Embelin

Alias: Embelic acid; NSC91874; NSC91874; Embelin; NSC 91874; Emberine
Cat No.:V0054 Purity: ≥98%
Embelin is a naturally occuring quinone compound isolated from the Japanese Ardisia herb with anti-tumor and anti-inflammatory activity, acting as a potent andcell-permeable inhibitor of XIAP (X-linked inhibitor of apoptosis) with IC50 of 4.1 μM in cell-free assays.
Embelin Chemical Structure CAS No.: 550-24-3
Product category: IAP
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Embelin is a naturally occurring quinone compound that was isolated from the Japanese herb Ardisia. It has anti-tumor and anti-inflammatory properties, and it also functions as a powerful and cell-permeable inhibitor of XIAP (X-linked inhibitor of apoptosis), with an IC50 value of 4.1 μM in cell-free assays.

Biological Activity I Assay Protocols (From Reference)
Targets
5-LO (IC50 = 0.06 μM); mPGES-1 (IC50 = 0.2 μM); XIAP (IC50 = 4.1 μM)
ln Vitro
Embelin from the Japanese Ardisia herb is a small-molecular inhibitor that binds to the XIAP BIR3 domain with which Smac and caspsase-9 bind. Embelin has IC50 values of 3.7 and 5.7 μM and inhibits PC-3 and LNCap cell growth in a dose-dependent manner. While Embelin's toxicity in normal PrEC and WI-38 cells is much lower, with IC50 values of 20.1 μM and 19.3 μM, respectively. When PC-3 cells are treated for 48 hours with 25 and 50 μM of embelin, 30% and 75% of the cells die, which is an increase of about 3 and 9 times more than in untreated cells.[1] Embelin selectively inhibits 5-lipoxygenase (5-LO) and Microsomal prostaglandin E2 synthase-1 (mPGES-1) with IC50 values of 0.06 and 0.2 mM, respectively, to suppress the biosynthesis of eicosanoids.[2]
ln Vivo
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 proliferation of tumor epithelial cells and suppressing IL6 expression and IL6-activated STAT3 in vivo.
Enzyme Assay
Fluorescence polarization experiments are performed in Dynex 96-well, black, round-bottom plates. A final volume of 125 L is created by adding a 5 μL sample of Embelin dilutions in DMSO, preincubated XIAP BIR3 protein (0.06 M), and the N terminus of a Smac peptide (SM7F) (0.01 M) in the assay buffer. Both the bound peptide control (equivalent to 0% inhibition) and the free peptide control (equivalent to 100% inhibition) were used in each assay. The bound peptide control contained XIAP BIR3 protein and SM7F. To achieve equilibrium, the plates were combined and incubated for 3 hours at room temperature.
Cell Assay
The MTT-based assay, which uses Cell Proliferation Reagent WST-1 in accordance with the manufacturer's instructions, is used to measure cell growth. Cells (5000 cells/well) are grown in medium containing 10% FBS and different concentrations of Embelin. WST-1 is added to each well and incubated for 1-3 hours at 37 °C four to five days later. A plate reader is used to measure absorbance at 450 nm with a correction at 650 nm.
Animal Protocol
50 mg/kg/day; p.o.
AOM/DSS-induced colitis-associated cancer (CAC) model
References

[1]. J Med Chem . 2004 May 6;47(10):2430-40.

[2]. Biochem Pharmacol . 2013 Aug 15;86(4):476-86.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H26O4
Molecular Weight
294.39
Exact Mass
294.18311
Elemental Analysis
C, 69.36; H, 8.90; O, 21.74
CAS #
550-24-3
Related CAS #
550-24-3
Appearance
Solid powder
SMILES
CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O
InChi Key
IRSFLDGTOHBADP-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
Chemical Name
2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
Synonyms
Embelic acid; NSC91874; NSC91874; Embelin; NSC 91874; Emberine
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

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: ~59 mg/mL (~200.4 mM)
Water: <1 mg/mL (slightly soluble or insoluble)
Ethanol: ~12 mg/mL (~40.8 mM)
Preparing Stock Solutions 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

*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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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.

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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT06042647 Active
Recruiting
Drug: 0.01% Halobetasol
Drug: 0.045% Tazarotene
Psoriasis Vulgaris Dermatology Consulting
Services, PLLC
July 13, 2023 Phase 4
NCT03926299 Active
Recruiting
Device: FotonaSmooth SP®
Spectro laser device
Drug: Clobetasol propionate
0.05% ointment
Chronic Skin Disease
Vulvar Lichen Sclerosus
Prof. Dr. Volker Viereck July 15, 2019 Not Applicable
NCT01893567 Completed Drug: Clobex Spray Plaque Psoriasis Galderma R&D July 2013 Phase 4
NCT00852761 Completed Drug: Olux-E Foam
Drug: Clobex lotion
Plaque-Type Psoriasis Stiefel, a GSK Company March 2009 Phase 4
NCT00715975 Completed Drug: halobetasol
Drug: clobetasol
Psoriasis Azidus Brasil July 2008 Phase 2
Phase 3
Biological Data
  • Embelin
    Oncol Lett. 2015 Aug;10(2):921-926.
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