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A3734

Sigma-Aldrich

1-Azakenpaullone

≥97% (HPLC)

Synonym(s):

9-Bromo-7,12-dihydro-pyrido[3′,2′:2,3]azepino[4,5-b]indol-6(5H)-one

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About This Item

Empirical Formula (Hill Notation):
C15H10BrN3O
CAS Number:
676596-65-9
Molecular Weight:
328.16
MDL number:
MFCD09037522
UNSPSC Code:
12352200
PubChem Substance ID:
329770845
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

storage condition

protect from light

color

gray-brown

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

O=C1CC2=C(NC3=C2C=C(Br)C=C3)C4=C(C=CC=N4)N1

InChI

1S/C15H10BrN3O/c16-8-3-4-11-9(6-8)10-7-13(20)18-12-2-1-5-17-15(12)14(10)19-11/h1-6,19H,7H2,(H,18,20)

InChI key

NTSBZVCEIVPKBJ-UHFFFAOYSA-N

Biochem/physiol Actions

1-Azakenpaullone (AZP) can stimulate the transcription of β-catenin-related genes. This compound can induce the multiplication and replication of β cell.
1-Azakenpaullone is a cell permeable, potent, selective inhibitor of glycogen synthase kinase 3β (GSK3β) with 100-fold less cross-reactivity against CDKs. 1-Azakenpaullone can be used together with BIO and CHIR99021 as "gold standards" for GSK3 inhibition.

Caution

air sensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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9-cyano-1-azapaullone (cazpaullone), a glycogen synthase kinase-3 (GSK-3) inhibitor activating pancreatic beta cell protection and replication
Stukenbrock H, et al.
Journal of medicinal chemistry, 51(7), 2196-2207 (2008)
Thiranut Jaroonwitchawan et al.
Biochemical and biophysical research communications, 481(1-2), 176-181 (2016-11-07)
Neural crest (NC) is a transient population, arising during embryonic development and capable of differentiating into various somatic cells. The defects of neural crest development leads to neurocristopathy. Several signaling pathways were revealed their significance in NC cell specification. Fibroblast
Rong Hu et al.
Stem cells translational medicine, 6(1), 121-130 (2017-02-09)
Allogeneic hematopoietic stem cell transplantation (HSCT) is a potentially curative therapy for many malignant and nonmalignant diseases. However, chronic graft-versus-host disease (cGVHD) remains a significant cause of late morbidity and mortality after allogeneic HSCT. cGVHD often manifests as autoimmune syndrome.
Charles W Tran et al.
Journal of immunology (Baltimore, Md. : 1950), 199(12), 4056-4065 (2017-11-08)
The decision between T cell activation and tolerance is governed by the spatial and temporal integration of diverse molecular signals and events occurring downstream of TCR and costimulatory or coinhibitory receptor engagement. The PI3K-protein kinase B (PKB; also known as
Combination effects of AHR agonists and Wnt beta-catenin modulators in zebrafish embryos: implications for physiological and toxicological AHR functions
Wincent E, et al.
Toxicology and Applied Pharmacology, 284(2), 163-179 (2015)
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Glycogen Synthase Kinase 3 (GSK-3) Overview

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