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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
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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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
HS Code 
2933.79.1500
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
K3888
Product name
Kenpaullone
Purity
≥98%
Packaging
1mg
Price
$152
Updated
2024/03/01
Sigma-Aldrich
Product number
K3888
Product name
Kenpaullone
Purity
≥98%
Packaging
5mg
Price
$543
Updated
2024/03/01
Sigma-Aldrich
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
$159
Updated
2024/03/01
TCI Chemical
Product number
K0052
Product name
Kenpaullone
Purity
>97.0%(HPLC)
Packaging
10mg
Price
$161
Updated
2024/03/01
TCI Chemical
Product number
K0052
Product name
Kenpaullone
Purity
>97.0%(HPLC)
Packaging
50mg
Price
$570
Updated
2024/03/01
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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.

storage

Room temperature

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

KENPAULLONE Preparation Products And Raw materials

Raw materials

Preparation Products

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KENPAULLONE Suppliers

Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
China DongFan Chemical Co.,LTD
Tel
86-0571-85151182
Fax
86-0571-85151182
Country
China
ProdList
5691
Advantage
66
ChemCell Biomedicine Co.,Ltd.
Tel
020-13556033878 2965585218 13556033878
Fax
0086-0757-85406358
Email
chemcell@hotmail.com
Country
China
ProdList
369
Advantage
52
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
Country
China
ProdList
4727
Advantage
58
Shanghai Topbiochem Technology Co., Ltd
Tel
021-58170097
Email
info@topbiochem.com
Country
China
ProdList
9458
Advantage
58
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View Lastest Price from KENPAULLONE manufacturers

Career Henan Chemical Co
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

142273-20-9, KENPAULLONERelated Search:


  • 9-Bromo-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one, NSC 664704
  • 9-BroMopaullone
  • Kenpaullon
  • 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
  • KENPAULLONE
  • NSC-664704
  • Kenpaullone 9-Bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
  • 9-bromo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
  • 9-Bromo-7,12-dihydrobenzo[2,3]azepino[4,5-b]indol-6(5H)-one
  • Kenpaullone (NSC-664704)
  • NSC664704;NSC 664704
  • Kenpaullone - CAS 142273-20-9 - Calbiochem
  • CS-498
  • NSC-664704(Kenpaullone)
  • NSC664704;NSC 664704;9-BROMOPAULLONE
  • Kenpaullone Kenpaullone
  • Kenpaullone&gt
  • KenpauL
  • Indolo[3,2-d][1]benzazepin-6(5H)-one, 9-bromo-7,12-dihydro-
  • 142273-20-9
  • 142273-29-9
  • C16H11BrN2O
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