Chemical Properties
Solid
Uses
3,3′-Diindolylmethane may be used as a model substrate to analyze the role of 3,3′-diindolylmethane in inducing apoptosis in human cancer cells.
Uses
An antineoplastic agent that activates Chk 2 and cytochrome p450
Definition
ChEBI: 3,3'-diindolylmethane is a member of indoles. It has a role as an antineoplastic agent and a P450 inhibitor.
General Description
3,3′-Diindolylmethane, a dimer of indole-3-carbinol, is a component of cruciferous vegetables. It is known to exhibit anticancer effects.
Biological Activity
3,3'-diindolylmethane is an anticancer agent [1].3,3'-diindolylmethane (dim) is a dimer of indole-3-carbinol generated in low ph environment. it inhibited cell growth with ic50 values of 17, 24 and 30 μm in mcf-7, t47d and saos2 cell lines, respectively. dim induced apoptosis in these cells without affecting the p53 pathway. in human nasopharyngeal carcinoma (npc) cell line (5-8f npc), treatment of dim decreased the ability of cell migration and invasion dose-dependently. in rats, transplanted with npc cells, dim administration resulted in suppressing lymph node metastasis. besides that, dim was found to induce erα target gene expression and the concomitant cell proliferation at low concentration (10μm) in the absence of e2 [1, 2 and 3].
Biochem/physiol Actions
Acid-catalyzed reaction product of a phytochemical naturally found in Brassicaceae, indole-3-carbinol. It functions as an antitumor agent. This derivative can both directly stimulate apoptosis at relatively high concentrations and sensitize TRAIL-induced apoptosis in human cancer cells. DIM induces a G1 cell cycle arrest in human breast cancer MCF-7 cells by a mechanism that includes increased expression of p21. DIM is a strong mitochondrial H+-ATPase inhibitor. The function of DIM and its derivatives as a new plant growth promoter has been studied in an eco-friendly system.
Synthesis
Indole (1.17 g,10 mmol), CTAB (50% mol) and oxalic acid (50% mol) were placed in a 25 ml single-necked round-bottomed flask, 5 ml of deionized water was added and stirred thoroughly for 5 min, then an aqueous solution of formaldehyde (0.38 g of solution, 5 mmol of formaldehyde) was added dropwise. The reaction was stopped for 3 hours at room temperature. The reaction solution was extracted with 15 ml of ethyl acetate in three portions and the organic phase was collected and dried with anhydrous Na2SO4 for 5 hours. The solvent was removed under reduced pressure and recrystallized from a mixed solution of methanol and water (methanol/H2O = 10/1) to give 3,3'-diindolylmethane as a white solid in 85% yield.
References
1. ge x, yannai s, rennert g, et al. 3, 3′-diindolylmethane induces apoptosis in human cancer cells. biochemical and biophysical research communications, 1996, 228(1): 153-158. 2. wu t, chen c, li f, et al. 3, 3' diindolylmethane inhibits the invasion and metastasis of nasopharyngeal carcinoma cells in vitro and in vivo by regulation of epithelial mesenchymal transition. experimental and therapeutic medicine, 2014, 7(6): 1635-1638. 3. marques m, laflamme l, benassou i, et al. low levels of 3, 3 [prime]-diindolylmethane activate estrogen receptor alpha and induce proliferation of breast cancer cells in the absence of estradiol. bmc cancer, 2014, 14(1): 524.
