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About This Item

Empirical Formula (Hill Notation):
C24H21N3O6S2
CAS Number:
810659-53-1
Molecular Weight:
511.57
MDL number:
MFCD09037524
UNSPSC Code:
12352200
NACRES:
NA.77
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Quality Level

100

Assay

≥90% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

red

solubility

DMSO: 5 mg/mL
ethanol: 5 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

[s]1c2c(nc1Nc4ccc(cc4)OC(=O)C(NC(=O)OC)CCSC)C(=O)c3c(cccc3)C2=O

InChI

1S/C24H21N3O6S2/c1-32-24(31)26-17(11-12-34-2)22(30)33-14-9-7-13(8-10-14)25-23-27-18-19(28)15-5-3-4-6-16(15)20(29)21(18)35-23/h3-10,17H,11-12H2,1-2H3,(H,25,27)(H,26,31)

InChI key

SFDSXIZFOOBDMC-UHFFFAOYSA-N

General description

A cell-permeable molecule that targets the BH3•domain interaction and selectively induces apoptosis in Bcl-2-overexpressing cells (<300 nM in MDA-MB435B breast cancer cells). Exhibits little effect on a variety of primary cells and Bcl-xL-dependent cells, even at a concentrations as high as 5 µM. Inhibits the binding of Bid BH3 to Bcl-2 thereby blocking the anti-apoptotic activity of Bcl-2.
A cell-permeable naphthoquinone compound that selectively induces apoptosis of Bcl-2-overexpressing cells (<300 nM in MDA-MB435B breast cancer cells) with little effect on a variety of primary cells, and Bcl-xL-dependent cells, even at a concentration of 5 µM. Preferentially binds Bcl-2 (Ki = 1.3 µM) and disrupts its interaction with Bid BH3, thereby blocking the anti-apoptotic activity of Bcl-2. Shown to induce the release of cytochrome c from mitochondria and activate caspase-9.

Biochem/physiol Actions

Cell permeable: yes
Product does not compete with ATP.
Reversible: no
Target Ki: 1.3 µM in binding Bcl-2

Packaging

Packaged under inert gas

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Other Notes

Real, P.J., et al. 2004. Cancer Res. 64, 7947.

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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