[CAS NO. 160807-49-8] Indirubin-3'-monoxime
PRODUCTS SPECIFICATIONS [160807-49-8]
DESCRIPTION [160807-49-8]
Overview
| MDL | MFCD02683594 |
|---|---|
| Molecular Weight | 277.28 |
| Molecular Formula | C16H11N3O2 |
| SMILES | O=C1NC2=C(C=CC=C2)/C1=C3NC4=C(C=CC=C4)C\3=N/O |
2 Publications Citing Use of MCE
Summary
Indirubin-3'-monoxime is a potent GSK-3β inhibitor, and weakly inhibits 5-Lipoxygenase , with IC 50 s of 22 nM and 7.8-10 µM, respectively; Indirubin-3'-monoxime also shows inhibitory activities against CDK5/p25 and CDK1/cyclin B, with IC 50 s of 100 and 180 nM.
IC50 & Target
|
GSK-3β 22 nM (IC 50 ) |
CDK5/p25 100 nM (IC 50 ) |
CDK1/cyclin B 180 nM (IC 50 ) |
5-LOX 7.8-10 μM (IC 50 ) |
In Vitro
Indirubin-3'-monoxime inhibits GSK-3β by competing with ATP, with K i of 0.85 μM, and K m of 110 μM. Indirubin-3'-monoxime also inhibits tau phosphorylation by GSK-3β, with an IC 50 value of around 100 nM. Indirubin-3'-monoxime completely inhibits the phosphorylation of the AT100 epitope [1] . Indirubin-3'-monoxime inhibits vascular smooth muscle cell (VSMC) proliferation with IC 50 of ∼2 µM. Indirubin-3'-monoxime blunts migration of VSMC stimulated with the PDGF. Indirubin-3'-monoxime interferes with the migratory response in VSMC, and also suppresses the production of pro-migratory LT in monocytes. Moreover, Indirubin-3'-monoxime inhibits 5-lipoxygenase (5-LO) product synthesis in monocytes and neutrophils, with the same potency (IC 50 =5.0±1.1 and 3.7±1.2 µM, respectively). Indirubin-3'-monoxime is an inhibitor of 5-LO, with IC 50 of 7.8-10 µM in cell-free assay [3] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Indirubin-3'-monoxime (0.1, 0.2 and 0.4 mg/kg, i.p) dose dependently reverses the cognitive impairment and combats the elevated oxidative stress markers in HFD fed mice. Indirubin-3'-monoxime also dose dependently lowers the serum glucose, TGs, TC and insulin levels, and improves the β-cell functioning in HFD fed mice. Moreover, Indirubin-3'-monoxime treatment significantly decreases HOMA-IR levels compared to HFD group. Indirubin-3'-monoxime (0.4 mg/kg) significantly attenuates the increased EL in the HFD group [2] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| 4°C | 2 years | |
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
DMSO : ≥ 37 mg/mL ( 133.44 mM )
* "≥" means soluble, but saturation unknown.
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 3.6065 mL | 18.0323 mL | 36.0646 mL |
| 5 mM | 0.7213 mL | 3.6065 mL | 7.2129 mL |
| 10 mM | 0.3606 mL | 1.8032 mL | 3.6065 mL |
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1.
References
- [1] Leclerc S, et al. 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. 2001 Jan 5;2
- [2] Sharma S, et al. Neuroprotective role of Indirubin-3'-monoxime, a GSKβ inhibitor in high fat diet induced cognitive impairment in mice. Biochem Biophys Res Commun. 2014 Oct 3;452(4):1009-15.
- [3] Blazevic T, et al. Indirubin-3'-monoxime exerts a dual mode of inhibition towards leukotriene-mediated vascular smooth muscle cell migration. Cardiovasc Res. 2014 Mar 1;101(3):522-32.
- [4] Cao Z, et al. Indirubin Derivatives as Dual Inhibitors Targeting Cyclin-Dependent Kinase and Histone Deacetylase for Treating Cancer [published online ahead of print, 2021 Oct 8]. J Med Chem. 2021;10.1021/acs.jmedchem.1c01311.
