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361551

Sigma-Aldrich

GSK-3 Inhibitor X

The GSK-3 Inhibitor X, also referenced under CAS 740841-15-0, controls the biological activity of GSK-3. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.

Synonym(s):

GSK-3 Inhibitor X, (2ʹZ,3ʹE)-6-Bromoindirubin-3ʹ-acetoxime, BIO-Acetoxime

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About This Item

Empirical Formula (Hill Notation):
C18H12BrN3O3
CAS Number:
Molecular Weight:
398.21
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

Assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

dark purple

solubility

DMSO: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

General description

An acetoxime analog of BIO, GSK-3 Inhibitor IX (Cat. No. 361550) that exhibits greater selectivity for GSK-3α/β (IC50 = 10 nM) over Cdk5/p25, Cdk2/A and Cdk1/B (IC50 = 2.4 µM, 4.3 µM and 63 µM, respectively). Weakly affects the activities of Cdk4/D1 and many other kinases (IC50 ≥ 10 µM). Also acts as an aryl hydrocarbon receptor agonist in both yeast (EC50 ≥ 0.1 µM) and mammalian (EC50 = 0.16 µM) reporter systems.
An acetoxime analog of BIO, GSK-3 Inhibitor IX (Cat. No. 361550) that exhibits greater selectivity for GSK-3α/β (IC50 = 10 nM) over Cdk5/p25, Cdk2/cyclin A, and Cdk1/cyclin B (IC50 = 2.4 µM, 4.3 µM, and 63 µM, respectively). A weak inhibitor of Cdk4/cyclin D1 and many other non-related kinases (IC50 ≥ 10 µM). Yields BIO (Cat. No. 361550) upon hydrolysis.

Biochem/physiol Actions

Cell permeable: no
Primary Target
GSK-3α/β
Product does not compete with ATP.
Reversible: no
Target IC50: 10 nM against GSK-3α/β

Packaging

Packaged under inert gas

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Preparation Note

Limited solubility in aqueous buffers; serial dilutions in DMSO may be required prior to dilution in buffer.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Knockaert, M., et al. 2004. Oncogene23, 4400.
Polychronopoulos, P., et al. 2004. J. Med. Chem.47, 935.
Meijer, L., et al. 2003. Chem. Biol.10, 1255.

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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Noboru Sato et al.
Methods in molecular biology (Clifton, N.J.), 331, 115-128 (2006-08-03)
This chapter introduces a new method of maintaining human embryonic stem cells (hESCs) in the undifferentiated state through treatment with a GSK-3 inhibitor, BIO, under a feeder-free condition. Additionally, methods are introduced that determine multidifferentiation potential of hESCs by differentiating

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