Silvestrol

目录号: GC11455纯度: >98.00%同义词: (1R,2R,3S,3AR,8BS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-二羟基乙基]-3-甲氧基-1,4-二氧己环-2-基]氧基]-2,3,3A,8B-四氢-1,8B-二羟基-8-甲氧基-3A-(4-甲氧基苯基)-3-苯基-1H-环戊烯并[B]苯并呋喃-2-羧酸甲酯,(-)-Silvestrol
Silvestrol 是一种真核翻译起始因子 4A (eIF4A) 抑制剂,从 Agave americana Linn 中分离出来。Silvestrol 诱导自噬和半胱天冬酶介导的细胞凋亡。

Silvestrol
Cas No.: 697235-38-4
规格价格库存数量操作
1mg¥8,910.00现货
1
2mg¥14,850.00现货
1
10mM (in 1mL DMSO)¥53,469.00现货
1

文献被引

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产品描述 Description

Silvestrol inhibited protein synthesis in MDA-MB-231 breast and PC-3 prostate cancer cell lines with IC50 ~60 nM following a 1 h exposure) [1]. Silvestrol inhibited cell growth with an IC50 of 12.5-86 nM in four different HCC cell lines [3].
Silvestrol, a member of flavagline family of natural products from the genus of Aglaia exhibiting anti-cancer activity in vitro and in vivo and inhibiting translation initiation, was shown to be capable of modulating chemosensitivity in a mechanism-based mouse model.
Preclinical study: A previous study demonstrated that silvestrol showed antileukemia activity at nanomolar concentrations in both FLT3-wt overexpressing (THP-1) and FLT3-ITD (MV4-11) expressing AML cell lines (IC50 = 3.8 and 2.7 nM, respectively) and patients' primary blasts [IC50 = ~12 nM (FLT3-wt) and ~5 nM (FLT3-ITD)]. Moreover, silvestrol was observed to efficiently inhibite FLT3 translation resulting in a decrese of FLT3 protein expression by 80–90%. Animal study indicated that the median survival of silvestrol-treated mice significantly increased (silvestrol-treated vs vehicle-treated = 63 vs 29 days postengraftment) [2]. Another study showed that silvestrol could increase the activities of apoptosis and caspase 3/7. In vivo, the antitumor effect was found with 0.4 mg/kg silvestrol, and the survival of tumor-bearing mice was improved with a median survival time of 42 and 28 days in the silvestrol and control groups, respectively [3].
Clinical study: Currently, there is no clinical data about the anti-cancer efficacy of silvestrol. A grant application proposeed to pursue a Phase I clinical trial to assess the safety, maximum tolerated dose, pharmacokinetic and pharmacodynamic properties, and preliminary efficacy of silvestrol in patients with relapsed, refractory Chronic lymphocytic leukemia (Pre-Clinical and Clinical Development of Silvestrol in Chronic Lymphocytic).
References:
[1] Cencic R, Carrier M, Galicia-Vázquez G, Bordeleau ME, Sukarieh R, Bourdeau A, Brem B, Teodoro JG, Greger H, Tremblay ML, Porco JA Jr, Pelletier J Antitumor activity and mechanism of action of the cyclopenta[b]benzofuran, silvestrol. PLoS One. 2009;4(4):e5223. doi: 10.1371/journal.pone.0005223.
[2] Alachkar H, Santhanam R, Harb JG, Lucas DM, Oaks JJ, Hickey CJ, Pan L, Kinghorn AD, Caligiuri MA, Perrotti D, Byrd JC, Garzon R, Grever MR, Marcucci G. Silvestrol exhibits significant in vivo and in vitro antileukemic activities and inhibits FLT3 and miR-155 expressions in acute myeloid leukemia. J Hematol Oncol. 2013;6:21. doi: 10.1186/1756-8722-6-21.
[3] Kogure T, Kinghorn AD, Yan I, Bolon B, Lucas DM, Grever MR, Patel T. Therapeutic potential of the translation inhibitor silvestrol in hepatocellular cancer. PLoS One. 2013;8(9):e76136. doi: 10.1371/journal.pone.0076136.

实验参考方法 Experimental Reference Method

Cell experiment [1]:

Cell lines

Human HCC cells

Preparation method

This compound is soluble in DMSO. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months.

Reacting condition

0 ~ 200 nM; 72 hrs

Applications

Silvestrol potently inhibited human HCC cell growth in a concentration-dependent manner, with an IC50 value of 23.9 nM in PLC/PRF-5 cells, 12.5 nM in Hep-3B cells, 14.6 nM in Huh-7 cells and 86 nM in HepG2 cells.

Animal experiment [1]:

Animal models

Nude mice bearing human HCC xenografts

Dosage form

0.4 or 1 mg/kg; i.p.; 5 days/week, for 4 weeks

Applications

In nude mice bearing human HCC xenografts, a therapeutic response was observed in 36.4% of mice receiving 1 mg/kg Silvestrol and in 20% of mice receiving 0.4 mg/kg Silvestrol. At both doses, Silvestrol significantly increased the survival.

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.

References:

[1]. Kogure T, Kinghorn AD, Yan I, Bolon B, Lucas DM, Grever MR, Patel T. Therapeutic potential of the translation inhibitor silvestrol in hepatocellular cancer. PLoS One. 2013;8(9):e76136. doi: 10.1371/journal.pone.0076136.

产品文档 Product Documents

Purity:>98.00%

化学性质Chemical Properties

CAS 号
697235-38-4
同义词
(1R,2R,3S,3AR,8BS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-二羟基乙基]-3-甲氧基-1,4-二氧己环-2-基]氧基]-2,3,3A,8B-四氢-1,8B-二羟基-8-甲氧基-3A-(4-甲氧基苯基)-3-苯基-1H-环戊烯并[B]苯并呋喃-2-羧酸甲酯,(-)-Silvestrol
化学名
methyl (1R,2R,3S,3aR,8bS)-6-[[(3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
SMILES
COC1C(OC(CO1)C(CO)O)OC2=CC(=C3C(=C2)OC4(C3(C(C(C4C5=CC=CC=C5)C(=O)OC)O)O)C6=CC=C(C=C6)OC)OC
分子式
C34H38O13
分子量
654.66 g/mol
溶解性
Soluble in DMSO
保存条件
Store at -20°C
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°C,然后在超声波浴中震荡一段时间。
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。

计算工具摩尔浓度 / 稀释 / 分子量 / 单位换算 / 体内配方 / 溶解度

g/mol