Edelfosine | CAS#70641-51-9 | PI-PLC inhibitor

MedKoo Cat#: 341191 | Name: Edelfosine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Edelfosine is a synthetic lysophospholipid analog that selectively inhibits phosphatidylinositol phospholipase C (IC50 = 9.6 μM in fibroblasts and adenocarcinoma cells). Edelfosine acts as an agonist at platelet-activating factor (PAF) receptors. Edelfosine is an antitumor lipid that selectively induces apoptosis in tumor cells, sparing normal cells, and activates the intracellular Fas/CD95 death receptor. Edelfosine also triggers eryptosis and interacts with mitochondrial membranes to increase mitochondrial membrane permeability, leading to dysfunction and apoptosis.

Chemical Structure

Edelfosine

CAS#70641-51-9

Theoretical Analysis

MedKoo Cat#: 341191

Name: Edelfosine

CAS#: 70641-51-9

Chemical Formula: C27H58NO6P

Exact Mass: 523.4002

Molecular Weight: 523.74

Elemental Analysis: C, 61.92; H, 11.16; N, 2.67; O, 18.33; P, 5.91

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450.00	2 Weeks

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Related CAS #

No Data

Synonym

Edelfosine; ET-18-OMe; Edelfosina; ET 18-OCH3; ET-18-O Me; Ro 14-5243; NSC-324368; NSC324368; NSC 324368; NSC-343649; NSC343649; NSC 343649;

IUPAC/Chemical Name

3,5,9-Trioxa-4-phosphaheptacosan-1-aminium, 4-hydroxy-7-methoxy-N,N,N-trimethyl-, hydroxide, inner salt, 4-oxide, (+-)-

InChi Key

MHFRGQHAERHWKZ-UHFFFAOYSA-N

InChi Code

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

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Water	10.5	20.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 523.74 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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PMID: 29514688; PMCID: PMC5842581. 8: Alves ACS, Dias RA, Kagami LP, das Neves GM, Torres FC, Eifler-Lima VL, Carvalho I, de Miranda Silva C, Kawano DF. Beyond the "Lock and Key" Paradigm: Targeting Lipid Rafts to Induce the Selective Apoptosis of Cancer Cells. Curr Med Chem. 2018;25(18):2082-2104. doi: 10.2174/0929867325666180111100601. PMID: 29332565. 9: Jaffrès PA, Gajate C, Bouchet AM, Couthon-Gourvès H, Chantôme A, Potier- Cartereau M, Besson P, Bougnoux P, Mollinedo F, Vandier C. Alkyl ether lipids, ion channels and lipid raft reorganization in cancer therapy. Pharmacol Ther. 2016 Sep;165:114-31. doi: 10.1016/j.pharmthera.2016.06.003. Epub 2016 Jun 8. PMID: 27288726. 10: Gajate C, Mollinedo F. Lipid raft-mediated Fas/CD95 apoptotic signaling in leukemic cells and normal leukocytes and therapeutic implications. J Leukoc Biol. 2015 Nov;98(5):739-59. doi: 10.1189/jlb.2MR0215-055R. Epub 2015 Aug 5. PMID: 26246489. 11: Mollinedo F, Gajate C. Lipid rafts as major platforms for signaling regulation in cancer. Adv Biol Regul. 2015 Jan;57:130-46. doi: 10.1016/j.jbior.2014.10.003. Epub 2014 Oct 27. PMID: 25465296. 12: Gajate C, Mollinedo F. Lipid rafts, endoplasmic reticulum and mitochondria in the antitumor action of the alkylphospholipid analog edelfosine. Anticancer Agents Med Chem. 2014 May;14(4):509-27. doi: 10.2174/1871520614666140309222259. PMID: 24628241. 13: Semini G, Hildmann A, von Haefen C, Danker K. Glycosidated phospholipids - a promising group of anti-tumour lipids. Anticancer Agents Med Chem. 2014 May;14(4):607-17. doi: 10.2174/1871520614666140309222845. PMID: 24628240. 14: Verheij M, Moolenaar WH, Blitterswijk WJ. Combining anti-tumor alkyl- phospholipid analogs and radiotherapy: rationale and clinical outlook. Anticancer Agents Med Chem. 2014 May;14(4):618-28. doi: 10.2174/1871520614666140309224145. PMID: 24628238. 15: Marco C, Ríos-Marco P, Jiménez-López JM, Segovia JL, Carrasco MP. Antitumoral alkylphospholipids alter cell lipid metabolism. Anticancer Agents Med Chem. 2014 May;14(4):545-58. doi: 10.2174/1871520614666140309224707. PMID: 24628237. 16: Dynarowicz-Latka P, Hac-Wydro K. Edelfosine in membrane environment - the Langmuir monolayer studies. Anticancer Agents Med Chem. 2014 May;14(4):499-508. doi: 10.2174/1871520614666140309230722. PMID: 24628234. 17: Van Slambrouck S, Steelant WF. 1-O-octadecyl-2-O-methylglycero-3-phosphocholine (Edelfosine) and cancer cell invasion: a short review. Anticancer Agents Med Chem. 2014 May;14(4):539-44. doi: 10.2174/1871520614666140309231505. PMID: 24628232. 18: van Blitterswijk WJ, Verheij M. Anticancer mechanisms and clinical application of alkylphospholipids. Biochim Biophys Acta. 2013 Mar;1831(3):663-74. doi: 10.1016/j.bbalip.2012.10.008. Epub 2012 Nov 5. PMID: 23137567. 19: Girault A, Haelters JP, Potier-Cartereau M, Chantôme A, Jaffrés PA, Bougnoux P, Joulin V, Vandier C. 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