| Identification | More | [Name]
KENPAULLONE | [CAS]
142273-20-9 | [Synonyms]
CS-498
KenpauL
Kenpaullon
NSC-664704
KENPAULLONE
Kenpaullone>
9-BroMopaullone
NSC664704;NSC 664704
Kenpaullone Kenpaullone
NSC-664704(Kenpaullone)
Kenpaullone (NSC-664704)
NSC664704;NSC 664704;9-BROMOPAULLONE
Kenpaullone - CAS 142273-20-9 - Calbiochem
9-bromo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
9-BROMO-7,12-DIHYDRO-INDOLO[3,2-D][1]BENZAZEPIN-6(5H)-ONE
8-BROMO-7,12-DIHYDRO-INDOLO[3,2-D][1]-BENZAZEPIN-6(5H)-ONE
9-Bromo-7,12-dihydrobenzo[2,3]azepino[4,5-b]indol-6(5H)-one
Indolo[3,2-d][1]benzazepin-6(5H)-one, 9-bromo-7,12-dihydro-
9-Bromo-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one, NSC 664704
Kenpaullone
9-Bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one | [Molecular Formula]
C16H11BrN2O | [MDL Number]
MFCD02683595 | [Molecular Weight]
327.18 | [MOL File]
142273-20-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Tan Solid | [Melting point ]
>300°C (dec.) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: 18 mg/mL, clear, yellow
| [form ]
Yellow-brown solid | [color ]
yellow
| [Usage]
The paullones are a novel class of kinase inhibitors, initially identified as CDK inhibitors. Kenpaullone has been found to be a useful GSK-3?inhibitor (IC50=23nM). | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. | [InChIKey]
QQUXFYAWXPMDOE-UHFFFAOYSA-N | [CAS DataBase Reference]
142273-20-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
2933.79.1500 |
| Hazard Information | Back Directory | [Description]
Kenpaullone (142273-20-9) inhibits GSK-3β (IC50=0.23 μM) as well as several cyclin-dependent kinases (CDKs), IC50=0.4, 0.68 and 0.85 μM for cdk1, cdk2 and cdk5 respectively.1-3 Induces pluripotent stem cells from somatic cells4 and increases direct neural conversion of human fibroblasts5 when used with other small molecules. Inhibits Kruppel-Like Factor 4 (KLF4) reducing autoimmune arthritis in the collagen-induced arthritis mouse model.6 | [Chemical Properties]
Tan Solid | [Uses]
The paullones are a novel class of kinase inhibitors, initially identified as CDK inhibitors. Kenpaullone has been found to be a useful GSK-3?inhibitor (IC50=23nM). | [Uses]
The paullones are a novel class of kinase inhibitors, initially identified as CDK inhibitors. Kenpaullone has been found to be a useful GSK-3? inhibitor (IC50=23nM). | [Definition]
ChEBI: Kenpaullone is an indolobenzazepine that is paullone in which the hydrogen at position 9 is replaced by a bromo substituent. It is an ATP-competitive inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase 3beta (GSK3beta). It has a role as a geroprotector, an EC 2.7.11.26 (tau-protein kinase) inhibitor, a cardioprotective agent and an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor. It is an indolobenzazepine, a lactam and an organobromine compound. It is functionally related to a paullone. | [General Description]
A potent, cell-permeable, and reversible inhibitor of glycogen synthase kinase-3β (IC50 = 230 nM), Lck (IC50 = 470 nM), and cyclin-dependent kinases (Cdks). Inhibits Cdk1/cyclin B (IC50 = 400 nM), Cdk2/cyclin A (IC50 = 680 nM), Cdk2/cyclin E (IC50 = 7.5 μM), and Cdk5/p25 (IC50 = 850 nM). Also inhibits other kinases such as c-Src (IC50 = 15 μM), casein kinase II (IC50 = 20 μM), ERK1 (IC50 = 20 μM), and ERK2 (IC50 = 9 μM). Inhibition is competitive with respect to ATP binding. | [Biological Activity]
Potent inhibitor of CDK1/cyclin B and GSK-3 β (IC 50 values are 0.4 and 0.23 μ M respectively). Also inhibits CDK2/cyclin A, CDK2/cyclin E and CDK5/cyclin/p35 (IC 50 values are 0.68, 7.5 and 0.85 μ M respectively). Selective over c-src (IC 50 = 15 μ M), casein kinase 2 (IC 50 = 20 μ M), ERK1 (IC 50 = 20 μ M), ERK2 (IC 50 = 9 μ M) and a range of other protein kinases (IC 50 values > 35 μ M). Generates induced pluripotent stem cells (iPSCs) from somatic cells when used in combination with reprogramming factors; can replace Klf4. | [Biochem/physiol Actions]
Kenpaullone is also an inhibitor of glycogen synthase kinase 3β (GSK3β).?It also inhibits cyclin-dependent kinase 1 (CDK1/cyclin B), CDK2/cyclin A, CDK2/cyclin E, and CDK5/p25, majorly by competitive inhibition of adenosine triphosphate (ATP) binding. | [storage]
Store at RT | [References]
Zaharevitz et al. (1999), Discovery and initial characterization of the paullones, a novel class of small-molecule inhibitors of cyclin-dependent kinases; Cancer Res. 59 2566
Schultz et al. (1999) Paullones, a series of cyclin-dependent kinase inhibitor: synthesis, evaluation of CDK1/cyclin B inhibition, and in vitro antitumor activity; J.Med.Chem. 42 2909
Bain et al. (2003), The specificities of protein kinase inhibitors: an update; J. 371(Pt. 1) 199
Lyssiotis et al. (2009) Reprogramming of murine fibroblasts to induced pluripotent stem cells with chemical complementation of Klf4; Natl. Acad. Sci. USA 106 8912
Pfisterer et al. (2016), Small molecules increase direct neural conversion of human fibroblasts; Rep. 6 38290
Choi et al. (2018), Kruppel-Like Factor 4 Positively Regulates Autoimmune Arthritis in Mouse Models and Rheumatoid Arthritis in Patients via Modulating Cell Survival and Inflammation Factors of Fibroblast-Like Synoviocyte; Immunol. 9 1339 |
|
|