Inhibitor of GSK3β and cyclin-dependent kinases
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Indirubin-3'-monoxime

Item No. 13314

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[1,3-dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one
CAS Number
160807-49-8
Molecular Formula
C16H11N3O2
Formula Weight
277.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:5): 0.15 mg/mlEthanol: 2 mg/ml
λmax
212, 252, 280, 286, 328, 342, 502 nm
SMILES
O/N=C1\C(=C2/C(=O)Nc3ccccc\23)/Nc2ccccc/12
InChi Code
InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17,21H,(H,18,20)/b15-13-,19-14+
InChi Key
HBDSHCUSXQATPO-BGBJRWHRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Indirubin-3’-oxime is a potent inhibitor of glycogen synthase kinase 3β (GSK3β; IC50 = 22 nM).1 As GSK3β phosphorylates tau protein, indirubin-3’-oxime prevents tau phosphorylation both in vitro and in vivo at Alzheimer’s disease-relevant sites.1 It also inhibits cyclin-dependent kinases (CDKs) at higher concentrations, including Cdk1/cyclin B (IC50 = 180 nM), Cdk2/cyclin A (IC50 ~500 nM), Cdk2/cyclin E (IC50 = 250nM), Cdk4/cyclin D1 (IC50 = 3.3 µM) and Cdk5/p35 (IC50 = 100 nM). Indirubin-3’-oxime reversibly inhibits the proliferation of many cells types, arresting cycling in the G2/M phase.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. LeClerc, S., Garnier, M., Hoessel, R., et al. Indirubins inhibit glycogen synthase kinase-3β and CDK5/P25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer’s disease. A property common to most cyclin-dependent kinase inhibitors? The Journal of Biological Chemisty 276(1), 251-260 (2001).

    2. Damiens, E., Baratte, B., Marie, D., et al. Anti-mitotic properties of indirubin-3'-monoxime, a CDK/GSK-3 inhibitor: Induction of endoreplication following prophase arrest. Oncogene 20(29), 3786-3797 (2001).

    3. Marko, D., Schätzle, S., Friedel, A., et al. Inhibition of cyclin-dependent kinase 1 (CDK1) byindirubin derivatives in human tumour cells. Br. J. Cancer 84(2), 283-289 (2001).