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178493

Sigma-Aldrich

Apoptosis Activator III, Embelin

The Apoptosis Activator III, Embelin, also referenced under CAS 550-24-3, controls the biological activity of Apoptosis. This small molecule/inhibitor is primarily used for Cancer applications.

Synonym(s):

Apoptosis Activator III, Embelin, Embelin, Embelia ribes, XIAP inhibitor, Embelin, 2,5-Dihydroxy-3-undecyl-1,4-benzoquinone

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About This Item

Empirical Formula (Hill Notation):
C17H26O4
CAS Number:
550-24-3
Molecular Weight:
294.39
MDL number:
MFCD00016369
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

orange

solubility

DMSO: 10 mg/mL
methanol: 5 mg/mL

shipped in

ambient

storage temp.

2-8°C

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

InChI key

IRSFLDGTOHBADP-UHFFFAOYSA-N

General description

A cell-permeable benzoquinone compound that exhibits antitumor properties. Specifically antagonizes XIAP (X-linked inhibitor of apoptosis)-mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 (IC50 = 4.1 µM in a competitive binding assay with Smac peptide). Selectively induces caspase-9-mediated apoptosis in prostate cancer cells with high levels of XIAP (IC50 = 3.7 and 5.7 µM for PC-3 and LnCap, respectively), while exhibiting much less effect towards cells with low level XIAP (IC50 = 19.3 and 20.1 µM for WI-38 and PrEC, respectively). Also shown to sensitize XIAP overexpressing Jurkat cells to Etoposide -induced apoptosis. A non-competitive PCAF (p300/CBP associated factor)-specific lysine acetyltransferase (KAT) inhibitor (IC50 = 7.2 µM).
A cell-permeable, benzoquinone compound that exhibits anti-tumor properties. Shown to specifically antagonize X-linked inhibitor of apoptosis- (XIAP) mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 (IC50 = 4.1 µM in a competitive binding assay using Smac peptide). Also selectively induces caspase-9-mediated apoptosis in prostate cancer cells expressing high levels of XIAP (IC50 = 3.7 µM for PC-3 cells and 5.7 µM for LnCap cells), while exhibiting lesser effects toward cells with low levels of XIAP (IC50 = 19.3 µM for WI-38 cells and 20.1 µM for PrEC cells). Reported to sensitize XIAP-overexpressing Jurkat cells to Etoposide- (Cat. No. 341245) induced apoptosis. A non-competitive PCAF (p300/CBP associated factor)-specific lysine acetyltransferase (KAT) inhibitor (IC50 = 7.2 µM).

Biochem/physiol Actions

Cell permeable: yes
Primary Target
BIR3
Product does not compete with ATP.
Reversible: no
Target IC50: 4.1 µM in antagonizing XIAP (X-linked inhibitor of apoptosis)-mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 in a competitive binding assay with Smac peptide

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Analysis Note

Single spot by TLC

Other Notes

Modak, R., et al. 2013. ACS Chem. Biol.8, In press.
Nikolovska-Coleska, Z., et al. 2004. J. Med. Chem.47, 2430.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361f

Hazard Classifications

Repr. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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