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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
Molecular Weight:
293.28
MDL Number:
MFCD02683579
MOL File:
237430-03-4.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

Alsterpaullone Properties

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.

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
NFPA 704
0
2 0

Alsterpaullone price More Price(21)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A4847 Alsterpaullone ≥98% (HPLC), powder 237430-03-4 1mg $178 2024-03-01 Buy
Sigma-Aldrich 126870 Alsterpaullone 237430-03-4 1mg $159 2024-03-01 Buy
Cayman Chemical 14428 Alsterpaullone ≥98% 237430-03-4 1mg $68 2024-03-01 Buy
Cayman Chemical 14428 Alsterpaullone ≥98% 237430-03-4 5mg $302 2024-03-01 Buy
Tocris 6400 Alsterpaullone ≥98%(HPLC) 237430-03-4 10 $212 2021-12-16 Buy
Product number Packaging Price Buy
A4847 1mg $178 Buy
126870 1mg $159 Buy
14428 1mg $68 Buy
14428 5mg $302 Buy
6400 10 $212 Buy

Alsterpaullone Chemical Properties,Uses,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

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Alsterpaullone Spectrum

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