1129669-05-1

Basic information

• Product Name: IM-12
• Synonyms: IM-12;3-(4-fluorophenethylaMino)-1-Methyl-4-(2-Methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione;3-[[2-(4-fluorophenyl)ethyl]amino]-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione;3-(4-Fluorophenylethylamino)-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione IM-12;3-(4-Fluorophenylethylamino)-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione
• CAS NO: 1129669-05-1
• Molecular Formula: C₂₂H₂₀FN₃O₂
• Molecular Weight: 377.4115032
• Product Categories: Inhibitors
• Mol File: 1129669-05-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 187 °C
• Boiling Point: 600.2±55.0 °C(Predicted)
• Appearance: yellow-orange/
• Density: 1.34±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥9mg/mL
• PKA: 16.77±0.30(Predicted)
• CAS DataBase Reference: IM-12(CAS DataBase Reference)
• NIST Chemistry Reference: IM-12(1129669-05-1)
• EPA Substance Registry System: IM-12(1129669-05-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 1129669-05-1(Hazardous Substances Data)

Usage

Description

Glycogen synthase kinase 3β (GSK3β) is a constitutively active serine/threonine protein kinase implicated in several important regulatory processes. It can phosphorylate β-catenin, an intracellular signal transducer in the Wnt signaling pathway, which leads to β-catenin degradation. IM-12 is a non-symmetrically substituted indolylmaleimide that increases β-catenin levels by inhibiting GSK3β (IC50 = 53 nM). It has been shown to reduce proliferation and increase differentiation of a ReNCell VM cell line derived from human ventral midbrain. IM-12 is also reported to have a depolymerizing effect on in vitro tubulin assembly.

Uses

3-((4-Fluorophenethyl)amino)-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione acts as an enhancer of Wnt signalling, involved in cell proliferation or differentiation, via inhibition of glycogen synthase kinase 3 beta (GSK-3β).

references

[1]. schm?le ac, brennführer a, karapetyan g, et al. novel indolylmaleimide acts as gsk-3beta inhibitor in human neural progenitor cells. bioorg med chem, 2010, 18(18): 6785-6795.

Upstream product

• 885701-91-7 1-methyl-3-bromo-4-(2-methyl-1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione 
• 1583-88-6 4-fluoro-2-phenethylamine 
• 201230-82-2 carbon monoxide 

Relevant articles and documents

Novel indolylmaleimide acts as GSK-3β inhibitor in human neural progenitor cells

The Wnt pathway is involved in cellular processes linked to either proliferation or differentiation. Therefore small molecules offer an attractive opportunity to modulate this pathway, whereas the key enzyme GSK-3β is of special interest. In this study, non-symmetrically substituted indolylmaleimides have been synthesized and their ability to function as GSK-3β inhibitors has been investigated in a human neural progenitor cell line. Among the newly synthesized compounds, the substance IM-12 showed a significant activity in several biological tests which was comparable or even outplayed the effects of the known GSK-3β inhibitor SB-216763. Furthermore the treatment of human neural progenitor cells with IM-12 resulted in an increase of neuronal cells. Therefore we conclude that indolylmaleimides act via the canonical Wnt signalling pathway by inhibition of the key enzyme GSK-3β.