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SML0211 Sigma-Aldrich

iCRT3

Synonym: 2-[[[2-(4-ethylphenyl)-5-methyl-4-oxazolyl]methyl]thio]-N-(2-phenylethyl)acetamide

  • CAS Number 901751-47-1

  • Empirical Formula (Hill Notation) C23H26N2O2S

  • Molecular Weight 394.53

  •  MDL number MFCD14766288

  •  PubChem Substance ID 329825232

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, DNA-RNA Transcription Regulators,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
storage condition   desiccated
color   white to tan
solubility   DMSO: ≥5 mg/mL
storage temp.   2-8°C
SMILES string   CCc1ccc(cc1)-c2nc(CSCC(=O)NCCc3ccccc3)c(C)o2
InChI   1S/C23H26N2O2S/c1-3-18-9-11-20(12-10-18)23-25-21(17(2)27-23)15-28-16-22(26)24-14-13-19-7-5-4-6-8-19/h4-12H,3,13-16H2,1-2H3,(H,24,26)
InChI key   QTDYVSIBWGVBKU-UHFFFAOYSA-N

Description

General description

iCRT3 is a small cell-permeable oxazole compound. It blocks cytokine secretion in lipopolysaccharide (LPS)-stimulated macrophages.

Application

iCRT3 has been used to inhibit the interactions between β-catenin and transcription factor (TCF).

iCRT3 has been used:
• for β- catenin inhibition in dual luciferase assay
• to inhibit β-catenin /TCF interactions and their transcriptional activity
• as wingless/tailess (wnt) antagonist, to determine Wnt/β-catenin signaling is essential for PROX1-mediated regulation of forkhead box protein C2 (FOXC2)(3)catenin inhibition in dual luciferase assay
• to inhibit β- catenin /TCF interactions and their transcriptional activity
• as wingless/tailess (wnt) antagonist, to determine Wnt/β-catenin signaling is essential for PROX1-mediated regulation of forkhead box protein C2 (FOXC2)

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

The key mediator of Wnt signaling is the transcriptional co-activator b-catenin. In the cytoplasm, b-catenin is tightly bound to a complex that includes Axin and GSK-3b. Stimulation causes b-catenin stabilization, translocation to the nucleus and association with TCF4 to initiate transcription of responsive genes, referred to as Catenin Responsive Transcription (CRT). Virtually all Wnt-associated cancers are the result of misregulated CRT. Three inhibitors of CRT (iCRT) were identified in a screen that employed RNAi based knockdown of Axin, which stimulates CRT without affecting upstream mechanisms such as GSK activity, transduction by disheveled / frizzled, etc. These compounds are potent inhibitors of CRT reporter genes, as well as endogenous gene targets. The compounds also disrupt b-catenin-TCF4 interaction in a dose dependent manner, and cause G0/G1 arrest in colon tumor lines.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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