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341207

ET-18-OCH₃

Name: ET-18-OCH<SUB>3</SUB>
Brand: MM

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

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₅₈NO₆P

CAS Number:

70641-51-9

Molecular Weight:

523.73

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00135190

Assay:

≥95% (TLC)

Form:

solid

Storage condition:

OK to freeze

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Properties

Quality Segment

100

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

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. 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)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c