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Merck

341207

ET-18-OCH3

A cell-permeable and reversible cytotoxic agent that shows selective cytocidal activity against neoplastic cells and virally transformed cells.

Sinónimos:

ET-18-OCH3, Edelfosine, 1-O-Octadecyl-2-O-methyl- rac-glycero-3-phosphorylcholine, Edelfosine, 1-O-Octadecyl-2-O-methyl-rac-glycero-3-phosphorylcholine

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Fórmula empírica (notación de Hill):
C27H58NO6P
Número CAS:
Peso molecular:
523.73
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥95% (TLC)
Form:
solid
Quality level:
Storage condition:
OK to freeze
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Quality Level

description

RTECS - YK0718000

assay

≥95% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

DMSO: 5 mg/mL, ethanol: 5 mg/mL, chloroform: 50 mg/mL, water: soluble

shipped in

ambient

storage temp.

−20°C

SMILES string

[P](=O)([O-])(OCC[N+](C)(C)C)OCC(OC)COCCCCCCCCCCCCCCCCCC

InChI

1S/C27H58NO6P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-32-25-27(31-5)26-34-35(29,30)33-24-22-28(2,3)4/h27H,6-26H2,1-5H3

InChI key

MHFRGQHAERHWKZ-UHFFFAOYSA-N

General description

A cell-permeable and reversible cytotoxic agent that shows selective cytocidal activity against neoplastic cells and virally transformed cells. Selectively inhibits phosphatidylinositol-specific phospholipase C (PI-PLC, IC50 = 9.6 µM) but does not inhibit phosphatidylcholine-specific PLC or PLD. Promotes apoptosis in mitogen-activated, but not resting, T lymphocytes in a dose- and time-dependent manner. Also promotes rapid and selective apoptosis in human leukemic cells.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
PI-PLC
Product does not compete with ATP.
Reversible: yes
Target IC50: 9.6 µM against phosphatidylinositol-specific phospholipase C (PI-PLC)

Preparation Note

Following reconstitution in ethanol, aliquot and freeze (-20°C). Ethanol stock solutions are stable for up to 3 months at -20°C. Unstable in aqueous solution; reconstitute just prior to use.

Other Notes

Harguindey, J., et al. 2000. Apoptosis5, 87.
Cabaner, C., et al. 1999. Br. J. Pharmacol. 127, 813.
Powis, G., and Phil, D. 1994. Cancer Metastasis Rev.13, 91.
Helfman, D., et al. 1993. Cancer Res. 53, 2955.
Mollinedo, F., et al. 1993. Biochem. Biophys. Res. Commun. 192, 603.
Powis, G., et al. 1992. Cancer Res.52, 2835.
Oishi, K., et al. 1988. Biochem. Biophys. Res. Commun.157, 1000.

Legal Information

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

Disclaimer

Material may form micelles in aqueous stock solutions, which may affect experimental results.
Toxicity: Carcinogenic / Teratogenic (D)


Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Contenido relacionado

Human Kinome Poster: The InhibitorSelect™ Protein Kinase Inhibitor Libraries provide broad coverage of the human kinome as shown here. The depicted human kinome dendrogram of 518 kinases are classified into five broad groups, 90 families, and 145 subfamilies. Inhibitor coverage was assigned based upon published data related to potency (IC50, EC50, Kd, etc.) for individual kinases harvested from the literature. Colored dots denote which library contains an inhibitor with demonstrated potent activity against the designated kinase and do not necessarily reflect known specificity of the inhibitor. Coverage of lipid and atypical kinases are depicted as a separate dendrogram. As shown, Calbiochem® Protein Kinase Inhibitor Libraries cover all major kinase families including TK, CMGC, CAMK, AGC, CK1, STE, TKL, as well as Lipid or Atypical kinase families.