341207

ET-18-OCH₃

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

• 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

Properties

• 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

Description

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable