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SML0332

Sigma-Aldrich

Edelfosine

≥95% (HPLC)

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Synonym(s):
1-Octadecyl-2-methylglycero-3-phosphorylcholine, 4-Hydroxy-7-methoxy-N,N,N-trimethyl-3,5,9-Trioxa-4-phosphaheptacosan-1-aminium 4-oxide, ALP, ET 18-OCH3, ET-18-OMe, NSC 324368, NSC 343649, Racemic 1-O-octadecyl-2-O-methylglycero-3-phosphocholine, Ro 14-5243
Empirical Formula (Hill Notation):
C27H58NO6P
CAS Number:
Molecular Weight:
523.73
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

H2O: 15 mg/mL (clear solution)

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCCCCOCC(COP([O-])(=O)OCC[N+](C)(C)C)OC

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

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This Item
G1046P3017341207
Edelfosine ≥95% (HPLC)

SML0332

Edelfosine

[6]-Gingerol ≥98% (HPLC)

G1046

[6]-Gingerol

ET-18-OCH3 A cell-permeable and reversible cytotoxic agent that shows selective cytocidal activity against neoplastic cells and virally transformed cells.

341207

ET-18-OCH3

assay

≥95% (HPLC)

assay

≥98% (HPLC)

assay

≥95.5% (GC), ≥98% (TLC)

assay

≥95% (TLC)

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

H2O: 15 mg/mL (clear solution)

solubility

methanol: 1 mg/mL, clear, colorless

solubility

-

solubility

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

color

white to beige

color

-

color

-

color

white

General description

Edelfosine has anti-inflammatory, anti-autoimmune, antiparasitic and anti-viral properties. It stimulates eryptosis by cell shrinkage and cell membrane scrambling.

Application

Edelfosine has been used to treat human lung carcinoma A549 cells and study its effects on tuftelin 1 (TUFT1) expression. It is also used to evaluate the cell growth of MCF-7/M cells.

Biochem/physiol Actions

Edelfosine is a synthetic alkyl-lisophospholipid with anti-tumor activity. The compound induces apoptosis in a variety of cancer cells. Edelfosine accumulates in the cell membrane, where it alters lipid composition and induces the co-clustering of lipid rafts and Fas/CD95 death receptor.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Joo Hee Choi et al.
Colloids and surfaces. B, Biointerfaces, 181, 879-889 (2019-08-07)
In this study, a double network hydrogel of a natural polysaccharide gellan gum (GG) hydrogel and a synthetic hydrogel poloxamer-heparin (PoH) hydrogel (PoH/GG DNH) is introduced to complement disadvantages of each hydrogel and improve the microenvironment for cell delivery. The
Edelfosine Induced Suicidal Death of Human Erythrocytes
Briglia M, et al.
Cellular Physiology and Biochemistry, 37(6), 2221-2230 (2015)
Monica Rapino et al.
Nanomaterials (Basel, Switzerland), 9(7) (2019-06-30)
Dental pulp stem cells (DPSCs) represent a population of stem cells which could be useful in oral and maxillofacial reconstruction. They are part of the periendothelial niche, where their crosstalk with endothelial cells is crucial in the cellular response to
The phenomenon of acquired resistance to metformin in breast cancer cells: The interaction of growth pathways and estrogen receptor signaling
Scherbakov AM, et al.
IUBMB Life, 68(4), 281-292 (2016)
TUFT1 interacts with RABGAP1 and regulates mTORC1 signaling.
Kawasaki N, et al.
Cell discovery, 4(1), 1-1 (2018)

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