3,3'-Diindolylmethane
Synonym(s):3,3′-Bisindolylmethane;DIM
- CAS NO.:1968-05-4
- Empirical Formula: C17H14N2
- Molecular Weight: 246.31
- MDL number: MFCD00195766
- EINECS: 100-201-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 19:05:58
What is 3,3'-Diindolylmethane ?
Chemical properties
Solid
The Uses of 3,3'-Diindolylmethane
apoptosis inducer
The Uses of 3,3'-Diindolylmethane
An antineoplastic agent that activates Chk 2 and cytochrome p450
The Uses of 3,3'-Diindolylmethane
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.
What are the applications of Application
3,3′-Diindolylmethane is 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.
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.
Properties of 3,3'-Diindolylmethane
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) |
form | Off-white powder. |
pka | 16.91±0.30(Predicted) |
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 |
CAS DataBase Reference | 1968-05-4(CAS DataBase Reference) |
Safety information for 3,3'-Diindolylmethane
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H413:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P273:Avoid release to the environment. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 3,3'-Diindolylmethane
InChIKey | VFTRKSBEFQDZKX-UHFFFAOYSA-N |
SMILES | C(C1C2=C(NC=1)C=CC=C2)C1C2=C(NC=1)C=CC=C2 |
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Neugen Labs
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Sami Sabinsa Group Limited (formerly Sami Labs Limited)
Earthchem Laboratories P Ltd
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