KENPAULLONE
- Product Name
- KENPAULLONE
- CAS No.
- 142273-20-9
- Chemical Name
- KENPAULLONE
- Synonyms
- CS-498;KenpauL;Kenpaullon;NSC-664704;KENPAULLONE;Kenpaullone>9-BroMopaullone;NSC664704;NSC 664704;NSC-664704(Kenpaullone);Kenpaullone Kenpaullone
- CBNumber
- CB1449240
- Molecular Formula
- C16H11BrN2O
- Formula Weight
- 327.18
- MOL File
- 142273-20-9.mol
KENPAULLONE Property
- Melting point:
- >300°C (dec.)
- Boiling point:
- 613.0±45.0 °C(Predicted)
- Density
- 1.596±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- DMSO: 18 mg/mL, clear, yellow
- form
- Yellow-brown solid
- pka
- 14.29±0.20(Predicted)
- color
- yellow
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- K3888
- Product name
- Kenpaullone
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $156
- Updated
- 2025/07/31
- Product number
- K3888
- Product name
- Kenpaullone
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $558
- Updated
- 2025/07/31
- Product number
- 422000
- Product name
- Kenpaullone - CAS 142273-20-9 - Calbiochem
- Purity
- A potent, cell-permeable, and reversible inhibitor of glycogen synthase kinase-3β (IC?? = 230 nM), Lck (IC?? = 470 nM), and cyclin-dependent kinases (Cdks).
- Packaging
- 1MG
- Price
- $139
- Updated
- 2025/07/31
- Product number
- K0052
- Product name
- Kenpaullone
- Purity
- >97.0%(HPLC)
- Packaging
- 10mg
- Price
- $145
- Updated
- 2025/07/31
- Product number
- K0052
- Product name
- Kenpaullone
- Purity
- >97.0%(HPLC)
- Packaging
- 50mg
- Price
- $513
- Updated
- 2025/07/31
KENPAULLONE Chemical Properties,Usage,Production
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
Kenpaullone has been used:
- as a glycogen synthase kinase 3 (GSK3)/ cyclin-dependent kinase (CDK) inhibitor to study its effects on human neural progenitor cell lines
- as an inhibitor of Krupple-like factor 4 (KLF4) in Gs-coupled designer GPCR (Gs DREADD= GsD) Agouti-related peptide (GsD-AgRP) mice
- as a GSK3/CDK inhibitor to study its effects on the sea urchin embryo development
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.
Synthesis
16511-38-9
589-21-9
142273-20-9
A suspension was formed in glacial acetic acid (10 ml) with 3,4-dihydrobenzo[b]azepine-2,5-dione (1.05 g, 6 mmol) and p-bromophenylhydrazine (7 mmol). The mixture was stirred and reacted at 70°C for 1 hour. After completion of the reaction, it was cooled to room temperature and 0.5 ml of concentrated hydrochloric acid was added to continue stirring. Subsequently, H2SO4 was added at 70°C and the reaction was kept for 1 hour. After the reaction mixture was cooled, it was poured into 50 ml of 10% sodium acetate solution and precipitated. The yellow crystalline product was collected by diafiltration. The product was 9-bromo-7,12-dihydrobenzo[2,3]azepino[4,5-b]indol-6(5H)-one in 58% yield and melting point >330°C (1,4-dioxane). Molecular formula: C16H11BrN2O (327.2).IR spectrum showed: 3220 cm-1 (NH stretching vibration); 1640 cm-1 (C=O stretching vibration).1H NMR (δ, ppm): 11.75 (s, 1H, NH), 10.05 (s, 1H, NH), 7.89 (d, 1H, J = 1.5Hz, C-8- H), 7.74 (bd, 1H, J = 7.5 Hz, Ar-H), 7.41-7.34 (m, 2H, Ar-H), 7.30-7.21 (m, 3H, Ar-H), 3.50 (s, 2H, CH2).
storage
Room temperature
References
[1] D W ZAHAREVITZ. Discovery and initial characterization of the paullones, a novel class of small-molecule inhibitors of cyclin-dependent kinases.[J]. Cancer research, 1999, 59 11: 2566-2569.
[2] CHRISTIANE SCHULTZ. Paullones, a Series of Cyclin-Dependent Kinase Inhibitors: Synthesis, Evaluation of CDK1/Cyclin B Inhibition, and in Vitro Antitumor Activity[J]. Journal of Medicinal Chemistry, 1999, 42 15: 2909-2919. DOI:10.1021/jm9900570
[3] JENNY BAIN. The specificities of protein kinase inhibitors: an update.[J]. Biochemical Journal, 2003, 371 Pt 1: 199-204. DOI:10.1042/bj20021535
[4] COSTAS A LYSSIOTIS. Reprogramming of murine fibroblasts to induced pluripotent stem cells with chemical complementation of Klf4.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2009, 106 22: 8912-8917. DOI:10.1073/pnas.0903860106
[5] U. PFISTERER. Small molecules increase direct neural conversion of human fibroblasts[J]. Scientific Reports, 2016, 6 1. DOI:10.1038/srep38290
[6] SEUNGJIN CHOI. 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.[J]. ACS Applied Materials & Interfaces, 2018: 1339. DOI:10.3389/fimmu.2018.01339
KENPAULLONE Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from KENPAULLONE manufacturers
- Product
- KENPAULLONE 142273-20-9
- Price
- US $1.00/g
- Min. Order
- 100g
- Purity
- 98%min
- Supply Ability
- G/KG/T
- Release date
- 2019-12-20