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Merck

A4847

Alsterpaullone

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

Synonym(e):

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

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1 MG

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Über diesen Artikel

Empirische Formel (Hill-System):
C16H11N3O3
CAS-Nummer:
Molekulargewicht:
293.28
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:

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Produktname

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

Gene Information

rat ... Gsk3b(84027)

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Dieser Artikel
126870SML0818W4016
assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

solid

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: ≥10 mg/mL

solubility

DMSO: 20 mg/mL

solubility

DMSO: 15 mg/mL, clear

solubility

DMSO: 10 mg/mL, clear

storage condition

desiccated

storage condition

OK to freeze, protect from light

storage condition

-

storage condition

-

Application

Alsterpaullone has been used to stabilize β-catenin.[1]
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.[2] 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.[3]
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.

Lagerklasse

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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Die Dokumentenbibliothek aufrufen

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
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
Tsuneo Takadera et al.
Neurotoxicity research, 21(3), 309-316 (2011-10-19)
In the central nervous system, members of the Src family of tyrosine kinases (SFKs) are widely expressed and are abundant in neurons. The purpose of this study is to examine whether glycogen synthase-3 (GSK-3) is involved in SFK inhibitor-induced apoptosis.
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
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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