| Identification | Back Directory | [Name]
1-AZAKENPAULLONE | [CAS]
676596-65-9 | [Synonyms]
1-AZAKENPAULLONE
InSolution? 1-Azakenpaullone
9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one
Pyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one, 9-broMo-7,12-dihydro-
1-Azakenpaullone
9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C15H10BrN3O | [MDL Number]
MFCD09037522 | [MOL File]
676596-65-9.mol | [Molecular Weight]
328.16 |
| Chemical Properties | Back Directory | [Appearance]
Tan Solid | [Melting point ]
>290°C (dec.) | [Boiling point ]
648.8±50.0 °C(Predicted) | [density ]
1.655±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO: >10mg/mL | [form ]
Tan solid | [pka]
13.36±0.20(Predicted) | [color ]
gray-brown | [InChI]
InChI=1S/C15H10BrN3O/c16-8-3-4-11-9(6-8)10-7-13(20)18-12-2-1-5-17-15(12)14(10)19-11/h1-6,19H,7H2,(H,18,20) | [InChIKey]
NTSBZVCEIVPKBJ-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(Br)C=C2)C2CC(=O)NC3=CC=CN=C3C1=2 |
| Hazard Information | Back Directory | [Chemical Properties]
Tan Solid | [Uses]
A selective inhibitor of glycogen synthase kinase-3β. | [Definition]
ChEBI: 1-azakenpaullone is an organic heterotetracyclic compound that is 7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indole substituted at positions 6 and 9 by oxo and bromo groups respectively. It has a role as an EC 2.7.11.26 (tau-protein kinase) inhibitor and a Wnt signalling activator. It is an organic heterotetracyclic compound, an organonitrogen heterocyclic compound, a lactam and an organobromine compound. | [General Description]
A Kenpaullone (>Cat. No. 422000) analog that acts as a potent and ATP-competitive inhibitor of GSK-3β (IC50 = 18 nM). Displays over 100-fold greater selectivity over Cdk1/cyclin B and Cdk5/p25 (IC50 = 2.0 μM and 4.2 μM, respectively). The solid form of this compound (Cat. No. 191500) is also available. | [Biological Activity]
1-azakenpaullone is a selective and cell-permeable inhibitor of glycogen synthase kinase-3β (gsk-3β) with ic50 value of 18nm [1, 2].1-azakenpaullone is a kenpaullone derivative with a modified heterocyclic basic structure. it shows potent inhibitory activity against gsk-3β over cdk1/cyclin b and cdk5/p25. the ic50 values for cdk1/cyclin b, cdk5/p25 and gsk-3β are 2μm, 4.2μm and 18nm, respectively. as an inhibitor of gsk-3β, 1-azakenpaullone is developed as potential antidiabetic drug. 1-azakenpaullone is found to protect rat insulinoma cell line ins-1e cells from glucolipotoxicity and stimulate cell proliferation. besides that, 1-azakenpaullone promotes the replication of beta cells in isolated rat islets at concentration of 1μm. in addition, 1-azakenpaullone is reported to have effect in changing cardiac myocyte morphology. it increases cell area primarily through the elongation of the cells [1, 2 and 3]. | [Biochem/physiol Actions]
Cell permeable: yes | [Enzyme inhibitor]
This cell-permeable protein kinase inhibitor (FW = 328.17 g/mol; CAS 676596-65-9: Solubility: 66 mg/mL DMSO; <1 mg/mL H2O), also named 9-bromo-7,12-dihydro-pyrido[3,2’:2,3]azepino[4,5-b]indol-6(5H)-one, selectively and potently targets glycogen synthase kinase 3β, or GSK3β (IC50 = 18 nM) with 100x less inhibitory action against cyclin-dependent kinases (CDKs). 1-Azakenpaullone has become a gold standard for GSK3 inhibition. | [target]
GSK-3β | [storage]
+4°C | [References]
[1] kunick c, lauenroth k, leost m, et al. 1-azakenpaullone is a selective inhibitor of glycogen synthase kinase-3β. bioorganic & medicinal chemistry letters, 2004, 14(2): 413-416.
[2] mussmann r, geese m, harder f, et al. inhibition of gsk3 promotes replication and survival of pancreatic beta cells. journal of biological chemistry, 2007, 282(16): 12030-12037.
[3] markou t, cullingford t e, giraldo a, et al. glycogen synthase kinases 3α and 3β in cardiac myocytes: regulation and consequences of their inhibition. cellular signalling, 2008, 20(1): 206-218. |
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