376650

D-erythro-Sphingosine, N-Hexanoyl-

Biologically active, cell-permeable, non-physiological ceramide analog.

• Synonym(e): D-erythro-Sphingosine, N-Hexanoyl-, C₆ Ceramide
• Empirische Formel (Hill-System): C₂₄H₄₇NO₃
• CAS-Nummer: 124753-97-5
• Molekulargewicht: 397.63
• UNSPSC Code: 12352211
• NACRES: NA.77
• MDL number: MFCD00870174
• Assay: ≥98% (TLC)
• Form: waxy solid
• Storage condition: OK to freeze

Eigenschaften

• Quality Segment: 100
• assay: ≥98% (TLC)
• form: waxy solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: ethanol: 25 mg/mL, DMSO: soluble
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: N(C(C(O)\C=C\CCCCCCCCCCCCC)CO)C(=O)CCCCC
• InChI: 1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+
• InChI key: NPRJSFWNFTXXQC-VHEBQXMUSA-N

Beschreibung

General description

Biologically active, cell-permeable, non-physiological ceramide analog. Induces a dramatic arrest in the G₀/G₁ phase of the cell cycle. Activates MAP kinase. Activates protein phosphatase 2A (PP2A) at 10 nM. Inhibits diacylglycerol accumulation and phospholipase D (PLD) activation in fibroblasts. Induces apoptosis in MOLT-4 leukemia cells.

Biologically active, cell-permeable, nonphysiological ceramide analog. Stimulates cytosolic serine/threonine protein phosphatase in T9 cells and induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase. Induces a dramatic arrest in the G_o/G₁ phase of the cell cycle. Activates MAP kinase. Activates protein phosphatase 2A (PP2A) at 10 nM. Inhibits diacylglycerol accumulation and phospholipase D activation in fibroblasts. Induces apoptosis in Molt-4 leukemia cells.

Biochem/physiol Actions

Cell permeable: yes

Effective concentration: 10 nM in activating protein phosphatase 2A (PP2A)

Primary Target
MAP kinase, protein phosphatase 2A (PP2A)

Product does not compete with ATP.

Reversible: no

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.

Other Notes

Jayadev, S., et al. 1995. J. Biol. Chem. 270, 2047.
Venable, M.E., et al. 1994. J. Biol. Chem. 269, 26040.
Dobrowsky, R.T., et al. 1993. J. Biol. Chem. 268, 15523.
Raines, M.A., et al. 1993. J. Biol. Chem.268, 14572.
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)

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable