SML1481

FzM1

≥98% (HPLC)

• Synonym(s): 1-(3-Hydroxy-5-(thiophen-2-yl)phenyl)-3-(naphthalen-2-yl)urea
• Empirical Formula (Hill Notation): C₂₁H₁₆N₂O₂S
• CAS Number: 1680196-54-6
• Molecular Weight: 360.43
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825910
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 20 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: O=C(NC1=CC(C=CC=C2)=C2C=C1)NC3=CC(C4=CC=CS4)=CC(O)=C3
• InChI: 1S/C21H16N2O2S/c24-19-12-16(20-6-3-9-26-20)11-18(13-19)23-21(25)22-17-8-7-14-4-1-2-5-15(14)10-17/h1-13,24H,(H2,22,23,25)
• InChI key: OBTSACXGWYGCPK-UHFFFAOYSA-N

Description

Biochem/physiol Actions

FzM1 is an allosteric ligand of the Frizzled4 (Fz4) receptor and a Wnt/β-catenin pathway inhibitor, found by a screen for pharmacological chaperones for a misfolded mutant of the Frizzled4 (Fz4) receptor. FzM1 is believed to induce conformational changes in Fz4 by interacting with the third intracellular loop, ICL3, inhibiting binding of dishevelled (Dsh) and hampering the formation of the Fz4-Dsh complex that is necessary for β-catenin nuclear transport and ultimately transcription of TCF/LEF-regulated genes. FzM1 was tested on two tumor cell lines. U87MG glioblastoma cells acquired a more differentiated phenotype on application. FzM1 and FzM1alk also sped up the differentiation of Caco-2 cells. FzM1 has a log EC50 value of 5.74 for inhibition of Wnt antagonism.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3