676596-65-9 Usage
Chemical Properties
Tan Solid
Uses
A selective inhibitor of glycogen synthase kinase-3β.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 676596-65-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 6,7,6,5,9 and 6 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 676596-65:
(8*6)+(7*7)+(6*6)+(5*5)+(4*9)+(3*6)+(2*6)+(1*5)=229
229 % 10 = 9
So 676596-65-9 is a valid CAS Registry Number.
