SB216763 Chemical Properties

Melting point:

287-288.6 °C(lit.)

Boiling point:

598.1±50.0 °C(Predicted)

Density 

1.47±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: 20 mg/mL, soluble

form 

Orange solid

pka

7.27±0.60(Predicted)

color 

orange

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

InChI

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)

InChIKey

JCSGFHVFHSKIJH-UHFFFAOYSA-N

SMILES

N1C(=O)C(C2C3=C(N(C)C=2)C=CC=C3)=C(C2=CC=C(Cl)C=C2Cl)C1=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

SB216763 Usage And Synthesis

Description

SB-216763 (280744-09-4) is a potent and selective inhibitor of glycogen synthase kinase-1 (GSK-3) IC50=34.3 nM.1 Acts at the ATP-binding domain. Displays protective effects in lung fibrosis mouse model.2 Displays neuroprotective effects on cultured neurons.3 SB-216763 maintains mouse embryonic stem cells in a pluripotent state.4?Cell permeable.

Uses

SB 216763 is a potent and selective cell permeale ATP-competitive inhibitor of GSK3a. It stimulates glycogen synthesis in Chang human liver cells.

Uses

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

Definition

ChEBI: 3-(2,4-dichlorophenyl)-4-(1-methyl-3-indolyl)pyrrole-2,5-dione is a member of indoles and a member of maleimides.

Biological Activity

Potent and selective glycogen synthase kinase-3 (GSK-3) inhibitor (K i = 9 nM for GSK-3 α ); competes with ATP. Has minimal activity against 24 other protein kinases (IC 50 > 10 μ M). Stimulates glycogen synthesis, gene transcription and is neuroprotective.

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.

storage

Room temperature

References

[1] M P COGHLAN. Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription.[J]. Chemistry & biology, 2000, 7 10: 793-803. DOI:10.1016/s1074-5521(00)00025-9
[2] CARMELA GURRIERI. 3-(2,4-dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (SB216763), a glycogen synthase kinase-3 inhibitor, displays therapeutic properties in a mouse model of pulmonary inflammation and fibrosis.[J]. Journal of Pharmacology and Experimental Therapeutics, 2010, 332 3: 785-794. DOI:10.1124/jpet.109.153049
[3] D. CROSS. Selective small-molecule inhibitors of glycogen synthase kinase-3 activity protect primary neurones from death.[J]. Journal of Neurochemistry, 2001, 77 1: 94-102. DOI:10.1046/j.1471-4159.2001.t01-1-00251.x
[4] LESLIE A KIRBY. Glycogen synthase kinase 3 (GSK3) inhibitor, SB-216763, promotes pluripotency in mouse embryonic stem cells.[J]. PLoS ONE, 2012: e39329. DOI:10.1371/journal.pone.0039329

SB216763(280744-09-4)Related Product Information

• WIN 55,212-2 MESYLATE
• SB 225002
• SB 743921
• Ispinesib
• 4-BENZYL-2-METHYL-1,2,4-THIADIAZOLIDINE-3,5-DIONE
• SB 415286
• 1-AZAKENPAULLONE
• KAHWEOL
• SEDANOLIDE
• S-[N-(3-PHENYLPROPYL)(THIOCARBAMOYL)]-L-CYSTEINE
• CAFESTOL
• 2-THIO(3-IODOBENZYL)-5-(1-PYRIDYL)-[1,3,4]-OXADIAZOLE
• MK-2206 2HCl
• Saracatinib
• LDE225 (NVP-LDE225,Erismodegib)
• 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-
• Ibrutinib
• 2-(5-Benzo[1,3]dioxol-5-yl-2-tert-butyl-3H-imidazol-4-yl)-6-methylpyridine hydrate hydrochloride