ChemicalBook > CAS DataBase List > Alsterpaullone

Alsterpaullone

Product Name
Alsterpaullone
CAS No.
237430-03-4
Chemical Name
Alsterpaullone
Synonyms
NSC 705701;ALSTERPAULLONE;9-Nitropaullone;Alsteropaullone;Alsterpaullone (9-Nitropaullone;ALSTERPAULLONE (9-NITROPAULLONE;NSC 705701);Alsterpaullone - CAS 237430-03-4 - Calbiochem;7,12-Dihydro-9-nitroindolo[3,2-d][1]benzazepin-6(5H)-one;9-NITRO-7,12-DIHYDROINDOLO-[3,2-D][1]BENZAZEPIN-6(5)-ONE;9-nitro-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
CBNumber
CB0778141
Molecular Formula
C16H11N3O3
Formula Weight
293.28
MOL File
237430-03-4.mol
More
Less

Alsterpaullone Property

Melting point:
>330℃
Boiling point:
651.5±45.0 °C(Predicted)
Density 
1.461±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble
form 
powder
pka
14.18±0.20(Predicted)
color 
brown
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
More
Less

Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A4847
Product name
Alsterpaullone
Purity
≥98% (HPLC), powder
Packaging
1mg
Price
$178
Updated
2024/03/01
Sigma-Aldrich
Product number
126870
Product name
Alsterpaullone
Packaging
1mg
Price
$159
Updated
2024/03/01
Cayman Chemical
Product number
14428
Product name
Alsterpaullone
Purity
≥98%
Packaging
1mg
Price
$68
Updated
2024/03/01
Cayman Chemical
Product number
14428
Product name
Alsterpaullone
Purity
≥98%
Packaging
5mg
Price
$302
Updated
2024/03/01
Tocris
Product number
6400
Product name
Alsterpaullone
Purity
≥98%(HPLC)
Packaging
10
Price
$212
Updated
2021/12/16
More
Less

Alsterpaullone Chemical Properties,Usage,Production

Description

Alsterpaullone (237430-03-4) is a potent and selective inhibitor of GSK-3β and CDK5/p25. Potent inhibitor of CDK1/cyclin B (IC50 = 35 nM).1?Alsterpaullone induces apoptosis2 and inhibits angiogenesis3.

Uses

Alsterpaullone is a derivative of kenpaullone , an ATP-competitive inhibitor of several cyclin-dependent kinases (CDKs) as well as glycogen synthase kinase 3β (GSK3β). With slightly improved potency over kenpaullone, alsterpaullone selectively inhibits Cdk1/cyclin B, Cdk2/cyclin A, Cdk2/cyclin E, Cdk5/p25, and GSK3α/β with IC50 values of 35, 15, 200, 40, and 4 nM, respectively. Alsterpaullone has been used to inhibit the cytosolic degradation of β-catenin to alter the canonical Wnt signaling pathway in primary axis patterning, to reduce tau phosphorylation in an effort to modify neuropathological events associated with Alzheimer’s disease, and to alter cell proliferation or protein expression in various diseases.

Uses

Alsterpaullone has been used to stabilize β-catenin.

Uses

Alsterpaullone is a potent glycogen synthase kinase-3 inhibitor and a potential therapeutic agents for treatment of Parkinson disease.

Definition

ChEBI: Alsterpaullone is an organic heterotetracyclic compound that is 1,3-dihydro-2H-1-benzazepin-2-one which shares its 4-5 bond with the 3-2 bond of 5-nitro-1H-indole. It has a role as an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, an EC 2.7.11.26 (tau-protein kinase) inhibitor, an antineoplastic agent, an apoptosis inducer and an anti-HIV-1 agent. It is a C-nitro compound, an organic heterotetracyclic compound and a member of caprolactams. It derives from a paullone.

Biochem/physiol Actions

Alsterpaullone (ALP) is a cyclin-dependent kinase (CDK) inhibitor. It is considered as a therapeutic agent for group 3 medulloblastomas. Alsterpaullone modulates the progression of cell cycle.?It can arrest cell cycle and stimulate the apoptosis of cancer cells by activating caspase-9 through perturbation of mitochondrial membrane potential.

storage

+4°C

References

1) Bain et al. (2003), The specificities of protein kinase inhibitors: an update; Biochem. J., 371 199 2) Lahusen et al. (2003), Alsterpaullone, a novel cyclin-dependent kinase inhibitor, induces apoptosis by activation of caspase-9 due to perturbation in mitochondrial membrane potential; Mol. Carcinog., 36 183 3) Zahler et al. (2010), Anti-angiogenic potential of small molecular inhibitors of cyclin dependent kinases in vitro; Angiogenesis, 13 239

Alsterpaullone Preparation Products And Raw materials

Raw materials

Preparation Products

237430-03-4, AlsterpaulloneRelated Search:


  • ALSTERPAULLONE
  • 9-NITRO-7,12-DIHYDROINDOLO-[3,2-D][1]BENZAZEPIN-6(5H)-ONE
  • 9-NITRO-7,12-DIHYDROINDOLO-[3,2-D][1]BENZAZEPIN-6(5)-ONE
  • 9-nitro-7,12-dihydrobenzo[2,3]azepino[4,5-b]indol-6(5H)-one
  • 9-Nitropaullone
  • NSC 705701
  • Alsterpaullone (9-Nitropaullone
  • ALSTERPAULLONE (9-NITROPAULLONE;NSC 705701)
  • Alsteropaullone
  • Alsterpaullone - CAS 237430-03-4 - Calbiochem
  • 7,12-Dihydro-9-nitroindolo[3,2-d][1]benzazepin-6(5H)-one
  • Indolo[3,2-d][1]benzazepin-6(5H)-one, 7,12-dihydro-9-nitro-
  • 9-nitro-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
  • CDK5,GSK-3,p35,NSC-705701,9-Nitropaullone,NSC705701,ALSTERPAULLONE,Glycogen synthase kinase-3,cyclin E,Glycogen synthase kinase 3,Cyclin dependent kinase,inhibit,NSC 705701,antitumor,CDK2,cyclin A,cyclin B,Inhibitor,CDK,Apoptosis,CDK1,neurodegenerative
  • 237430-03-4
  • Kinase/Phosphatase Biology
  • Serine/Threonine Kinase Inhibitors
  • Cyclin-Dependent Kinase (CDK)
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Caspases/Apoptosis