Piceatannol
(Synonyms: 白皮杉醇; Astringenin; trans-Piceatannol) 目录号 : GN10503
Piceatannol(3,3 '，4,5 ' -反式三羟基二苯乙烯)是天然存在的白藜芦醇羟基化类似物。
Cas No.:10083-24-6
Sample solution is provided at 25 µL, 10mM.
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Piceatannol (3,3′,4,5′-trans-trihydroxystilbene) is a naturally occurring hydroxylated analogue of resveratrol [1]. Piceatannol inhibited mushroom tyrosinase with IC50 value of 1.53 mM [2]. piceatannol is a spleen tyrosine kinase (Syk) inhibitor, it is often used in studies involving Syk kinase-dependent cells [3,4], especially neutrophils [5,6], macrophages [7,8] and smooth muscle cells [9,10].
Piceatannol was used to specifically inhibit Syk, which is an important adaptor of FcγR cross-linking-induced downstream signaling. Application of Piceatannol aborted cyclin D1 expression induced by FcγR cross-linking in murine bone marrow-derived macrophages (BMM) [7]. Pre-incubation of piceatannol (100 nM for 1 h) increased neutrophil adhesion in the presence of E3MPO, reversing the non-adherent phenotype of the cells [5]. piceatannol inhibited Ang II-enhanced rat aortic smooth muscle cells (RASMCs) migration, and inhibited Ang II-stimulated phosphorylation of ERK1/2, p38 MAPK and Hsp27, pretreatment with piceatannol attenuated Ang II-increased sprout outgrowth from aortic rings [9].
Piceatannol (10 or 20 mg/kg/d, 3 weeks, oral) administration significantly decreases solid tumor growth in BALB/c mice injected with 4T1 mammary cancer cells [11]. Piceatannol (20 mg/kg/d, 9 days, oral) inhibits lung metastasis of MAT-Ly-Lu (MLL) cells in nude mice [12].
References:
[1]. Piotrowska H, Kucinska M, Murias M. Biological activity of piceatannol: leaving the shadow of resveratrol[J]. Mutation Research/Reviews in Mutation Research, 2012, 750(1): 60-82.
[2]. Yokozawa T, Kim Y J. Piceatannol inhibits melanogenesis by its antioxidative actions[J]. Biological and Pharmaceutical Bulletin, 2007, 30(11).
[3]. Pavanetto M, Zarpellon A, Borgo C, et al. Regulation of serotonin transport in human platelets by tyrosine kinase Syk[J]. Cellular Physiology and Biochemistry, 2011, 27(2): 139-148.
[4]. Beckmann S, Buro C, Dissous C, et al. The Syk kinase SmTK4 of Schistosoma mansoni is involved in the regulation of spermatogenesis and oogenesis[J]. PLoS Pathogens, 2010, 6(2): e1000769.
[5]. Hayes M J, Cambridge G. An IgM class anti-neutrophil cytoplasm antibody inhibits neutrophil adhesion and apoptosis via a Syk dependent signaling cascade[J]. Molecular immunology, 2004, 41(4): 457-468.
[6]. Ortiz‐Stern A, Rosales C. FcγRIIIB stimulation promotes β1 integrin activation in human neutrophils[J]. Journal of leukocyte biology, 2005, 77(5): 787-799.
[7]. Luo Y, Pollard J W, Casadevall A. Fcγ receptor cross-linking stimulates cell proliferation of macrophages via the ERK pathway[J]. Journal of Biological Chemistry, 2010, 285(6): 4232-4242.
[8]. Gevrey J C, Isaac B M, Cox D. Syk is required for monocyte/macrophage chemotaxis to CX3CL1 (Fractalkine)[J]. The Journal of Immunology, 2005, 175(6): 3737-3745.
[9]. Lau H K F, Ho J. Regulation of plasminogen activator inhibitor‿ secretion by urokinase and tissue plasminogen activator in rat epithelioid‐type smooth muscle cells[J]. British journal of haematology, 2002, 117(1): 151-158.
