178493

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.

• Sinónimos: Apoptosis Activator III, Embelin, Embelin, Embelia ribes, XIAP inhibitor, Embelin, 2,5-Dihydroxy-3-undecyl-1,4-benzoquinone
• Fórmula empírica (notación de Hill): C₁₇H₂₆O₄
• Número de CAS: 550-24-3
• Peso molecular: 294.39
• Número MDL: MFCD00016369
• Código UNSPSC: 12352200
• NACRES: NA.77

Propiedades

• Nivel de calidad: 100
• Formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: orange
• solubilidad: DMSO: 10 mg/mL; methanol: 5 mg/mL
• Condiciones de envío: ambient
• temp. de almacenamiento: 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
• Clave InChI: IRSFLDGTOHBADP-UHFFFAOYSA-N

Descripción

Descripción general

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).

Acciones bioquímicas o fisiológicas

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

Envase

Packaged under inert gas

Advertencia

Toxicity: Standard Handling (A)

Nota de análisis

Single spot by TLC

Otras notas

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

Información legal

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

Información de seguridad

• Pictogramas: GHS08
• Palabra de señalización: Warning
• Frases de peligro: H361f
• Consejos de prudencia: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Clasificaciones de peligro: Repr. 2
• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable