4-(di(1H-indol-3-yl)Methyl)phenol Chemical Properties

Melting point:

122-124 °C

Boiling point:

610.2±50.0 °C(Predicted)

Density 

1.321±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in DMSO (35 mg/ml); ethanol (35 mg/ml)

form 

solid

pka

9.98±0.26(Predicted)

color 

Pink

Stability:

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

4-(di(1H-indol-3-yl)Methyl)phenol Usage And Synthesis

Description

C-DIM 8 (151358-47-3) is an antagonist of the orphan nuclear receptor Nur77 (NR4A1, TR3).1 Induces reactive oxygen species and ER stress in pancreatic cancer cells.2 C-DIM 8 mimics the effect of Nur77 knockdown in non-small-cell lung cancer A549 and H460 cells, inhibiting cell growth and inducing apoptosis which was accompanied by decreased expression of survivin and inhibition of mTORC1 signaling.3 Inhibits the expression of β1- and β3-integrin and blocks integrin-dependent breast cancer cell migration.4 Decreases expression of the histone methyltransferase G9A (EHMT2) in a variety of cancer cell lines.5

Uses

DIM-C-pPhOH is a nuclear receptor 4A1 (NR4A1) antagonist. DIM-C-pPhOH inhibits cancer cell growth and mTOR signaling, induce apoptosis and cellular stress. DIM-C-pPhOH reduces cell proliferation with IC50 values of 13.6 μM and 13.0 μM for ACHN cells and 786-O cells, respectively[1].

Synthesis

GENERAL METHODS: BiVO4 nanoparticles (BiVO4-NPs, 30 mg) were added to a mixture containing indole or 2-methylindole (2 mmol) with aldehydes (1 mmol). The reaction mixture was stirred at 80 °C for an appropriate time under solvent-free conditions. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with 30 mL of hot ethanol and the catalyst was recovered by filtration and washed with ethanol (5 mL). The solvent was evaporated under reduced pressure and the remaining solid was recrystallized by a solvent mixture of ethanol/water (95:5, v/v) to give the pure product 4-(bis(1H-indol-3-yl)methyl)phenol. The spectral and physical data of all the products were in agreement with those reported in the literature and corresponded to samples prepared according to previously reported methods.

in vivo

IC 50

Nur77/NR4A1

storage

Store at -20°C

References

[1] SUDHAKAR CHINTHARLAPALLI. Activation of Nur77 by selected 1,1-Bis(3’-indolyl)-1-(p-substituted phenyl)methanes induces apoptosis through nuclear pathways.[J]. The Journal of Biological Chemistry, 2005, 280 26: 24903-24914. DOI:10.1074/jbc.m500107200
[2] SYNG-OOK LEE. The orphan nuclear receptor NR4A1 (Nur77) regulates oxidative and endoplasmic reticulum stress in pancreatic cancer cells.[J]. Molecular Cancer Research, 2014, 12 4: 527-538. DOI:10.1158/1541-7786.mcr-13-0567
[3] S-O LEE. The nuclear receptor TR3 regulates mTORC1 signaling in lung cancer cells expressing wild-type p53[J]. Oncogene, 2011, 31 27: 3265-3276. DOI:10.1038/onc.2011.504
[4] E. HEDRICK. NR4A1 Antagonists Inhibit β1-Integrin-Dependent Breast Cancer Cell Migration[J]. Molecular and Cellular Biology, 2016, 36 1: 1383-1394. DOI:10.1128/mcb.00912-15
[5] RUPESH SHRESTHA. The Histone Methyltransferase Gene G9A Is Regulated by Nuclear Receptor 4A1 in Alveolar Rhabdomyosarcoma Cells.[J]. Molecular Cancer Therapeutics, 2021, 20 3: 612-622. DOI:10.1158/1535-7163.mct-20-0474

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