110145
D-erythro-Sphingosine, N-Acetyl-
Biologically active, cell-permeable, non-physiological ceramide analog.
Synonym(s):
D-erythro-Sphingosine, N-Acetyl-, C2 Ceramide
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About This Item
Empirical Formula (Hill Notation):
C20H39NO3
CAS Number:
Molecular Weight:
341.53
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.77
Assay:
≥98% (TLC)
Form:
solid
Storage condition:
OK to freeze
Quality Segment
assay
≥98% (TLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
color
white to off-white
solubility
DMSO: 25 mg/mL, ethanol: 5 mg/mL, methanol: 5 mg/mL
shipped in
ambient
storage temp.
−20°C
SMILES string
N([C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO)C(=O)C
InChI
1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20+/m0/s1
InChI key
BLTCBVOJNNKFKC-QUDYQQOWSA-N
General description
Biologically active, cell-permeable, non-physiological ceramide analog. Inhibits cell growth and induces apoptosis in HL-60 cells. Induces intranucleosomal DNA fragmentation. An activator of heterotrimeric protein phosphatase 2A (PP2A). Stimulates a cytosolic serine/threonine protein phosphatase in T9 cells at concentrations as low as 100 nM. Activates stress activated protein kinase (SAPK) in HL-60 human promyelocytic cells.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
Inhibits cell growth and induces apoptosis in HL-60 cells
Inhibits cell growth and induces apoptosis in HL-60 cells
Product does not compete with ATP.
Reversible: no
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 1 month at -20°C. Alcohol stock solutions are stable for <1 week at -20°C.
When diluting into aqueous solution, sonication may be necessary to achieve a uniform suspension.
Other Notes
Westwick, J.K., et al. 1995. J. Biol. Chem.270, 22689.
Cifone, M.G., et al. 1994. J. Exp. Med.180, 1547.
Hannun, Y.A. 1994. J. Biol. Chem. 269, 3125.
Bielawska, A., et al. 1993. J. Biol. Chem.268, 26226.
Obeid, L.M., et al. 1993. Science259, 1769.
Ballou, L.R., et al. 1992. J. Biol. Chem.267, 20044.
Dobrowsky, R.T., and Hannun, Y.A. 1992. J. Biol. Chem.267, 5048.
Cifone, M.G., et al. 1994. J. Exp. Med.180, 1547.
Hannun, Y.A. 1994. J. Biol. Chem. 269, 3125.
Bielawska, A., et al. 1993. J. Biol. Chem.268, 26226.
Obeid, L.M., et al. 1993. Science259, 1769.
Ballou, L.R., et al. 1992. J. Biol. Chem.267, 20044.
Dobrowsky, R.T., and Hannun, Y.A. 1992. J. Biol. Chem.267, 5048.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Irritant (B)
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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