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SML0332

Sigma-Aldrich

Edelfosine

≥95% (HPLC)

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

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About This Item

Empirical Formula (Hill Notation):
C27H58NO6P
CAS Number:
70641-51-9
Molecular Weight:
523.73
MDL number:
MFCD00135190
UNSPSC Code:
12352200
PubChem Substance ID:
329825337
NACRES:
NA.77

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

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 Code

11 - Combustible Solids

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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Edelfosine Induced Suicidal Death of Human Erythrocytes
Briglia M, et al.
Cellular Physiology and Biochemistry, 37(6), 2221-2230 (2015)
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)
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
TUFT1 interacts with RABGAP1 and regulates mTORC1 signaling.
Kawasaki N, et al.
Cell discovery, 4(1), 1-1 (2018)
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
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