| Identification | Back Directory | [Name]
INDIRUBIN-3-MONOXIME | [CAS]
667463-82-3 | [Synonyms]
(2Z,3E)-3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-one | [Molecular Formula]
C16H11N3O2 | [MDL Number]
MFCD02683594 | [MOL File]
667463-82-3.mol | [Molecular Weight]
277.28 |
| Chemical Properties | Back Directory | [Boiling point ]
532.2±50.0 °C(Predicted) | [density ]
1.50±0.1 g/cm3(Predicted) | [form ]
Solid | [pka]
10.69±0.20(Predicted) | [color ]
Brown to red |
| Hazard Information | Back Directory | [Uses]
Indirubin-3′-oxime (IDR3O), a synthetic derivative of indirubin, is a potent inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase 3β (GSK3β). Indirubin-3′-oxime directly inhibits the activity of all three isoforms of JNK (JNK1, JNK2, and JNK3), with IC50s of 0.8 μM, 1.4 μM, and 1.0 μM, respectively. Indirubin-3′-oxime can enhance height growth via activation of Wnt/β-catenin signaling in chondrocytes[1][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. | [in vivo]
Indirubin-3′-oxime (0.05 or 0.5?mg/kg; i.p.; daily for 2 or 10 weeks) enhances tibial longitudinal growth in mice without adverse changes in bone thickness parameters[3]. | Animal Model: | Three-week-old C57BL/6 mice[3] | | Dosage: | 0.05 or 0.5?mg/kg | | Administration: | I.p.; daily for 2 or 10 weeks | | Result: | The tibial length of mice increased in a dose-dependent manner.
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| [IC 50]
JNK1: 0.8 μM (IC50); JNK2: 1.4 μM (IC50); JNK3: 1 μM (IC50); GSK-3β; CDK | [References]
[1] Xie Y, et al. Indirubin-3'-oxime inhibits c-Jun NH2-terminal kinase: anti-apoptotic effect in cerebellar granule neurons. Neurosci Lett. 2004;367(3):355-359. DOI:10.1016/j.neulet.2004.06.044
[2] Hu S, et al. Indirubin-3-Oxime Effectively Prevents 6OHDA-Induced Neurotoxicity in PC12 Cells via Activating MEF2D Through the Inhibition of GSK3β. J Mol Neurosci. 2015;57(4):561-570. DOI:10.1007/s12031-015-0638-y
[3] Choi S, et al. Indirubin-3'-oxime stimulates chondrocyte maturation and longitudinal bone growth via activation of the Wnt/β-catenin pathway. Exp Mol Med. 2019;51(9):1-10. Published 2019 Sep 12. DOI:10.1038/s12276-019-0306-3 |
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