(R)-Edelfosine (Synonyms: 2-O-methyl PAF C-18) |
Catalog No.GC16687
One-Click Copy Product Info
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(R)-Edelfosine is a synthetic lipid agent belonging to a class of compounds with antitumor and antiparasitic activities. (R)-Edelfosine can induce apoptosis-like cell death in tumor cells by targeting FOF1-ATP synthase on mitochondria and lipid rafts.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 77286-66-9
Sample solution is provided at 25 µL, 10mM.
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(R)-Edelfosine is a synthetic lipid agent belonging to a class of compounds with antitumor and antiparasitic activities[1]. (R)-Edelfosine can induce apoptosis-like cell death in tumor cells by targeting FOF1-ATP synthase on mitochondria and lipid rafts[2]. (R)-Edelfosine also exhibits antileishmanial and antischistosomal activities[3]. (R)-Edelfosine acts as a novel HIV-1 latency-reversing agent[4].
In vitro, treatment of prostate cancer cells (LNCaP, PC3, and DU145) with (R)-Edelfosine (5–30μM) for 24–72 hours leads to accumulation in the endoplasmic reticulum, inducing endoplasmic reticulum stress, significantly promoting caspase-3 activation and PARP cleavage, and triggering apoptosis[5]. Treatment of non-small cell lung cancer cells (NCI-H157, NCI-H520, NCI-H522) with (R)-Edelfosine (2.6–100μM) for 24–72 hours inhibits phospholipase C-B1 activity, induces G2/M phase arrest and c-Jun N-terminal kinase activation, and significantly promotes apoptosis and necrosis[6].
In vivo, daily oral administration of (R)-Edelfosine (30mg/kg) starting from day 5 after tail vein injection of 435-Lung-eGFP-CMV/Luc metastatic cancer cells until week 12 in nude mice significantly inhibits metastatic tumor colonization in the lungs and brain, while prolonging the survival of tumor-bearing mice[7]. Oral administration of (R)-Edelfosine (5–20mg/kg) three times per week in an orthotopic LNCaP cell xenograft mouse model, combined with androgen deprivation (bilateral orchiectomy), significantly suppresses tumor volume growth[8].
References:
[1] Teixeira SF, Rodrigues CP, Costa CJS, et al. Edelfosine: An Antitumor Drug Prototype. Anticancer Agents Med Chem. 2018;18(6):865-874.
[2] 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.
[3] Tanzifi A, Khoshi A, Emami S, et al. The effect of edelfosine on GRA1 and MIC3 expressions in acute toxoplasmosis. Parasitol Res. 2020 Apr;119(4):1371-1380.
[4] Rai M, Rawat K, Muhammadi MK, et al. Edelfosine reactivates latent HIV-1 reservoirs in myeloid cells through activation of NF-κB and AP1 pathway. Virology. 2022 Sep;574:57-64.
[5] Dakir EH, Gajate C, Mollinedo F, et al. Antitumor activity of alkylphospholipid edelfosine in prostate cancer models and endoplasmic reticulum targeting. Biomed Pharmacother. 2023 Nov;167:115436.
[6] Shafer SH, Williams CL, et al. Non-small and small cell lung carcinoma cell lines exhibit cell type-specific sensitivity to edelfosine-induced cell death and different cell line-specific responses to edelfosine treatment. Int J Oncol. 2003 Aug;23(2):389-400.
[7] Alonso-Pérez V, Hernández V, Calzado MA, et al. Suppression of metastatic organ colonization and antiangiogenic activity of the orally bioavailable lipid raft-targeted alkylphospholipid edelfosine. Biomed Pharmacother. 2024 Feb;171:116149.
[8] Udayakumar TS, Stoyanova R, Shareef MM, et al. Edelfosine Promotes Apoptosis in Androgen-Deprived Prostate Tumors by Increasing ATF3 and Inhibiting Androgen Receptor Activity. Mol Cancer Ther. 2016 Jun;15(6):1353-63.
| Cell experiment [1]: | |
Cell lines | LNCaP, PC3, and DU145 cells (human prostate cancer cell lines with distinct androgen dependency, and differing PTEN and p53 status) |
Preparation Method | Cells were grown in RPMI-1640 medium supplemented with 10% heat-inactivated fetal bovine serum (FBS), 100U/ml penicillin, 100μg/ml streptomycin, and 2mM L-glutamine at 37°C in a humidified atmosphere containing 5% CO₂. Exponentially growing cells were treated with (R)-Edelfosine (5-30μM; 24-72 hours). |
Reaction Conditions | 5-30μM; 24-72 hours |
Applications | (R)-Edelfosine was the most potent alkylphospholipid analog in inducing apoptosis. (R)-Edelfosine accumulated in the endoplasmic reticulum (ER) of prostate cancer cells, leading to ER stress and cell death. Treatment induced a G2/M cell cycle arrest prior to apoptosis onset. (R)-Edelfosine also triggered a potent autophagic response in LNCaP and PC3 cells, and inhibition of autophagy potentiated its pro-apoptotic activity. |
| Animal experiment [2]: | |
Animal models | Male athymic nude mice (orthotopic LNCaP tumor model) |
Preparation Method | LNCaP cells (5 x 10⁵) were implanted into the dorsal prostate of mice. Two weeks post-implantation, mice with serum PSA levels of 3.0-8.0ng/mL were treated orally by gavage. Androgen deprivation (AD) was achieved via bilateral orchiectomy 3 days prior to (R)-Edelfosine (5, 10, and 20mg/kg; orally) treatment in the AD groups. |
Dosage form | 5, 10, and 20mg/kg; orally |
Applications | (R)-Edelfosine combined with AD resulted in a significant decrease in tumor volume and serum PSA levels compared to (R)-Edelfosine alone. The combination treatment showed the greatest antitumor effect, with a more than 7-fold decrease in tumor volume and PSA levels. |
References: | |
| Cas No. | 77286-66-9 | SDF | |
| Synonyms | 2-O-methyl PAF C-18 | ||
| Chemical Name | (S)-2-methoxy-3-(octadecyloxy)propyl (2-(trimethylammonio)ethyl) phosphate | ||
| Canonical SMILES | [O-][P@@](OCC[N+](C)(C)C)(OC[C@H](COCCCCCCCCCCCCCCCCCC)OC)=O | ||
| Formula | C27H58NO6P | M.Wt | 523.73 |
| Solubility | PBS pH 7.2: 1 mg/ml | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.9094 mL | 9.5469 mL | 19.0938 mL |
| 5 mM | 381.9 μL | 1.9094 mL | 3.8188 mL |
| 10 mM | 190.9 μL | 954.7 μL | 1.9094 mL |
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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
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- Purity: >99.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 16 reference(s) in Google Scholar.)