A4847
Alsterpaullone
≥98% (HPLC), powder
Synonym(s):
9-Nitro-7,12-dihydroindolo-[3,2-d][1]benzazepin-6(5)-one
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About This Item
Empirical Formula (Hill Notation):
C16H11N3O3
CAS Number:
Molecular Weight:
293.28
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
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)
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 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
Certificates of Analysis (COA)
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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
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.
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
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
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