Embelin

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Cat.No. 2156 - Embelin | C17H26O4 | CAS No. 550-24-3
Description: Inhibitor of X-linked inhibitor of apoptosis (XIAP); cell-permeable and antitumor
Chemical Name: 2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione
Purity: ≥98% (HPLC)
Datasheet
Citations (1)
Reviews
Literature (2)
Pathways (1)

Biological Activity

Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 μM in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC50 4 - 6 μM), but has a weaker effect on normal prostate cells (IC50 = 19 - 20 μM). Overcomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo.

Technical Data

M. Wt 294.39
Formula C17H26O4
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 550-24-3
PubChem ID 3218
InChI Key IRSFLDGTOHBADP-UHFFFAOYSA-N
Smiles OC=1C(=O)C(CCCCCCCCCCC)=C(C(=O)C1)O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 2.94 10 with gentle warming
DMSO 29.44 100

Preparing Stock Solutions

The following data is based on the product molecular weight 294.39. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.4 mL 16.98 mL 33.97 mL
5 mM 0.68 mL 3.4 mL 6.79 mL
10 mM 0.34 mL 1.7 mL 3.4 mL
50 mM 0.07 mL 0.34 mL 0.68 mL

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References

References are publications that support the biological activity of the product.

Chitra et al (1994) Antitumor, anti-inflammatory and analgesic property of embelin, a plant product. Chemotherapy 40 109 PMID: 7510605

Nikolovska-Coleska et al (2004) 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. 47 2430 PMID: 15115387

Modak et al (2013) Probing p300/CBP associated factor (PCAF)-dependent pathways with a small molecule inhibitor. ACS Chem.Biol. 8 1311 PMID: 23570531


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Keywords: Embelin, Embelin supplier, inhibitors, inhibits, X-linked, apoptosis, XIAP, cell-permeable, antitumor, c-IAP, Inhibitor, of, Apoptosis, (IAP), 2156, Tocris Bioscience

1 Citation for Embelin

Citations are publications that use Tocris products. Selected citations for Embelin include:

Barbelanne et al (2013) Pathogenic NPHP5 mutations impair protein interaction with Cep290, a prerequisite for ciliogenesis. Hum Mol Genet 22 2482 PMID: 23446637


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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* or download your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Programmed Cell Death

Programmed Cell Death Poster

There are two currently recognized forms of programmed cell death: apoptosis and necroptosis. This poster summarizes the signaling pathways involved in apoptosis, necroptosis and cell survival following death receptor activation, and highlights the influence of the molecular switch, cFLIP, on cell fate.

Pathways for Embelin

Apoptosis

Apoptosis Signaling Pathway

Apoptosis is a physiological process for cell death that is critical during aging and development. It may also be referred to as cell 'suicide'. Apoptosis can be triggered by events both inside and outside of the cell.