| Identification | Back Directory | [Name]
INDIRUBIN-3'-MONOXIME | [CAS]
160807-49-8 | [Synonyms]
Indirubin-3'
Indirubin-3′
INDIRUBIN-3'-OXIME
Indirubine-3'-oxime
INDIRUBIN-3'-MONOXIME
INDIRUBIN-3’-MONOOXIME
3-[1,3-DIHYDRO-3-(HYDROXYIMINO)-2H-INDOL-2-YLIDENE]-1,3-DIHYDRO-2H-INDOL-2-ONE | [Molecular Formula]
C16H11N3O2 | [MDL Number]
MFCD02683594 | [MOL File]
160807-49-8.mol | [Molecular Weight]
277.28 |
| Chemical Properties | Back Directory | [Appearance]
Dark Red Solid | [Melting point ]
247-249°C | [Boiling point ]
532.2±50.0 °C(Predicted) | [density ]
1.50 | [storage temp. ]
Store at RT | [solubility ]
DMSO: >10 mg/mL
| [form ]
solid
| [pka]
8.66±0.20(Predicted) | [color ]
Dark red or brown | [Stability:]
Light Sensitive | [CAS DataBase Reference]
160807-49-8 |
| Hazard Information | Back Directory | [Chemical Properties]
Dark Red Solid | [Uses]
A potent inhibitor of GSK-3? (IC50=22nM). Also inhibits CDK1 (IC50=180nM) and CDK (IC50=100nM). It reversibly arrests asynchronous HBL-100 cells at G2. It induces apoptosis in the mammary carcinoma cell line MCF-7 (10üM). | [Biological Activity]
Protein kinase inhibitor: inhibits cyclin-dependent kinases (IC 50 = 0.18-3.33 μ M) and GSK-3 β (IC 50 = 0.19 μ M). Inhibits CDK5- and GSK-3 β -mediated tau phosphorylation, a process over-active in Alzheimer disease states. Also inhibits AMPK, LCK and SGK. Induces cell cycle arrest and inhibits cell proliferation. | [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 | [Definition]
ChEBI: Indirubin-3'-monoxime is a member of the class of biindoles that is indirubin in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime. It has a role as an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, an osteogenesis regulator, a neuroprotective agent and an anti-obesity agent. It is a member of oxindoles, a bisindole, a ring assembly, a ketoxime and an alkaloid. | [Biochem/physiol Actions]
Indirubin-3′-oxime is a cyclin-dependent kinase inhibitor which functions by competing with ATP for binding to the catalytic subunit; exhibits antiproliferative activity leading to G2/M arrest in many cell lines and G1/S arrest in Jurkat cells. | [storage]
Store at RT | [References]
1) Leclerc?et al. (2001),?Indirubins inhibit glycogen synthase kinase-3 beta 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?251
2) Damiens?et al. (2001),?Anti-mitotic properties of indirubin-3′-monoximine, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest; Oncogene,?20?3786
3) Kim?et al. (2011),?Indirubin-3′-monoxime, a derivative of a chinese antileukemia medicine, inhibits angiogenesis; J. Cell. Biochem.,?112?1384
4) Ding?et al. (2010),?Indirubin-3′-monoxime rescues spatial memory deficits and attenuates beta-amyloid-associated neuropathology in a mouse model of Alzheimer’s disease; Neurobiol. Dis.,?39?156 |
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