Piceatannol

Catalog No.S3026

Piceatannol Chemical Structure

Molecular Weight(MW): 244.24

Piceatannol, a natural stilbene, is a selective Syk inhibitor and ~10-fold selectivity versus Lyn.

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2 Customer Reviews

  • Influence of piceatannol and resveratrol on hydrogen peroxide production by human subcutaneous fat tissue. H202 release was monitored on a 30-min period without any added agent, except the chromogenic mixture (basal), or with NADPH oxidase inhibitor (apocynin 10 μM, shaded column), each stilbene at 1 mM, or MAO and SSAO inhibitors (pargyline plus semicarbazide at 1 mM: parg + semi, dotted column). Each column is the mean ± SEM of 16 homogenates from obese patients. Different from basal hydrogen peroxide production at: **P < 0.01.

    Chem Biol Interact, 2016, 258:115-25. . Piceatannol purchased from Selleck.

    Change of protein and mRNA with or without the pretreatment of Syk inhibitors. After pretreated with PRT062607 and Piceatannol for 30 min before A. fumigatus hyphae stimulation, activation of Syk was inhibited by 1 μM PRT062607 (p < 0.05), 2 μM PRT062607 (p < 0.01), 5 μM Piceatannol (p < 0.05), 10 μM Piceatannol (p < 0.01) a compared with untreated cells. mRNA expression of IL-1β, IL-6, IL-8 and CXCL1 induced by A. fumigatus hyphae were significantly suppressed b. mRNA expression of IL-1β, IL-6, IL-8, CXCL1 downregulated significantly by 1 μM PRT062607, 2 μM PRT062607, 5 μM Piceatannol, 10 μM Piceatannol. **means p < 0.01, *p < 0.05.

    BMC Ophthalmol, 2014, 15:56.. Piceatannol purchased from Selleck.

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Biological Activity

Description Piceatannol, a natural stilbene, is a selective Syk inhibitor and ~10-fold selectivity versus Lyn.
Targets
Syk [1]
(Cell-free assay)
Lyn [1]
(Cell-free assay)
cAK [2]
(Cell-free assay)
PKC [2]
(Cell-free assay)
MLCK [2]
(Cell-free assay)
3 μM 8 μM 12 μM
In vitro

Piceatannol displays ~10-fold selectivity for Syk over Lyn. Piceatannol treatment in RBL-2H3 cells strongly inhibits the antigen-stimulated phosphorylation of Syk and of most other cellular proteins but not the receptor β or γ subunit, in a dose-dependent manner. Piceatannol is also a potent inhibitor of histamine release in mast cells. Selective inhibition of Syk by Piceatannol blocks receptor-mediated down-stream cellular responses in mast cells including prevention of 1,4,5-IP3 synthesis, secretion and membrane ruffling and spreading. [1] Piceatannol also potently inhibits PKA, PKC, MLCK, and CDPK with IC50 of 3 μM, 8 μM, 12 μM, and 19 μM, respectively. [2] Piceatannol selectively prevents the IFNα-induced tyrosine phosphorylation of STAT3 and -5 but not STAT1 and -2, paralleled by the loss of Jak1 and IFNAR1 tyrosine phosphorylation but not Tyk2 and IFNAR2. [3] Piceatannol potently induces apoptotic cell death in BJAB Burkitt-like lymphoma cells with ED50 of 25 μM, through the activation of caspase-3 and mitochondrial permeability transition independent of the CD95/Fas signaling pathway. [4] Piceatannol inhibits NF-κB activation induced by TNF, H2O2, PMA, LPS, okadaic acid, and ceramide. Piceatannol suppresses the expression of TNF-induced NF-κB-dependent reporter gene and of matrix metalloprotease-9, cyclooxygenase-2, and cyclin D1 independent of Syk kinase, by blocking TNF-induced IκBα phosphorylation, p65 phosphorylation, p65 nuclear translocation, and IκBα kinase activation. [5] Piceatannol directly binds with PI3K in an ATP-competitive manner, and suppresses PI3K activity with anti-atherosclerotic effects more effectively than resveratrol. [8] Piceatannol inhibits androgen-dependent (AD) and androgen-independent (AI) CaP cell proliferation, which is accompanied by reduced expression of mTOR and its key effectors AKT and eIF4EBP-1. [10]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
human lung mast cells MkXJSpVv[3Srb36gZZN{[Xl? NUDLTIVTUW6qaXLpeIlwdiCxZjDTXWshcW5iaIXtZY4hdHWwZzDtZZN1KGOnbHzzJIF{e2W|c3XkJIF{KHKnZIXjeIlwdiCrbjDhcpRqNUmpRT3zeIlufWyjdHXkJIhqe3SjbXnu[UBz\WynYYPlMEBGSzVyPUK1JO69VQ>? M{PkNVIzOjV5MkGz
human A2780 cells MXzQdo9tcW[ncnH0bY9vKGG|c3H5 NWHvR5FnOiCmYYnz NEfnfHpCdnSrcILvcIln\XKjdHn2[UBi[3Srdnn0fUBi\2GrboP0JIh2dWGwIFGyO|gxKGOnbHzzJIFnfGW{IEKg[IF6eyCkeTDBcIFu[XJiQnz1[UBie3OjeTygTWM2OD12MTFOwG0> NEX2e4kzPDJ|OUO5NC=>
mouse 3T3L1 cells NEeyO|hHfW6ldHnvckBie3OjeR?= M1j4OFExKHSxIEWwJO69VQ>? NHvWTYY1QCCq MmjCVoVlfWO2aX;uJIlvKHS{aXfsfYNmemmmZTDs[ZZmdCCrbjDtc5V{\SB|VEPMNUBk\WyuczDheEAyOCC2bzC1NEB2VSCjZoTldkA1QCCqcoO= MV2yNlc3PTh7Nh?=

