492-39-1
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:361
  • Unit:100 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC
  • Solubility:ethanol
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    D-erythro-2-myristoylamino-1-phenyl-1-propanol (D-MAPP) is an inhibitor of alkaline ceramidase due to it being structurally similar to ceramide. D-erythro-MAPP has the opposite stereochemical configuration of natural D-erythroceramides which causes it to inhibit alkaline ceramidase. D-MAPP is also a poor inhibitor of acid ceramidase. The L-erythro- MAPP isomer is inactive towards ceramidase due to it having the same stereochemical configuration as natural ceramides. The inhibition of ceramidase by D-MAPP causes an elevation of ceramide levels in cells leading to growth suspension and cell cycle arrest1 but not apoptosis or TNF/IFN induced cell death.2 In cancer cell lines D-MAPP and other ceramidase inhibitors have been used to increase the levels of endogenous ceramides. The higher levels of ceramides causes an increase in the apoptotic effects following radiation of the cells.3 D-MAPP and N,N-dimethyl-sphingosine inhibit mitogen-activated protein kinase activation induced by oxidized low-density lipoproteins.4

    References:
    1. A. Bielawska et al. “(1S,2R)-D-erythro-2-(N-Myristoylamino)-1-phenyl-1-propanol as an Inhibitor of Ceramidase” The Journal of Biological Chemistry, vol. 271 pp. 12646-12654, 1996
    2. S. Payne et al. “Epidermal growth factor inhibits ceramide-induced apoptosis and lowers ceramide levels in primary placental trophoblasts” Cellular Physiology, vol. 180 pp. 263-270, 1999
    3. C. Rodriguez-Lafrasse et al. “Increasing endogenous ceramide using inhibitors of sphingolipid metabolism maximizes ionizing radiation-induced mitochondrial injury and apoptotic cell killing” International Journal of Cancer, vol. 101 pp. 589-598, 2002
    4. N. Auge et al. “Oxidized LDL-Induced Smooth Muscle Cell Proliferation Involves the EGF Receptor/PI-3 Kinase/Akt and the Sphingolipid Signaling Pathways” Athersclerosis, Thrombosis, and Vascular Biology, vol. 22 pp. 1990-1995, 2002