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Wogonin

Alias: Vogonin
Cat No.:V1184 Purity: ≥98%
Wogonin (Vogonin), a naturally occurring and pharmacologically-active flavonoid found in plants, has been reported to exhibit anticancer effects against various cancer cell types such as osteosarcoma, leukemia, breast cancer and glioma.
Wogonin
Wogonin Chemical Structure CAS No.: 632-85-9
Product category: ROCK
This product is for research use only, not for human use. We do not sell to patients.
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25mg
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Wogonin (Vogonin), a naturally occurring and pharmacologically-active flavonoid found in plants, has been reported to exhibit anticancer effects against various cancer cell types such as osteosarcoma, leukemia, breast cancer and glioma. Wogonin induced a G1 phase cell cycle arrest in HCT116 cells in a concentration- and time-dependent manner. Meanwhile, the cell cycle-related proteins, such as cyclin A, E, D1, and CDK2, 4 were down-regulated in wogonin-induced G1 cell cycle arrest. Furthermore, we showed that the anti-proliferation and G1 arrest effect of wogonin on HCT116 cells was associated with deregulation of Wnt/β-catenin signaling pathway.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
In caco-2, SW1116, and HCT116 cells, wogonin (0-200 μM) shows a dose- and time-dependent reduction in cell viability. In HCT-116 cells, wogonin (10–40 μM) causes G1 phase arrest. In HCT116 cells, wogonin also inhibits the Wnt signaling pathway. Wogonin interferes with the TCF/Lef family transcription factor's function. Furthermore, Wogonin suppresses CDK8 activity to prevent β-catenin-mediated transcription[1]. On HeLa cells, wogonin exhibits cytotoxic and antiproliferative properties. In HeLa cells, wogonin (90 µM) significantly reduces the levels of cyclin D1 and Cdk4, and causes cell cycle arrest at the G0-G1 phase[2]. In RAW264.7 cells, wogonin (1.25, 2.5, 5, 10, 20 μg/ml) inhibits the inflammatory response triggered by EtOH[3].
ln Vivo
Wogonin (30, 60 mg/kg) inhibits HCT116 cell tumor growth in a xenograft model[1]. Wogonin (25, 50, and 100 mg/kg) shields mice's livers from damage and the pathological features of ALD. In mice with ALD and RAW264.7 cells induced by EtOH, wogonin stimulates the expression of PPAR-γ[3].
Animal Protocol
N/A
Mice
References
[1]. He L, et al. Wogonin induced G1 cell cycle arrest by regulating Wnt/β-catenin signaling pathway and inactivating CDK8 in human colorectal cancer carcinoma cells. Toxicology. 2013 Oct 4;312:36-47.
[2]. Yang L, et al. Wogonin induces G1 phase arrest through inhibiting Cdk4 and cyclin D1 concomitant with an elevation in p21Cip1 in human cervical carcinoma HeLa cells. Biochem Cell Biol. 2009 Dec;87(6):933-42.
[3]. Li HD, et al. Wogonin attenuates inflammation by activating PPAR-γ in alcoholic liver disease. Int Immunopharmacol. 2017 Sep;50:95-106
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H12O5
Molecular Weight
284.26
CAS #
632-85-9
Related CAS #
51059-44-0 (Wogonoside)
Appearance
Typically exists as solids (or liquids in special cases) at room temperature
SMILES
O1C(C2C([H])=C([H])C([H])=C([H])C=2[H])=C([H])C(C2C(=C([H])C(=C(C1=2)OC([H])([H])[H])O[H])O[H])=O
InChi Key
XLTFNNCXVBYBSX-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3
Chemical Name
4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-methoxy-2-phenyl-
Synonyms
Vogonin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:56 mg/mL (197.0 mM)
Water:<1 mg/mL
Ethanol:8 mg/mL (28.1 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.08 mg/mL (7.32 mM) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 24 mg/mL (84.43 mM) in 0.5% CMC-Na/saline water (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.5179 mL 17.5895 mL 35.1791 mL
5 mM 0.7036 mL 3.5179 mL 7.0358 mL
10 mM 0.3518 mL 1.7590 mL 3.5179 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Wogonin inhibits transcription and downregulates expression of the anti-apoptotic protein Mcl-1 in malignant cells. (a) Wogonin downregulates Mcl-1 protein expression in malignant cells. CEM, HTLV-1-SP and HCT116 cells were treated with 50 μM wogonin for indicated time periods. The expression levels of the indicated proteins were examined by western blot analysis. Data are representative of two independent experiments. (b and c) Wogonin downregulates Mcl-1 and Bcl-2 mRNA expression in malignant cells. CEM cells were treated with 50 μM wogonin for indicated time periods. Mcl-1 and Bcl-2 mRNA expression levels were examined by real-time PCR. Means±S.D. are shown. Data are representative of three independent experiments performed in triplicates. (d) Wogonin suppresses RNA synthesis in malignant cells. CEM cells were treated with different concentrations of wogonin for 6 h as indicated. RNA synthesis was measured by [3H]-uridine-incorporation. Means±S.D. are shown. Data are representative of two independent experiments performed in triplicates. Polier G, et al. Cell Death Dis. 2011, 2:e182.
  • Wogonin is a naturally occurring inhibitor of CDK7 and CDK9. (a) Wogonin inhibits phosphorylation of the CTD of RNAPII at Ser2 and Ser5 sites. CEM cells were treated with different concentrations of wogonin for 2 h (left panel) or for different time periods with 50 μM wogonin (right panel) and the cells were analyzed for the status of RNAPII phosphorylation by western blot analysis using antibodies specific for phosphorylated CTD of RNAPII Ser2 and Ser5 sites. One representative experiment of three is shown. (b) Wogonin does not inhibit phosphorylation of the retinoblastoma (RB) protein. CEM cells were treated with 50 μM wogonin (Wogo) for 3 h. Cells were lysed and total RB was immunoprecipitated and phosphorylated RB was examined by western blot using phospho-specific antibodies as indicated (left panel). As a control, the same cell lysates were analyzed for the status of phosphorylation of RNAPII at the Ser2 residue (right panel). Data are representative of three independent experiments. (c) Wogonin inhibits CDK7 and CDK9 kinase activity determined by incorporation of [33P]. CDK7/cyclinH/MAT1 or CDK9/cyclinT was incubated with substrate peptide and [33P]-ATP in the presence of different doses of wogonin as indicated. The kinase activity is described as % of [33P]-phosphorylated substrate peptide. Means±S.D. are shown. The half-maximal inhibitory concentrations (IC50) are indicated. Polier G, et al. Cell Death Dis. 2011, 2:e182.
  • In silico docking analysis of wogonin on the crystal structure of CDK9. (a) Computer docking simulation of the crystal structure of human CDK9 in complex with wogonin. (b) MultiBind webserver analysis predicted wogonin-binding residues in CDK9. The residues involved in the binding of wogonin to CDK9 are indicated by triangles. Polier G, et al. Cell Death Dis. 2011, 2:e182.
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