Fenretinide
(Synonyms: 芬维A胺; 4-HPR) 目录号 : GC17143
A synthetic retinoic acid derivative
Cas No.:65646-68-6
Sample solution is provided at 25 µL, 10mM.
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Fenretinide(4HPR) is an inhibitor of Focal adhesion kinase (FAK) [1].
Fenretinideis a vitamin A analogue, it has been shown toinhibit the growth of many tumor cells, including small-cell lung cancer, malignant hemopoietic cells, and breast cancer cells. Fenretinide may also protectwomen against the development of ovarian cancer. The effect of Fenretinide on several gynecologic cancer cell lines shows the IC50 values of Fenretinide are only 0.3 and 0.4μM in two ovarian cancer cell lines(222and UCI 101) and are from 1 to 10μM in other ovarian cancer cell lines and cervical, endometrial cancer cell lines [2].
Fenretinide has also been shown to induce apoptosis inhuman prostate carcinoma cells (HPC).The IC50s of Fenretinide in LNCaP, DU145, and PC-3 are 0.9±0.16μM, 4.4±0.45μM and 3.0±1.0μM,respectively.Fenretinide induces this apoptosis through increasingROS and increasing enzymatic labeling of DNA breaks and formation of a DNA ladder. It is also reported that Fenretinide can impair prostate cancer cell migration and invasion by interfering with FAK/AKT/GSK3β pathway and β-catenin stability [1, 3].
References:
[1] Roberto Benelli, Stefano Monteghirfo, Roberta Venè, Francesca Tosettiand Nicoletta Ferrari.The chemopreventive retinoid 4HPR impairs prostate cancer cell migration and invasion by interfering with FAK/AKT/GSK3β pathway andβ-catenin stability. Molecular Cancer.2010, 9:142-154.
[2] Anita L. Sabichi, Denver T. Hendricks, Mary A. Bober, Michael J. Birrer. Retinoic acid receptorβexpression and growthinhibition of gynecologic cancer cells by thesynthetic retinoidn-(4-hydroxyphenyl) retinamide. Journal of the National Cancer Institute. 1998, 90(8): 597-605.
[3] Shi-Yong Sun, Ping Yue, and Reuben Lotan. Induction of apoptosis by n-(4-hydroxyphenyl)retinamide andits association with reactive oxygen species, nuclearretinoic acid receptors, and apoptosis-related genes in human prostate carcinoma cells.Molecular Pharmacology. 1999, 55:403–410.
| Cell experiment [1-3]: | |
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Cell lines |
T-ALL cell lines, CCRF-CEM leukemia cells, CCRF-CEM and Jurkat cell, OVCAR-5 cell |
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Preparation method |
The solubility of this compound in DMSO is > 19.6 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
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Reacting condition |
>1 μM, 3 days |
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Applications |
Fenretinide inhibited the growth of many tumor cells, including small-cell lung cancer, malignant hemopoietic cells, and breast cancer cells. The IC50 values of Fenretinide were 0.3 and 0.4 μM in 222 and UCI 101 ovarian cancer cell lines. Fenretinide showed antitumor activity in selected T-ALL cell lines. Fenretinide inhibited DES activity in CCRF-CEM leukemia cells in a dose and time dependent manner, leading to a concomitant increase of the endogenous cellular dhCer content. Fenretinide (3 μM) induced dhCer accumulation in both CCRF-CEM and Jurkat cells. Fenretinide (> 1 μM) inhibited OVCAR-5 cell proliferation and viability, with 70-90% growth inhibition at 10 μM. Fenretinide (1 μM) significantly inhibited OVCAR-5 invasion after 3 days preincubation. |
| Animal experiment [4,5]: | |
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Animal models |
HFD-fed male C57Bl/6 mice, NOD/SCID mice |
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Dosage form |
Intraperitoneal injection, 10 mg/kg |
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Application |
Fenretinide (10 mg/kg, i.p.) selectively inhibited ceramide accumulation HFD-fed male C57Bl/6 mice. Fenretinide treatment improved glucose tolerance and insulin sensitivity. Addition of 25 mg/kg ketoconazole to Fenretinide in NOD/SCID mice increased 4-HPR plasma levels. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Apraiz, Aintzane., et al. Dihydroceramide accumulation and reactive oxygen species are distinct and nonessential events in 4-HPR-mediated leukemia cell death. Biochemistry and Cell Biology (2012), 90(2), 209-223. [2]. Golubkov V, et al. Action of fenretinide (4-HPR) on ovarian cancer and endothelial cells. Anticancer Res. 2005 Jan-Feb;25(1A):249-53. [3]. Anita L. Sabichi, Denver T. Hendricks, Mary A. Bober, Michael J. Birrer. Retinoic acid receptorβexpression and growthinhibition of gynecologic cancer cells by thesynthetic retinoidn-(4-hydroxyphenyl) retinamide. Journal of the National Cancer Institute. 1998, 90(8): 597-605. [4]. Bikman, Benjamin T., et al. Fenretinide Prevents Lipid-induced Insulin Resistance by Blocking Ceramide Biosynthesis. Journal of Biological Chemistry (2012), 287(21), 17426-17437. [5]. Cooper JP, et al. Fenretinide metabolism in humans and mice: utilizing pharmacological modulation of its metabolic pathway to increase systemic exposure. Br J Pharmacol. 2011 Jul;163(6):1263-75. |
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| Cas No. | 65646-68-6 | SDF | |
| 别名 | 芬维A胺; 4-HPR | ||
| 化学名 | (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide | ||
| Canonical SMILES | CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)C | ||
| 分子式 | C26H33NO2 | 分子量 | 391.55 |
| 溶解度 | ≥ 19.6 mg/mL in DMSO, ≥ 47.8 mg/mL in EtOH with gentle warming | 储存条件 | Store at -20°C, filled inert atmosphere |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.554 mL | 12.7698 mL | 25.5395 mL |
| 5 mM | 0.5108 mL | 2.554 mL | 5.1079 mL |
| 10 mM | 0.2554 mL | 1.277 mL | 2.554 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet