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.
别名:
D-erythro-Sphingosine, N,N-Dimethyl-, DMS, SK Inhibitor III, Sphingosine Kinase Inhibitor III
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关于此项目
经验公式（希尔记法）:
C20H41NO2
化学文摘社编号:
分子量:
327.55
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.77
产品名称
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.
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
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
Quality Level
Biochem/physiol Actions
Cell permeable: yes
Primary Target
PKC
PKC
Product does not compete with ATP.
Reversible: yes
Target IC50: 12 µM against PKC
Disclaimer
Toxicity: Irritant (B)
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.
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.
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.
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 weeks at -20°C.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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