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

IM-12 is a non-symmetrically substituted indolylmaleimide that functions as an enhancer of Wnt signaling, which plays a crucial role in cell proliferation and differentiation. It achieves this by inhibiting glycogen synthase kinase 3 beta (GSK-3β), a constitutively active serine/threonine protein kinase involved in various regulatory processes. IM-12 increases β-catenin levels, which is an intracellular signal transducer in the Wnt signaling pathway, leading to a reduction in cell proliferation and an increase in differentiation. Additionally, IM-12 has been reported to have a depolymerizing effect on in vitro tubulin assembly.

Uses

Used in Pharmaceutical Industry:
IM-12 is used as a therapeutic agent for enhancing Wnt signaling, which is essential for cell proliferation and differentiation. Its ability to inhibit GSK-3β and increase β-catenin levels makes it a promising candidate for the treatment of various diseases and conditions that involve dysregulation of the Wnt signaling pathway.
Used in Neurodegenerative Disease Research:
IM-12 is used as a research tool for studying the effects of Wnt signaling modulation on neurodegenerative diseases. Its ability to reduce proliferation and increase differentiation of a ReNCell VM cell line derived from human ventral midbrain makes it a valuable compound for investigating the potential therapeutic effects of Wnt signaling modulation in neurodegenerative conditions.
Used in Cancer Research:
IM-12 is used as a research tool for studying the role of Wnt signaling in cancer cell proliferation and differentiation. Its inhibitory effect on GSK-3β and subsequent increase in β-catenin levels can provide insights into the development of novel cancer therapies targeting the Wnt signaling pathway.
Used in Drug Development:
IM-12 is used as a lead compound in the development of new drugs targeting the Wnt signaling pathway. Its potent inhibitory effect on GSK-3β (IC50 = 53 nM) and its ability to modulate Wnt signaling make it a promising starting point for the design and synthesis of new therapeutic agents for various diseases and conditions.

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.