A4847

Alsterpaullone

Name: Alsterpaullone
Brand: SIGMA
Price: 741 MYR

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

Synonym(s):

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

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1 MG

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₁₁N₃O₃

CAS Number:

237430-03-4

Molecular Weight:

293.28

MDL number:

MFCD02683579

UNSPSC Code:

12352200

PubChem Substance ID:

24890918

NACRES:

NA.77

Key Documents

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Product Name

Alsterpaullone, ≥98% (HPLC), powder

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

rat ... Gsk3b(84027)

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Show Differences

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This Item	SML0818	W4016	S7826
Sigma-Aldrich A4847 Alsterpaullone	Sigma-Aldrich SML0818 A-841720	Sigma-Aldrich W4016 Wedelolactone	Sigma-Aldrich S7826 SMER3
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form powder	form powder	form powder	form powder
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: ≥10 mg/mL	solubility DMSO: 15 mg/mL, clear	solubility DMSO: 10 mg/mL, clear	solubility DMSO: ≥30 mg/mL
storage condition desiccated	storage condition -	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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Paullones, a series of cyclin-dependent kinase inhibitors: synthesis, evaluation of CDK1/cyclin B inhibition, and in vitro antitumor activity.

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

Induction of canonical Wnt signaling by alsterpaullone is sufficient for oral tissue fate during regeneration and embryogenesis in Nematostella vectensis.

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

Evidence for antimanic efficacy of glycogen synthase kinase-3 (GSK3) inhibitors in a strain-specific model of acute mania.

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

Apoptosis induced by SRC-family tyrosine kinase inhibitors in cultured rat cortical cells.

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.

The genetic program for cartilage development has deep homology within Bilateria

Tarazona OA, et al.

Nature, 533(7601), 86-86 (2016)

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