BIO
Item № 13123
CAS № 667463-62-9
Purity ≥98%
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1 mg $25.00 $0.00
5 mg $99.00 $0.00
10 mg $138.00 $0.00
25 mg $313.00 $0.00

Pricing updated 2015-09-05. Prices are subject to change without notice.

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Description
Synonyms
  • MLS 2052
  • ​GSK3 Inhibitor IX
  • 6-Bromoindirubin-3'-oxime

BIO is a cell-permeable bis-indolo (indirubin) compound that acts as a highly potent, selective, reversible, and ATP-competitive inhibitor of GSK3α/β (IC50 = 5 nM). 1,2 Its specificity has been tested against various cyclin-dependent kinases (CDKs) (IC50s = 83, 300, 320, and 10,000 nM for Cdk5/p25, Cdk2/A, Cdk1/B, and Cdk4/D1, respectively). BIO was also tested for its specificity towards many other commonly studied kinases (IC50 ≥10 µM), including MAP kinases, PKA, PKC isoforms, PKG, CK, and IRTK. 1,2 Inhibition of GSK by BIO has been shown to result in the activation of the Wnt signaling pathway and sustained pluripotency in human and mouse embryonic stem cells (ESCs).3 BIO is reported to maintain self-renewal in human and mouse ESCs as well as induce the differentiation of neonatal cardiomyocytes.4

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Technical Information
Formal Name 6-​bromo-​3-​[(3E)-​1,​3-​dihydro-​3-​(hydroxyimino)-​2H-​indol-​2-​ylidene]-​1,​3-​dihydro-​(3Z)-​2H-​indol-​2-​one
CAS Number 667463-62-9
Synonyms
  • MLS 2052
  • ​GSK3 Inhibitor IX
  • 6-Bromoindirubin-3'-oxime
Molecular Formula C16H10BrN3O2
Formula Weight 356.2
Purity ≥98%
Formulation A crystalline solid
λmax 224, 254, 281, 291, 330, 344, 503 nm
SMILES O/N=C1/C(=C2\C(=O)​Nc3cc(Br)​ccc/23)​\Nc2ccccc\12
InChI Code ​1S/C16H10BrN3O2/c17-8-5-6-9-12(7-8)​19-16(21)​13(9)​15-14(20-22)​10-3-1-2-4-11(10)​18-15/h1-7,18,22H,(H,19,21)​/b15-13-,20-14+
InChI Key DDLZLOKCJHBUHD-WAVHTBQISA-N

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability 2 years
Product Downloads & Resources
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Download Product Insert 109 Kb PDF

Download Safety Data Sheet (SDS) 27 Kb PDF

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Additional Information

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References & Background Reading
Product Description References

1. Meijer, L., Skaltsounis, A., Magiatis, P., et al. GSK-3-selective inhibitors derived from tyrian purple indirubins. Chem Biol 10 1255-1266 (2003).

2. Polychronopoulos, P., Magiatis, P., Skaltsounis, A., et al. Structural basis for the synthesis of indirubins as potent and selective inhibitors of glycogen synthase kinase-3 and cyclin-dependent kinases. J Med Chem 47 935-946 (2004).

3. Sato, N., Meijer, L., Skaltsounis, L., et al. Maintenance of pluripotency in human and mouse embryonic stem cells through activation of Wnt signaling by a pharmacological GSK-3-specific inhibitor. Nat Med 10(1) 55-63 (2004).

4. Tseng, A., Engel, F.B., and Keating, M.T. The GSK-3 inhibitor BIO promotes proliferation in mammalian cardiomyocytes. Chem Biol 13 957-963 (2006).

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