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Key Documents

A4847

Sigma-Aldrich

Alsterpaullone

≥98% (HPLC), powder

Synonyma:

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

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen


About This Item

Empirický vzorec (Hillův zápis):
C16H11N3O3
Číslo CAS:
Molekulová hmotnost:
293.28
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

yellow to brown

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

SMILES string

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

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)

InChI key

OLUKILHGKRVDCT-UHFFFAOYSA-N

Gene Information

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Navštívit knihovnu dokumentů

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
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
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
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
Identification of alsterpaullone as a novel small molecule inhibitor to target group 3 medulloblastoma
Faria C C, et al.
Testing, 6(25), 21718-21718 (2015)

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