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142273-20-9

142273-20-9 structure
142273-20-9 structure
  • Name: Kenpaullone
  • Chemical Name: Kenpaullone
  • CAS Number: 142273-20-9
  • Molecular Formula: C16H11BrN2O
  • Molecular Weight: 327.175
  • Catalog: Signaling Pathways Cell Cycle/DNA Damage CDK
  • Create Date: 2018-09-05 13:19:56
  • Modify Date: 2024-01-02 21:42:31
  • Kenpaullone is a potent inhibitor of CDK1/cyclin B and GSK-3β, with IC50s of 0.4 μM and 23 nM, and also inhibits CDK2/cyclin A, CDK2/cyclin E, and CDK5/p25 with IC50s of 0.68 μM, 7.5 μM, 0.85 μM, respectively.

Name Kenpaullone
Synonyms 9-Bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
Indolo[3,2-d][1]benzazepin-6(5H)-one, 9-bromo-7,12-dihydro-
9-bromo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
Kenpaullone
MFCD02683595
9-Bromo-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one
NSC-664704
Description Kenpaullone is a potent inhibitor of CDK1/cyclin B and GSK-3β, with IC50s of 0.4 μM and 23 nM, and also inhibits CDK2/cyclin A, CDK2/cyclin E, and CDK5/p25 with IC50s of 0.68 μM, 7.5 μM, 0.85 μM, respectively.
Related Catalog
Target

Cdk1/cyclin B:0.4 μM (IC50)

cdk2/cyclin A:0.68 μM (IC50)

CDK5/p35:0.85 μM (IC50)

CDK2/cyclinE:7.5 μM (IC50)

GSK-3β:0.023 μM (IC50)

erk1:20 μM (IC50)

erk2:9 μM (IC50)

c-raf:38 μM (IC50)

In Vitro Kenpaullone shows much less effect on c-src (IC50, 15 μM), casein kinase 2 (IC50, 20 μM), erk 1 (IC50, 20 μM), and erk 2 (IC50, 9 μM). Kenpaullone acts by competitive inhibition of ATP binding, and the apparent Ki is 2.5 μM. Kenpaullone can inhibit the growth of tumor cells in culture (mean GI50, 43 μM) and causes altered cell cycle progression most clearly revealed under conditions of recovery from serum starvation[1]. Kenpaullone demonstrates a wide range of biological utility, extending from maintenance of pancreatic β cell survival and proliferation to the induction of apoptosis in cancer cells[2].
Kinase Assay The kinase assay is run for 10 min at 30°C with 1 mg/mL histone H1, in the presence of 15 μM [g-32P]ATP (3000 Ci/μmol; 1 mCi/mL) in a final volume of 30 ml. Purification and assays or inhibition of other kinases are performed. In kinetic experiments, the histone H1 concentration is lowered to 3.5 mg/mL; the ATP concentration ranged from 50 to 400 μM, and the kenpaullone concentration ranges from 1 to 4 μM.
References

[1]. Zaharevitz DW, et al. Discovery and initial characterization of the paullones, a novel class of small-molecule inhibitors of cyclin-dependent kinases. Cancer Res. 1999 Jun 1;59(11):2566-9.

[2]. Lyssiotis CA, et al. Reprogramming of murine fibroblasts to induced pluripotent stem cells with chemical complementation of Klf4. Proc Natl Acad Sci U S A. 2009 Jun 2;106(22):8912-7.

Density 1.6±0.1 g/cm3
Boiling Point 613.0±45.0 °C at 760 mmHg
Melting Point >300ºC (dec.)
Molecular Formula C16H11BrN2O
Molecular Weight 327.175
Flash Point 324.5±28.7 °C
Exact Mass 326.005463
PSA 44.89000
LogP 4.02
Vapour Pressure 0.0±1.8 mmHg at 25°C
Index of Refraction 1.730
Storage condition 2-8°C
Water Solubility DMSO: 18 mg/mL, clear, yellow
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi: Irritant;
Risk Phrases R36/37/38
Safety Phrases 26-36
RIDADR NONH for all modes of transport
WGK Germany 3