Indirubin-3'-monoxime

Cayman Chemical Item Number 13314

(CAS 160807-49-8)

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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

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? J Biol Chem 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 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).

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
Formulation A crystalline solid
Purity ≥98%
λmax 212, 252, 280, 286, 328, 342, 502 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O/N=C1\C(=C2/C(=O)​Nc3ccccc\23)​/Nc2ccccc/12
InCHI Code
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​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
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HBDSHCUSXQATPO-BGBJRWHRSA-N

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Size Price Quantity Subtotal
1 mg $38.00 $0.00
5 mg $76.00 $0.00
10 mg $133.00 $0.00
50 mg $570.00 $0.00
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