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S3442

Sigma-Aldrich

SB 216763

>98% (HPLC)

Synonym(s):

3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

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About This Item

Empirical Formula (Hill Notation):
C19H12N2O2Cl2
CAS Number:
280744-09-4
Molecular Weight:
371.22
MDL number:
MFCD09753369
UNSPSC Code:
12352200
PubChem Substance ID:
24278616
NACRES:
NA.77

Quality Level

100

Assay

>98% (HPLC)

color

orange

solubility

DMSO: soluble 20 mg/mL
H2O: insoluble

originator

GlaxoSmithKline

storage temp.

−20°C

SMILES string

Cn1cc(C2=C(C(=O)NC2=O)c3ccc(Cl)cc3Cl)c4ccccc14

InChI

1S/C19H12Cl2N2O2/c1-23-9-13(11-4-2-3-5-15(11)23)17-16(18(24)22-19(17)25)12-7-6-10(20)8-14(12)21/h2-9H,1H3,(H,22,24,25)

InChI key

JCSGFHVFHSKIJH-UHFFFAOYSA-N

Gene Information

human ... GSK3A(2931) , GSK3B(2932)

Application

SB-216763 was used to inhibit GSK-3β in human brain microvascular endothelial cell line and colorectal cancer cells.

Biochem/physiol Actions

SB-216763 is a small molecule that competes with ATP and potently inhibits the activity α and β isozymes of GSK-3. It acts as neuroprotectant and prevents neuronal cell death induced by PI3-kinase pathway. It also delays preconditioning, reduces infarct size and prevents cardiac ischemia.
Potent, selective, cell permeable glycogen synthase kinase-3 (GSK-3) inhibitor.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GSK-3 and PKB/Akt pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Sold for research purposes under agreement from Glaxo­Smith­Kline

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)

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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Jonathan S Miller et al.
PloS one, 9(2), e88026-e88026 (2014-02-08)
The Akt - GSK3 signaling pathway has been recently implicated in psychostimulant-induced behavioral and cellular effects. Here, the ability of cocaine to regulate the activity of Akt and GSK3 was investigated by measuring the phosphorylation states of the two kinases.
Eric R Gross et al.
American journal of physiology. Heart and circulatory physiology, 294(3), H1497-H1500 (2008-01-29)
Previous studies in our laboratory suggest that an acute inhibition of glycogen synthase kinase 3 (GSK3) by SB-216763 (SB21) is cardioprotective when administered just before reperfusion. However, it is unknown whether the GSK inhibitor SB21 administered 24 h before ischemia
Giulia Rossana Gulino et al.
Environmental health perspectives, 124(6), 776-784 (2015-12-20)
Chrysotile asbestos accounts for > 90% of the asbestos used worldwide, and exposure is associated with asbestosis (asbestos-related fibrosis) and other malignancies; however, the molecular mechanisms involved are not fully understood. A common pathogenic mechanism for these malignancies is represented
Shuzhen Guo et al.
Stroke, 40(2), 652-655 (2008-11-01)
We recently reported that delayed lithium therapy can improve stroke recovery in rats by augmenting neurovascular remodeling. We tested the hypothesis that lithium can promote the expression of growth factors in brain endothelial cells and astrocytes. Human brain microvascular endothelial
Huan Deng et al.
The Journal of biological chemistry, 283(15), 10198-10207 (2008-02-07)
We examined the role of glycogen synthase kinase-3beta (GSK-3beta) inhibition in airway smooth muscle hypertrophy, a structural change found in patients with severe asthma. LiCl, SB216763, and specific small interfering RNA (siRNA) against GSK-3beta, each of which inhibit GSK-3beta activity
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