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| | 1-AZAKENPAULLONE Basic information |
| Product Name: | 1-AZAKENPAULLONE | | Synonyms: | 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-;InSolution? 1-Azakenpaullone;1-Azakenpaullone
9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one;InSolution 1-Azakenpaullone - CAS 676596-65-9 - Calbiochem;1-Azakenpaullone - CAS 676596-65-9 - Calbiochem;azakenpaullone | | CAS: | 676596-65-9 | | MF: | C15H10BrN3O | | MW: | 328.16 | | EINECS: | 200-258-5 | | Product Categories: | All Inhibitors;Inhibitors;Protein Kinase Inhibitors and Activators | | Mol File: | 676596-65-9.mol |  |
| | 1-AZAKENPAULLONE Chemical Properties |
| Melting point | >290°C (dec.) | | Boiling point | 648.8±50.0 °C(Predicted) | | density | 1.655±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | DMSO: >10mg/mL | | pka | 13.36±0.20(Predicted) | | form | Tan solid | | 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 |
| | 1-AZAKENPAULLONE Usage And Synthesis |
| 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. |
| | 1-AZAKENPAULLONE Preparation Products And Raw materials |
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