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

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

MedKoo CAT#: 341191

CAS#: 70641-51-9

Description: 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

Instruction

Theoretical Analysis

MedKoo Cat#: 341191
Name: Edelfosine
CAS#: 70641-51-9
Chemical Formula: C27H58NO6P
Exact Mass: 523.40
Molecular Weight: 523.736
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 310	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Edelfosine; BRN 4358577; BRN-4358577; BRN4358577;

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

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Water	10.5	20.00

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Mollinedo F, Gajate C. Direct Endoplasmic Reticulum Targeting by the Selective Alkylphospholipid Analog and Antitumor Ether Lipid Edelfosine as a Therapeutic Approach in Pancreatic Cancer. Cancers (Basel). 2021 Aug 19;13(16):4173. doi: 10.3390/cancers13164173. PMID: 34439330; PMCID: PMC8394177.

2: Mollinedo F, Gajate C. Mitochondrial Targeting Involving Cholesterol-Rich Lipid Rafts in the Mechanism of Action of the Antitumor Ether Lipid and Alkylphospholipid Analog Edelfosine. Pharmaceutics. 2021 May 20;13(5):763. doi: 10.3390/pharmaceutics13050763. PMID: 34065546; PMCID: PMC8161315.

3: Garbayo E, Pascual-Gil S, Rodríguez-Nogales C, Saludas L, Estella-Hermoso de Mendoza A, Blanco-Prieto MJ. Nanomedicine and drug delivery systems in cancer and regenerative medicine. Wiley Interdiscip Rev Nanomed Nanobiotechnol. 2020 Sep;12(5):e1637. doi: 10.1002/wnan.1637. Epub 2020 Apr 29. PMID: 32351045.

4: van Senten JR, Fan TS, Siderius M, Smit MJ. Viral G protein-coupled receptors as modulators of cancer hallmarks. Pharmacol Res. 2020 Jun;156:104804. doi: 10.1016/j.phrs.2020.104804. Epub 2020 Apr 8. PMID: 32278040.

5: Buechler C, Aslanidis C. Role of lipids in pathophysiology, diagnosis and therapy of hepatocellular carcinoma. Biochim Biophys Acta Mol Cell Biol Lipids. 2020 May;1865(5):158658. doi: 10.1016/j.bbalip.2020.158658. Epub 2020 Feb 10. PMID: 32058031.

6: Zaremberg V, Ganesan S, Mahadeo M. Lipids and Membrane Microdomains: The Glycerolipid and Alkylphosphocholine Class of Cancer Chemotherapeutic Drugs. Handb Exp Pharmacol. 2020;259:261-288. doi: 10.1007/164_2019_222. PMID: 31302758.

7: Messias MCF, Mecatti GC, Priolli DG, de Oliveira Carvalho P. Plasmalogen lipids: functional mechanism and their involvement in gastrointestinal cancer. Lipids Health Dis. 2018 Mar 7;17(1):41. doi: 10.1186/s12944-018-0685-9. 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. Targeting SKCa channels in cancer: potential new therapeutic approaches. Curr Med Chem. 2012;19(5):697-713. doi: 10.2174/092986712798992039. PMID: 22204342.

20: Gajate C, Mollinedo F. Lipid rafts and Fas/CD95 signaling in cancer chemotherapy. Recent Pat Anticancer Drug Discov. 2011 Sep;6(3):274-83. doi: 10.2174/157489211796957766. PMID: 21762074.

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