Embelin (Synonyms: Embelic acid; Emberine; NSC 91874) |
| Catalog No.GC13163 |
A benzoquinone with diverse biological activities
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 550-24-3
Sample solution is provided at 25 µL, 10mM.
Embelin, a natural benzoquinone from plants of the genus Embelia, is an inhibitor of X-linked inhibitor of apoptosis protein (XIAP) with IC50 of 4.1 μM.
XIAP is a member of the inhibitor of apoptosis family of proteins. This protein modulates signaling pathways involved in cell apoptosis and stops cell apoptosis induced by viral infection or overproduction of caspases.
Embelin was shown to exhibit anti-tumor and anti-inflammatory activity in cells. For instance, embelin inhibits cell growth and activates caspases to promote apoptosis in cancer cells with high expression of XIAP [1]. Additionally, embelin was reported to prevent NF-κB activation by inhibiting IKK and thus resulted in suppression of NF-κB-regulated anti-apoptotic and metastatic gene expression [2].
Embelin has also been used extensively in various animal models to study the role of XIAP. In the azoxymethane/dextran sulfate sodium (AOM/DSS) induced colitis-associated cancer (CAC) model, embelin reduced both incidence and tumor size in mice by inhibiting the proliferation of tumor epithelial cells and suppressing IL6 expression and IL6-activated STAT3 in vivo [3].
References:
[1]. Nikolovska-Coleska Z, Xu L, Hu Z, Tomita Y, Li P, Roller PP, et al. Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database. J Med Chem 2004,47:2430-2440.
[2]. Ahn KS, Sethi G, Aggarwal BB. Embelin, an inhibitor of X chromosome-linked inhibitor-of-apoptosis protein, blocks the nuclear factor-kappaB (NF-kappaB) signaling pathway leading to suppression of NF-kappaB-regulated antiapoptotic and metastatic gene products. Mol Pharmacol 2007,71:209-219.
[3].Dai Y, Jiao H, Teng G, Wang W, Zhang R, Wang Y, et al. Embelin reduces colitis-associated tumorigenesis by limiting IL-6/STAT3 signaling. Mol Cancer Ther 2014,13:1206-1216.
| Kinase experiment [1]: | |
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Fluorescence polarization competitive binding assay |
Fluorescence polarization experiments were performed in Dynex 96-well, black, round-bottom plates. A 5 μL sample of Embelin dilutions in DMSO, and preincubated XIAP BIR3 protein (0.06 μM) and the N terminus of a Smac peptide (SM7F) (0.01 μM) in the assay buffer were added to 96-well plates to produce a final volume of 125 μL. For each assay, the bound peptide control containing XIAP BIR3 protein and SM7F (equivalent to 0% inhibition) and free peptide control containing only free SM7F (equivalent to 100% inhibition) were included. The plates were mixed and incubated at room temperature for 3 hrs to reach equilibrium. |
| Cell experiment [1]: | |
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Cell lines |
PC-3, LNCap, PrEC and WI-38 cells |
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Preparation method |
The solubility of this compound in DMSO is >10 mM. 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. |
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Reaction Conditions |
1 ~ 64 μM; 4 ~ 5 days |
|
Applications |
Embelin dose-dependently inhibited cell growth of both PC-3 and LNCap cells, with the IC50 values of 3.7 and 5.7 μM, respectively. In normal PrEC and WI-38 cells, the toxicity of Embelin was much lower, with the IC50 values of 20.1 μM and 19.3 μM, respectively. |
| Animal experiment [2]: | |
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Animal models |
AOM/DSS-induced colitis-associated cancer (CAC) model |
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Dosage form |
50 mg/kg/day; p.o. |
|
Applications |
In a CAC model, Embelin reduced both incidence and tumor size in mice by inhibiting proliferation of tumor epithelial cells and suppressing IL6 expression and IL6-activated STAT3. |
|
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. |
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References: [1]. Nikolovska-Coleska Z, Xu L, Hu Z, Tomita Y, Li P, Roller PP, et al. Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database. J Med Chem 2004,47:2430-2440. [2]. Dai Y, Jiao H, Teng G, Wang W, Zhang R, Wang Y, et al. Embelin reduces colitis-associated tumorigenesis through limiting IL-6/STAT3 signaling. Mol Cancer Ther 2014,13:1206-1216. | |
| Cas No. | 550-24-3 | SDF | |
| Synonyms | Embelic acid; Emberine; NSC 91874 | ||
| Chemical Name | 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione | ||
| Canonical SMILES | CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O | ||
| Formula | C17H26O4 | M.Wt | 294.39 |
| Solubility | ≥ 9.6mg/mL in DMSO, ≥ 4.23 mg/mL in EtOH with ultrasonic | Storage | 4°C, protect from light |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.3969 mL | 16.9843 mL | 33.9685 mL |
| 5 mM | 0.6794 mL | 3.3969 mL | 6.7937 mL |
| 10 mM | 0.3397 mL | 1.6984 mL | 3.3969 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
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Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 30 reference(s) in Google Scholar.)
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