[10]. Lee H M, Lee C K, Lee S H, et al. p38 mitogen-activated protein kinase contributes to angiotensin II-stimulated migration of rat aortic smooth muscle cells[J]. Journal of pharmacological sciences, 2007, 105(1): 74-81.
[11]. Song H, Jung J I, Cho H J, et al. Inhibition of tumor progression by oral piceatannol in mouse 4T1 mammary cancer is associated with decreased angiogenesis and macrophage infiltration[J]. The Journal of nutritional biochemistry, 2015, 26(11): 1368-1378.
[12]. Kwon G T, Jung J I, Song H R, et al. Piceatannol inhibits migration and invasion of prostate cancer cells: possible mediation by decreased interleukin-6 signaling[J]. The Journal of nutritional biochemistry, 2012, 23(3): 228-238.
| Cell experiment [1]: | |
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Cell lines |
Mouse brain endothelial cell line bEnd.3 |
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Preparation Method |
The bEnd.3 cells were cultured in DMEM containing 10% FBS plus 100 U/mL penicillin and 100 U/mL streptomycin at 37 °C in a humidified atmosphere with 5% CO2. Cells were subcultured every 2-3 days. All the experiments with bEnd.3 cells were performed between passages 5 to 25 for maintaining excellent BBB characteristics in vitro. The bEnd.3 cell impaired model was induced by treating with LPS at two different concentrations and stimulation times (1 µg/mL for 24 h or 10 µg/mL for 1 h) to examine different target proteins modulating inflammatory and antioxidant responses. Piceatannol (10 or 50 µM) was added to the medium for 30 min and then LPS (10 µg/mL) was added in the existing medium containing piceatannol for 1 h. For another set of experiments, cells were pretreated with piceatannol for 4 h before LPS stimulation (1 µg/mL for 24 h) in the existing medium. Piceatannol was dissolved in 1% dimethyl sulfoxide (DMSO), and LPS was dissolved in phosphate-buffered saline (PBS). |
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Reaction Conditions |
10 or 50 µM for 1.5 or 28 hours |
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Applications |
The protein expression of ICAM-1 and VCAM-1 was upregulated by LPS (1 µg/mL) exposure for 24 h, whereas such upregulation was reversed by pretreatment with 50 µM piceatannol for 4 h in bEnd.3 cells |
| Animal experiment [2]: | |
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Animal models |
Four-week-old female BALB/c mice |
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Preparation Method |
After given 2 weeks for adaption, 4T1-luc cells (5×104 cells) suspended in 0.1-ml matrigel/PBS (1:1, v/v) were injected into the inguinal mammary fat pad. One day after injection, the animals were randomly divided into three experimental groups. Piceatannol (10 or 20 mg/kg) in corn oil or corn oil (vehicle) alone was administered to the mice by oral gavage every day for 30 days. |
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Dosage form |
Oral, 10 or 20 mg/kg |
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Applications |
Tumor weights were also significantly lower in the mice administered with Piceatannol than in the control group. At the time of sacrifice, the tumor weights were 0.915±0.037 g, 0.740±0.028 g and 0.668±0.047 g in the 0-mg/kg Piceatannol, 10-mg/kg Piceatannol and 20-mg/kg Piceatannol groups, respectively. |
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References: [1]: Zhou Y, Khan H, Hoi M P M, et al. Piceatannol Protects Brain Endothelial Cell Line (bEnd. 3) against Lipopolysaccharide-Induced Inflammation and Oxidative Stress[J]. Molecules, 2022, 27(4): 1206. |
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| Cas No. | 10083-24-6 | SDF | |
| 别名 | 白皮杉醇; Astringenin; trans-Piceatannol | ||
| 化学名 | 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol | ||
| Canonical SMILES | C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O | ||
| 分子式 | C14H12O4 | 分子量 | 244.24 |
| 溶解度 | ≥ 12.2mg/mL in DMSO | 储存条件 | Store at 2-8°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℃，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 | 4.0943 mL | 20.4717 mL | 40.9433 mL |
| 5 mM | 0.8189 mL | 4.0943 mL | 8.1887 mL |
| 10 mM | 0.4094 mL | 2.0472 mL | 4.0943 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: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet