Sign Into View Organizational & Contract Pricing
About This Item
Empirical Formula (Hill Notation):
C17H26O4
CAS Number:
Molecular Weight:
294.39
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Quality Level
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
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.
Nikolovska-Coleska, Z., et al. 2004. J. Med. Chem.47, 2430.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Repr. 2
Storage Class Code
11 - Combustible Solids
WGK
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’.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service