Indirubin-3
INDIRUBIN-3'-MONOXIME
CAS: 160807-49-8
Molecular Formula: C16H11N3O2
Indirubin-3 - Names and Identifiers
| Name | INDIRUBIN-3'-MONOXIME |
| Synonyms | Indirubin-3 INDIRUBIN-3'-OXIME Indirubine-3'-oxime INDIRUBIN-3'-MONOXIME INDIRUBIN-3'-MONOOXIME 3-(hydroxyamino)-1H,2'H-2,3'-biindol-2'-one 3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-one 3-[1,3-DIHYDRO-3-(HYDROXYIMINO)-2H-INDOL-2-YLIDENE]-1,3-DIHYDRO-2H-INDOL-2-ONE |
| CAS | 160807-49-8 |
| InChI | InChI=1/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+ |
Indirubin-3 - Physico-chemical Properties
| Molecular Formula | C16H11N3O2 |
| Molar Mass | 277.28 |
| Density | 1.50 |
| Melting Point | 247-249°C |
| Boling Point | 532.2±50.0 °C(Predicted) |
| Water Solubility | DMSO: >10 mg/mL |
| Solubility | DMSO: >10mg/mL |
| Appearance | solid |
| Color | Dark red or brown |
| pKa | 8.66±0.20(Predicted) |
| Storage Condition | room temp |
| Stability | Light Sensitive |
| In vitro study | 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. 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. |
| In vivo study | 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. |
Indirubin-3 - Risk and Safety
| WGK Germany | 3 |
Indirubin-3 - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 3.607 ml | 18.033 ml | 36.065 ml |
| 5 mM | 0.721 ml | 3.607 ml | 7.213 ml |
| 10 mM | 0.361 ml | 1.803 ml | 3.607 ml |
| 5 mM | 0.072 ml | 0.361 ml | 0.721 ml |
Last Update：2024-01-02 23:10:35
Indirubin-3 - Reference Information
| Biological activity | Indirubin-3 '-monoxime (Indirubin-3'-oxime) is a selective CDK inhibitor. The IC50 for CDK1-cyclinB, CDK2-cyclinA, CDK2-cyclinE, CDK4-cyclinD1, and CDK5-p35 are 0.18 μM, 0.44 μM, 0.25 μM, 3.33 μM, 0.065 μM, respectively. Indirubin-3 '-monoxime is a direct and selective 5-lipoxygenase inhibitor with an IC50 of 7.8-10 µM. |
| Target | Value |
| CDK5-P35 (Cell-free assay) | 0.065 μM |
| CDK1-cyclinB (Cell-free assay) | 0.18 μM |
| CDK2-cyclinE (Cell-free assay) | 0.25 μM |
| CDK2-cyclinA (Cell-free assay) | 0.44 μM |
| CDK4-cyclinD1 (Cell-free assay) | 3.33 μM |
| use | A potent inhibitor of GSK-3β (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 (10 μ m). |
Last Update：2024-04-10 22:29:15
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