KENPAULLONE

ChemicalBook > CAS DataBase List > 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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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:

INDIRUBIN-3'-MONOXIME Alsterpaullone NSC-41589 NSC-348884 3,4-Dichloro-N-(1-Methylbutyl)benza-Mide NSC 23766 TETRAHYDROCHLORIDE NSC697923 NSC5844 NSC632839hydrochloride NSC23005 Sodium Luteolin Indirubin RP107 NSC59984 (S)-CR8 KENPAULLONE (2-PHENYL-1H-INDOL-3-YL)-ACETALDEHYDE 2-(1H-Indol-2-yl)aniline

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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