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310500

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.

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H41NO2
CAS Number:
119567-63-4
Molecular Weight:
327.55
MDL number:
MFCD02259309
UNSPSC Code:
12352211
NACRES:
NA.77
Assay:
≥98% (TLC)
Form:
oil (Clear), waxy solid
Quality level:
100
Storage condition:
OK to freeze
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Quality Level

100

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

SMILES string

N([C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO)(C)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 (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

Preparation Note

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

Disclaimer

Toxicity: Irritant (B)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (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.

Global Trade Item Number

SKUGTIN
310500-5MG04055977216837