... Click to View More Cell Line Experimental Data

In vivo Oral administration of Piceatannol induces a remarkable amelioration of the disruption of the colonic architecture, a significant reduction in colonic myeloperoxidase (MPO) activity, and a decrease in production of inflammatory mediators such as nitric oxide (NO), prostaglandin (PG) E2, and pro-inflammatory cytokines in BALB/c mice with dextran sulfate sodium (DSS)-induced colitis. [7] Piceatannol treatment inhibits the rises in blood glucose levels at early stages and improves the impaired glucose tolerance at late stages in type 2 diabetic model db/db mice. [9]

Protocol

Kinase Assay:

[1]

+ Expand

In Vitro Protein-tyrosine Kinase Assays:

Recombinant Syk is expressed in baculovirus-infected St9 cells. Assays of recombinant Syk activity are carried out using angiotensin I peptide as substrate. The enzyme activities of recombinant Syk are measured by phosphorylation of angiotensin I peptide in the presence of various concentrations of Piceatannol.
Cell Research:

[10]

+ Expand
  • Cell lines: LNCaP, DU145, and PC-3
  • Concentrations: Dissolved in DMSO, final concentrations ~50 μM
  • Incubation Time: 72 hours and 1 week
  • Method:

    Cells are exposed to increasing concentrations of Piceatannol. For the determination of cell proliferation, cells are assayed at 72 hours by trypan blue exclusion using a hemocytometer. After 1 week, colonies are stained with 1.25% crystal violet and quantified by measuring the absorbance at 595 nm.


    (Only for Reference)
Animal Research:

[7]

+ Expand
  • Animal Models: Female BALB/c mice with dextran sulfate sodium (DSS)-induced colitis
  • Formulation: Dissolved in DMSO, and diluted in corn oil
  • Dosages: ~10 mg/kg/day
  • Administration: Orally
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 48 mg/mL (196.52 mM)
Ethanol 48 mg/mL (196.52 mM)
Water Insoluble
In vivo Add solvents to the product individually and in order(Data is from Selleck tests instead of citations):
1% DMSO+30% polyethylene glycol+1% Tween 80
For best results, use promptly after mixing.
30 mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 244.24
Formula

C14H12O4

CAS No. 10083-24-6
Storage powder
in solvent
Synonyms N/A

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Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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Syk Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID