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341207

Sigma-Aldrich

ET-18-OCH3

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

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Synonym(s):
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
Empirical Formula (Hill Notation):
C27H58NO6P
CAS Number:
70641-51-9
Molecular Weight:
523.73
MDL number:
MFCD00135190
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

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

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. Inhibits protein kinase C from various leukemic cells. Also promotes rapid and selective apoptosis in human leukemic cells. Has strong antitumor and anticancer properties.
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)

Caution

Material may form micelles in aqueous stock solutions, which may affect experimental results.

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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