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Merck

A4847

Alsterpaullone

≥98% (HPLC), GSK-3β and CDK5/p25 inhibitor, powder

Synonyme(s) :

9-Nitro-7,12-dihydroindolo-[3,2-d][1]benzazepin-6(5)-one

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A propos de cet article

Formule empirique (notation de Hill) :
C16H11N3O3
Numéro CAS:
237430-03-4
Poids moléculaire :
293.28
UNSPSC Code:
12352200
PubChem Substance ID:
24890918
NACRES:
NA.77
MDL number:
MFCD02683579

Principaux documents

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Nom du produit

Alsterpaullone, ≥98% (HPLC), powder

SMILES string

[O-][N+](=O)c1ccc2[nH]c-3c(CC(=O)Nc4ccccc-34)c2c1

InChI key

OLUKILHGKRVDCT-UHFFFAOYSA-N

InChI

1S/C16H11N3O3/c20-15-8-12-11-7-9(19(21)22)5-6-14(11)18-16(12)10-3-1-2-4-13(10)17-15/h1-7,18H,8H2,(H,17,20)

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

yellow to brown

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

Quality Level

100

Gene Information

rat ... Gsk3b(84027)

Catégories apparentées

Application

Alsterpaullone has been used to stabilize β-catenin.
Alsterpaullone inhibits GSK-3β, CDK5/p25, and CDK1/cyclin B. Alsterpaullone has also been studied as an antimanic therapeutic for the acute manic phase of bipolar disorder.

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.
Potent and selective inhibitor of GSK-3β and CDK5/p25; potent inhibitor of CDK1/cyclin B (IC50 = 0.035 μM).

Features and Benefits

This compound is featured on the CDKs and GSK-3 pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
0000368652
0000364269
0000368652
0000364269
0000173216

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Consulter la Bibliothèque de documents

Laura Iglesias Ollé et al.
Biomedicines, 12(6) (2024-06-27)
Hydra head formation depends on an organizing center in which Wnt/β-catenin signaling, that plays an inductive role, positively regulates Sp5 and Zic4, with Sp5 limiting Wnt3/β-catenin expression and Zic4 triggering tentacle formation. Using transgenic lines in which the HySp5 promoter
C Schultz et al.
Journal of medicinal chemistry, 42(15), 2909-2919 (1999-07-30)
The paullones represent a novel class of small molecule cyclin-dependent kinase (CDK) inhibitors. To investigate structure-activity relationships and to develop paullones with antitumor activity, derivatives of the lead structure kenpaullone (9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one, 4a) were synthesized. Paullones with different substituents in the
Mikhail Kalinichev et al.
The international journal of neuropsychopharmacology, 14(8), 1051-1067 (2011-01-07)
There is a growing body of evidence suggesting that animal models can be developed to probe the specific domains of bipolar disorder (BD) using the endophenotype approach. Here we tested clinically active antimanic drugs to validate amphetamine-induced hyperactivity in Black
Michael Trevino et al.
Developmental dynamics : an official publication of the American Association of Anatomists, 240(12), 2673-2679 (2011-11-05)
Although regeneration is widespread among metazoa, the molecular mechanisms have been studied in only a handful of taxa. Of these taxa, fewer still are amenable to studies of embryogenesis. Our understanding of the evolution of regeneration, and its relation to
Alsterpaullone, a cyclin-dependent kinase inhibitor, mediated toxicity in HeLa cells through apoptosis-inducing effect
Cui C, et al.
Journal of Analytical Methods in Chemistry, 2013(25) (2013)
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