Indirubin-3'-monoxime

SKU: orb1302001

Description

Indirubin-3'-monoxime is a potent, cell-permeable small molecule inhibitor of GSK3β (IC50: 22 nM) and several cyclin-dependent kinases (CDKs). It is widely used in biochemical and cellular research to study Wnt/β-catenin signaling, cell cycle progression, and neuronal differentiation in both in vitro and in vivo models.

Research Area

Cell Biology, Metabolism Research, Signal Transduction, Stem Cell & Developmental Biology

Key Properties

• CAS Number: 160807-49-8
• MW: 277.28
• Purity: 99.65%
• Formula: C₁₆H₁₁N₃O₂
• SMILES: ON=C1C(Nc2ccccc12)=C1C(=O)Nc2ccccc12
• Target: GSK-3,CDK,Lipoxygenase
• Solubility: 10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (7.21 mM);H2O:Insoluble;Ethanol:15 mg/mL (54.1 mM);DMSO:55 mg/mL (198.36 mM)

Bioactivity

• Target IC50:
  CDK2-CyclinE:250 nM (cell free)|CDK5-p25:100 nM (cell free)|5-LOX:7.8-10 μM|CDK1-CyclinB:180 nM (cell free)|GSK-3β:22 nM (cell free)
• In Vivo:
  The mice treated with IMX showed a significant reduction in plasma glucose, triglycerides, cholesterol, insulin levels and improvement in learning and memory performance, attenuated the oxidative stress and AChE activity. Moreover, IMX dose-dependently augments the brain insulin and BDNF levels in HFD fed mice .
• In Vitro:
  Indirubins are powerful inhibitors (IC50: 5-50 nM) of GSK-3 beta. Bacterially expressed recombinant human tau was indeed phosphorylated in vitro by GSK-3β, and this phosphorylation was inhibited in a dose-dependent manner by indirubin-3′-monoxime, with an IC50 value of around 100 nM . Indirubin-3'-monoxime reversibly arrests asynchronous HBL-100 cells in G2. Indirubin-3'-monoxime inhibits the phosphorylation of consensus CDK phosphorylation sites as well as of nucleolin at a specific CDK1/cyclin B phosphorylation site . In cell-based and cell-free assays, Indirubin-3'-monoxime selectively inhibited 5-lipoxygenase (5-LO), the key enzyme in LT biosynthesis, with an IC50 in the low micromolar range .
• Cell Research:
  To determine the effects of aminopurvalanol and indirubin-3′-monoxime on tau phosphorylation, Sf9 cells infected with baculovirus expressing htau23 protein were treated 36 h post-infection (when cells have already expressed levels of tau sufficient for the outgrowth of cell processes) with 20 μM inhibitors for 3 h before being harvested .
• Animal Research:
  Male mice (5–6 weeks old) were randomly assigned into five groups (n = 10). Group 1: received normal pellet diet (NPD); Group 2: received a HFD; Group 3–5 received HFD for 8 weeks followed by Indirubin-3'-monoxime (IMX) treatment (0.1, 0.2 and 0.4 mg/kg i.p, respectively) once daily for 1 week. IMX was dissolved in (2.5% v/v) DMSO in saline. The mice in NPD and HFD groups received an equivalent volume of vehicle (2.5% v/v DMSO in saline). The composition of HFD was similar as described by Srinivasan. Doses of IMX were selected based on the reports available in literature. Mice were kept under standard husbandry conditions (22 ± 1 C and 60% humidity) and maintained on a 12/12-h light/dark schedule with free access to food and water for 8 weeks. Body weight was recorded weekly throughout the experimental period .

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

CDK2/CyclinE, CDK1/CyclinB, CDK, CDK5/p25, Cyclin dependent kinase, Inhibitor, GSK-3β, GSK-3, GSK3, Glycogen synthase kinase 3, Glycogen synthase kinase-3, inhibit, Lipoxygenase, Indirubin-3'-oxime, Indirubin 3' monoxime, Indirubin-3'-monoxime, Indirubin3'monoxime, LOX

Compound Identifiers

PubChem CID

3707