Embelin

Catalog No.S7025 Batch:S7025

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Technical Data

Formula

C17H26O4
Molecular Weight 294.39 CAS No. 550-24-3
Solubility (25°C)* In vitro DMSO 59 mg/mL (200.41 mM)
Ethanol 12 mg/mL (40.76 mM)
Water Insoluble
* <1 mg/ml means slightly soluble or insoluble.
* 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.
* Room temperature shipping (Stability testing shows this product can be shipped without any cooling measures.)

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Biological Activity

Description Embelin (Embelic Acid, NSC 91874), a quinone isolated from the Japanese Ardisia herb, is an inhibitor of X-linked inhibitor of apoptosis (XIAP) with IC50 of 4.1 μM in a cell-free assay.
Targets
5-LO [2]
(Cell-free assay)		 mPGES-1 [2]
(Cell-free assay)		 XIAP [1]
(Cell-free assay)
0.06 μM 0.2 μM 4.1 μM
In 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. This compound inhibits cell growth of both PC-3 and LNCap cells in a dose-dependent manner, with IC50 values of 3.7 and 5.7 μM. While, the toxicity of this chemical in normal PrEC and in WI-38 cells is much lower with IC50 values of 20.1 μM and 19.3 μM. Treatment of PC-3 cells with 25 and 50 μM of this compound for 48 h, 30% and 75% of cells undergo apoptosis, representing approximately 3-and 9-fold increase as compared to untreated cells. [1] It also potently suppresses the biosynthesis of eicosanoids by selective inhibition of 5-lipoxygenase (5-LO) and Microsomal prostaglandin E2 synthase-1 (mPGES-1) with IC50 = 0.06 and 0.2 mM, respectively. [2]

Protocol (from reference)

Kinase Assay:[1]
  • Fluorescence Polarization Competitive Binding Assay

    Fluorescence polarization experiments are 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 are 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 h to reach equilibrium.
Cell Assay:[1]
  • Cell lines

    Human prostate cancer cell lines (PC-3, LNCap), normal human fibroblast cell line WI-38, and humanprostate epithelial cells (PrEC)

  • Concentrations

    1-64 μM

  • Incubation Time

    4-5 days

  • Method

    Cell growth is determined by the MTT-based assay using Cell Proliferation Reagent WST-1 according to the manufacturer’s instruction. Cells (5000 cells/well) are grown in medium with 10% FBS, and various concentrations of this compound are added to the cells. Four to five days later, WST-1 is added to each well and incubated for 1-3 h at 37 °C. Absorbance is measured with a plate reader at 450 nm with correction at 650 nm.

References

  • https://pubmed.ncbi.nlm.nih.gov/15115387/
  • https://pubmed.ncbi.nlm.nih.gov/23623753/

Customer Product Validation

(d) Representative plots of apoptosis in Jurkat cells treated with vehicle only, BIO, CN585, Embelin (Emb), BIO plus CN585 or BIO plus CN585 plus Emb.

Data from [ , , Leukemia, 2016, 812-822. ]

Monocytes were mock or HCMV infected for 24 h, after which infected cells were treated with embelin (a XIAP inhibitor) for an additional 24 h. caspase 3 cleavage was assessed by immunoblotting. Membranes were then reprobed for β-actin as a loading control.

Data from [ , , Antiviral Res, 2018, 158:13-24 ]

Histological evaluation of distal ileum, lung, and liver. CLP led to organ injuries with increased neutrophil infiltration. Embelin treatment resulted in improved morphology in ileum, lung, and liver with reduced neutrophil infiltration (H&E stain, ×200).

Data from [ , , Inflammation, 2015, 38(4): 1556-1562. ]

Inhibition of XIAP by its inhibitor Embelin leads to sensitizing MDA-MB-231 cells to cisplatin.

Data from [ , , EBioMedicine, 2017, 15:48-61 ]

Selleck's Embelin Has Been Cited by 8 Publications

Embelin attenuates lipopolysaccharide-induced acute kidney injury through the inhibition of M1 macrophage activation and NF-κB signaling in mice [ Heliyon, 2023, 9(3):e14006] PubMed: 36938407
Targeting c-IAP1, c-IAP2, and Bcl-2 Eliminates Senescent Glioblastoma Cells Following Temozolomide Treatment [ Cancers (Basel), 2021, 13(14)3585] PubMed: 34298797
SMAC Mimetics Induce Autophagy-Dependent Apoptosis of HIV-1-Infected Resting Memory CD4+ T Cells. [ Cell Host Microbe, 2018, 24(5):689-702] PubMed: 30344003
Aberrant regulation of the Akt signaling network by human cytomegalovirus allows for targeting of infected monocytes [Peppenelli MA Antiviral Res, 2018, 158:13-24] PubMed: 30055197
Porphyromonas gingivalis Differentially Modulates Apoptosome Apoptotic Peptidase Activating Factor 1 in Epithelial Cells and Fibroblasts [Bugueno IM Am J Pathol, 2018, 188(2):404-416] PubMed: 29154960
Regulation of XIAP Turnover Reveals a Role for USP11 in Promotion of Tumorigenesis. [Zhou Z, et al. EBioMedicine, 2017, 15:48-61] PubMed: 28040451
Calcineurin and GSK-3 inhibition sensitizes T-cell acute lymphoblastic leukemia cells to apoptosis through X-linked inhibitor of apoptosis protein degradation. [Tosello V, et al. Leukemia, 2016, 30(4):812-22] PubMed: 26648536
Embelin Reduces Systemic Inflammation and Ameliorates Organ Injuries in Septic Rats Through Downregulating STAT3 and NF-κB Pathways. [Zhou XL, et al. Inflammation, 2015, 38(4):1556-62] PubMed: 25682469

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SHIPPING AND STORAGE
Selleck products are transported at room temperature. If you receive the product at room temperature, please rest assured, the Selleck Quality Inspection Department has conducted experiments to verify that the normal temperature placement of one month will not affect the biological activity of powder products. After collecting, please store the product according to the requirements described in the datasheet. Most Selleck products are stable under the recommended conditions.

NOT FOR HUMAN, VETERINARY DIAGNOSTIC OR THERAPEUTIC USE.