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SML0339

Sigma-Aldrich

Tideglusib

≥98% (HPLC)

Synonym(s):

4-Benzyl-2-(naphthalen-1-yl)-[1,2,4]thiadiazolidine-3,5-dione, NP-12, NP031112

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About This Item

Empirical Formula (Hill Notation):
C19H14N2O2S
CAS Number:
865854-05-3
Molecular Weight:
334.39
MDL number:
MFCD18633296
UNSPSC Code:
12352200
PubChem Substance ID:
329825344
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: >15 mg/mL

storage temp.

2-8°C

SMILES string

O=C1SN(C(=O)N1Cc2ccccc2)c3cccc4ccccc34

InChI

1S/C19H14N2O2S/c22-18-20(13-14-7-2-1-3-8-14)19(23)24-21(18)17-12-6-10-15-9-4-5-11-16(15)17/h1-12H,13H2

InChI key

PMJIHLSCWIDGMD-UHFFFAOYSA-N

Gene Information

human ... GSK3B(2932)

Application

Tideglusib has been used:
  • as a reference compound in ADP-GloTM Kinase assay
  • as an allosteric inhibitor of GSK-3β to study its effects on myocardial remodeling and angiogenesis
  • as a differentiation agent (specifically a glycogen synthase kinase (GSK)-3β inhibitor) to convert fibroblast cells into octamer-binding transcription factor-4 (OCT4)+ and vascular endothelial growth factor receptor-2 (VEGFR-2/fetal liver kinase-1 (FLK1)+ cells

Biochem/physiol Actions

Tideglusib, also known as NP031112 or NP-12, is a potent non ATP-competitive inhibitor of glycogen synthase kinase-3 (GSK3), an important kinase studied in stem cell research and neurodegenerative diseases. It is currently in clinical trials for Alzheimer′s disease and Progressive Supranuclear Palsy (PSP). Tideglusib reduces phosphorylation of the tau protein and the accumulation of amyloid plaques, reduces hippocampal and entorhinal cortex neuron loss and improves spatial memory deficits. It has also shown neuroprotective and anti-inflammatory activity in a variety of animal models.

Features and Benefits

This compound is featured on the GSK-3 page 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

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Certificates of Analysis (COA)

Lot/Batch Number
0000236893
0000212778
0000236893
0000212778
0000176984

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Chromatin-modifying agents convert fibroblasts to OCT4+ and VEGFR-2+ capillary tube-forming cells
Wary A, et al.
Testing, 12(5), e0176496-e0176496 (2017)
Pottayil G Sasikumar et al.
Molecular cancer therapeutics, 18(6), 1081-1091 (2019-04-25)
Pioneering success of antibodies targeting immune checkpoints such as PD-1 and CTLA4 has opened novel avenues for cancer immunotherapy. Along with impressive clinical activity, severe immune-related adverse events (irAE) due to the breaking of immune self-tolerance are becoming increasingly evident
The allosteric glycogen synthase kinase-3 inhibitor NP12 limits myocardial remodeling and promotes angiogenesis in an acute myocardial infarction model
Baruah J, et al.
The Journal of Biological Chemistry, 292(50), 20785-20798 (2017)
Combined Shape-Based Screening and Molecular Docking Approach
Chauhan N, et al.
International Journal of Pharmaceutical Sciences and Drug Research, 9(3), 145-148 (2017)

Articles

Glycogen Synthase Kinase 3 (GSK-3) Overview

Glycogen synthase kinase 3 (GSK-3) is a highly conserved family of serine/threonine kinases for over 100 proteins in many pathways. See a list of accepted GSK-3 modulators and related products.

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