GLPBio

(R)-Edelfosine

Catalog No.: GC16687Purity:>99.00%Synonyms: 2-O-methyl PAF C-18
Edelfosine ((R) -ET-18-OCH3) هو نظير لدهن الأثير مع نشاط مضاد لفيروس نقص المناعة البشرية ومضاد الأورام.

المنتجات مخصصة للاستخدام البحثي فقط، وليست للاستخدام البشري. نحن لا نبيع للمرضى.


(R)-Edelfosine
Cas No.: 77286-66-9
1mgIn Stock
$60.00
1
5mgIn Stock
$178.00
1
10mgIn Stock
$294.00
1

المراجع (Citations)

لا تتوفر حاليًا مراجع لهذا المنتج. فيما يلي مجموعة مختارة من المنشورات التي تستشهد بمنتجات GlpBio.
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    610, 366–372 (2022)
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    Cell
    187(9):2288-2304 (2024)
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    183(7):1867-1883 (2020)
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الوصف (Description)

(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.

البروتوكول (Protocol)

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:
[1] Dakir EH, Gajate C, Mollinedo F. Antitumor activity of alkylphospholipid edelfosine in prostate cancer models and endoplasmic reticulum targeting. Biomed Pharmacother. 2023 Nov;167:115436.
[2] 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.

وثائق المنتج (Product Documents)

Purity:>99.00%Appearance:A solid

الخصائص الكيميائية (Chemical Properties)

رقم CAS
77286-66-9
المرادفات
2-O-methyl PAF C-18
الاسم الكيميائي
(S)-2-methoxy-3-(octadecyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
SMILES
[O-][P@@](OCC[N+](C)(C)C)(OC[C@H](COCCCCCCCCCCCCCCCCCC)OC)=O
الصيغة الجزيئية
C27H58NO6P
الوزن الجزيئي
523.73
الذوبانية
PBS pH 7.2: 1 mg/ml
التخزين
Store at -20°C
إرشادات عامة
اختر مذيبًا مناسبًا وفقًا لبيانات ذوبانية المنتج. بعد التحضير، قسّم المحلول المخزون إلى أجزاء لتجنب دورات التجميد والذوبان المتكررة.
استخدم المحاليل المخزونة خلال 6 أشهر عند حفظها في -80°C، أو خلال شهر واحد عند حفظها في -20°C.
لتحسين الذوبانية، سخّن الأنبوب إلى 37°C وعرّضه للموجات فوق الصوتية لمدة مناسبة.
شروط الشحن
تُشحن عينات التقييم مع عبوات تبريد. وتُشحن الأحجام الأخرى المتاحة في درجة حرارة الغرفة، أو مع عبوات تبريد عند الطلب.

الحاسبات (Calculators)المولارية / التخفيف / الوزن الجزيئي / تحويل الوحدات / تركيبة داخل الجسم الحي / الذوبانية

g/mol

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