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    Piceatannol (Astringenin; NSC-622471; trans-Piceatannol)
    Piceatannol (Astringenin; NSC-622471; trans-Piceatannol)

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    InvivoChem Cat #: V0654
    CAS #: 10083-24-6Purity ≥98%

    Description: Piceatannol (also known as Astringenin; NSC-622471; trans-Piceatannol), a naturally occuring stilbene, is a potent and selective Syk inhibitor and shows ~10-fold selectivity for Srk over Lyn. It has anti-inflammatory, immunomodulatory and antiproliferative activities. Piceatannol  demonstrated high in vivo anti-inflammatory activity in female BALB/c mice with dextran sulfate sodium (DSS)-induced colitis. It inhibits p56lck and syk protein tyrosine kinases and inhibits TNF-induced NF-κB activation and gene expression. Synthesis results from conversion of resveratrol by cytochrome P450 1B1. 

    References: J Biol Chem. 1994 Nov 25;269(47):29697-703.; Int Immunopharmacol. 2008 Dec 10;8(12):1695-702.

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    Molecular Weight (MW)244.24
    FormulaC14H12O4
    CAS No.10083-24-6
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 48 mg/mL (196.5 mM)
    Water: <1 mg/mL
    Ethanol: <48 mg/mL (196.5 mM)
    Solubility (In vivo)1% DMSO+30% polyethylene glycol+1% Tween 80: 30 mg/mL
    Synonyms

    Synonym: NSC 622471; NSC-622471; Piceatannol; NSC622471.

    Chemical Name: (E)-4-[2-(3,5Dihydroxyphenyl)ethenyl]1,2-benzenediol, 3,3′,4,5′-Tetrahydroxy-trans-stilbene

    InChi Key: CDRPUGZCRXZLFL-OWOJBTEDSA-N

    InChi Code: InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+

    SMILES Code: c1(c(ccc(\C=C\c2cc(O)cc(c2)O)c1)O)O


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    In Vitro

    In vitro activity: 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. Piceatannol also potently inhibits PKA, PKC, MLCK, and CDPK with IC50 of 3 μM, 8 μM, 12 μM, and 19 μM, respectively. 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. 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.


    Kinase Assay: 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 Assay: Cells (LNCaP, DU145, and PC-3) 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.

    In VivoOral 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. 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.
    Animal modelFemale BALB/c mice with dextran sulfate sodium (DSS)-induced colitis
    Formulation & DosageDissolved in DMSO, and diluted in corn oil;10 mg/kg; oral administration
    References

    J Biol Chem. 1994 Nov 25;269(47):29697-703.; Int Immunopharmacol. 2008 Dec 10;8(12):1695-702.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Piceatannol

    Int Immunopharmacol. 2008 Dec 10;8(12):1695-702.

    Piceatannol

    Int Immunopharmacol. 2008 Dec 10;8(12):1695-702.

    Piceatannol

    Int Immunopharmacol. 2008 Dec 10;8(12):1695-702.


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