Indirubin-3'-monoxime
-oxime · -monoxime · Indirubin-3 · Indirubin-3′INDIRUBIN-3'-OXIME · Indirubine-3'-oxime · Indirubin-3'-monoxime · INDIRUBIN-3’-MONOOXIME · Indirubin-3''-monoxime, 10 mM in DMSO
Identifikatoren & physikalische Daten
| CAS No. | 160807-49-8 |
|---|---|
| Summenformel | C16H11N3O2 |
| Durchschnittliche Molmasse | 277,28 g/mol |
| Monoisotopische Masse | 277,0851266 g/mol |
| SMILES | O=Nc1c(-c2c(O)[nH]c3ccccc23)[nH]c2ccccc12 |
| InChIKey | FQCPPVRJPILDIK-UHFFFAOYSA-N |
| PubChem CID | 3707 |
| ChEMBL | CHEMBL126077 |
| ChEBI | CHEBI:43645 |
| DTXSID | DTXSID90416111 |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 81,2 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 405 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Schmelzpunkt | 247-249°C |
| Siedepunkt | 532.2±50.0 °C(Predicted) |
| Dichte | 1.50 |
| Lagerbedingungen | room temp |
| Löslichkeit | DMSO: >10 mg/mL |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | 8.66±0.20(Predicted) |
| Farbe | Dark red or brown |
| Stabilität | Light Sensitive |
| InChIKey | HBDSHCUSXQATPO-UHFFFAOYSA-N |
| CAS Datenbank | 160807-49-8 |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Indirubin-3’-oxime is a potent inhibitor of glycogen synthase kinase 3β (GSK3β; IC50 = 22 nM). As GSK3β phosphorylates tau protein, indirubin-3’-oxime prevents tau phosphorylation both in vitro and in vivo at Alzheimer’s disease-relevant sites. 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.
Verwenden
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).