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Fenretinide

现货
Catalog No.
A3412
合成的维甲酸激动剂
组合的产品项目
规格价格库存 数量
10mM (in 1mL DMSO)
¥ 500.00
现货
10mg
¥ 470.00
现货
50mg
¥ 740.00
现货

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Background

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.

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt391.55
Cas No.65646-68-6
FormulaC26H33NO2
Synonyms4-HPR; (4-Hydroxyphenyl)retinamide
Solubility≥19.6 mg/mL in DMSO, ≥47.8 mg/mL in EtOH with gentle warming, <2.13 mg/mL in H2O
Chemical Name(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
SDFDownload SDF
Canonical SMILESCC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)C
运输条件试用装:蓝冰运输。 其他可选规格:常温运输或根据您的要求用蓝冰运输。
一般建议为了使其更好的溶解,请用37℃加热试管并在超声波水浴中震动片刻。不同厂家不同批次产品溶解度各有差异,仅做参考。若实验所需浓度过大至产品溶解极限,请添加助溶剂助溶或自行调整浓度。

试验操作

细胞实验 [1-3]:

细胞系

T-ALL细胞系,CCRF-CEM白血病细胞,CCRF-CEM和Jurkat细胞,OVCAR-5细胞系

溶解方法

该化合物在DMSO中的溶解度大于19.6 mg/mL。若获取更高浓度的溶液,可在37℃下孵育10分钟,随后在超声波浴中摇匀。-20℃以下可储存数月。

反应条件

>1 μM, 3 days

应用

Fenretinide抑制许多肿瘤细胞的生长,包括小细胞肺癌、恶性造血细胞和乳腺癌细胞。在222和UCI 101卵巢癌细胞系中,Fenretinide的IC50值分别为0.3和0.4 μM。在选择的T-ALL细胞系中,Fenretinide显示出抗肿瘤活性。Fenretinide以剂量和时间依赖的方式抑制CCRF-CEM白血病细胞中的DES活性,导致内源性细胞dhCer含量的伴随增加。在CCRF-CEM和Jurkat细胞中,Fenretinide(3 μM)诱导dhCer积累。Fenretinide(>1 μM)抑制OVCAR-5细胞增殖和活力,在10 μM浓度下产生70-90%的生长抑制。Fenretinide(1 μM)预孵育3天后,显著抑制OVCAR-5侵袭。

动物实验[4,5]:

动物模型

HFD喂养的雄性C57Bl/6小鼠,NOD/SCID小鼠

给药剂量

腹腔注射,10 mg/kg

应用

在HFD喂养的雄性C57Bl/6小鼠中,Fenretinide (10 mg/kg, i.p.)选择性地抑制神经酰胺积聚。Fenretinide改善葡萄糖耐量和胰岛素敏感性。在NOD/SCID小鼠中,向Fenretinide中添加25 mg/kg酮康唑增加了4-HPR血浆水平。

注意事项

由于实验环境的不同,实际溶解度可能与理论值略有不同,请测试室内所有化合物的溶解度。

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.

生物活性

Description Fenretinide是人工合成的维甲酸衍生物。
靶点 RAR          
IC50            

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