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Key Documents

310500

Sigma-Aldrich

D-erythro-Sphingosine, N,N-Dimethyl-

A cell-permeable and reversible inhibitor of protein kinase C (PKC; IC₅₀ = 12 µM) and stimulates Src kinase activity.

Sinónimos:

D-erythro-Sphingosine, N,N-Dimethyl-, DMS, SK Inhibitor III, Sphingosine Kinase Inhibitor III

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About This Item

Fórmula empírica (notación de Hill):
C20H41NO2
Número de CAS:
Peso molecular:
327.55
UNSPSC Code:
12352211
NACRES:
NA.77

Quality Level

assay

≥98% (TLC)

form

oil (Clear)
waxy solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

solubility

DMSO: 5 mg/mL
ethanol: soluble
methanol: soluble

shipped in

ambient

storage temp.

−20°C

InChI

1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1

InChI key

YRXOQXUDKDCXME-YIVRLKKSSA-N

General description

A cell-permeable and reversible inhibitor of protein kinase C (IC50 = 12 µM) and enhances src kinase activity. Useful for inhibiting cell surface expression of selectins that promote adhesion of leukocytes or tumor cells to platelets and endothelial cells. Induces apoptosis in human leukemia HL-60 cells.
A cell-permeable and reversible inhibitor of protein kinase C (PKC; IC50 = 12 µM) and stimulates Src kinase activity. Useful for inhibiting cell surface expression of selectins that promote adhesion of leukocytes or tumor cells to platelets and endothelial cells. Induces apoptosis in human leukemia HL-60 cells. An inhibitor of sphingosine kinase.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
PKC
Product does not compete with ATP.
Reversible: yes
Target IC50: 12 µM against PKC

Warning

Toxicity: Irritant (B)

Reconstitution

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

Other Notes

Cuvillier, O., et al. 1996. Nature381, 800.
Ohta, H., et al. 1995. Cancer Res.55, 691.
Kimura, S., et al. 1992. Biochem. Pharmacol.44, 1585.
Hanada, K., et al. 1991. Biochemistry30, 11682.
Igarashi, Y., et al. 1990. J. Biol. Chem.265, 5385.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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Grégory Lavieu et al.
Methods in molecular biology (Clifton, N.J.), 445, 159-173 (2008-04-22)
Sphingolipids are constituents of biological membranes. Ceramide and sphingosine 1-phosphate (S1P) also act as second messengers and are part of a rheostat system, in which ceramide promotes cell death and growth arrest, and S1P induces proliferation and maintains cell survival.

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