3,3'-Diindolylmethane Property

Melting point:

167 °C

Boiling point:

230 °C(Press: 0.01 Torr)

Density 

1.271±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

16.91±0.30(Predicted)

form 

Off-white powder.

color 

White to Pale Beige

InChI

InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2

InChIKey

VFTRKSBEFQDZKX-UHFFFAOYSA-N

SMILES

C(C1C2=C(NC=1)C=CC=C2)C1C2=C(NC=1)C=CC=C2

LogP

4.401 (est)

CAS DataBase Reference

1968-05-4(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-26

WGK Germany 

3

RTECS 

NM0332000

HazardClass 

IRRITANT

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3,3'-Diindolylmethane Chemical Properties,Usage,Production

Chemical Properties

Solid

Uses

apoptosis inducer

Uses

An antineoplastic agent that activates Chk 2 and cytochrome p450

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.

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.

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.