3,3'-Diindolylmethane

Modify Date: 2024-01-02 15:25:45

3,3'-Diindolylmethane Structure
3,3'-Diindolylmethane structure
 Common Name 3,3'-Diindolylmethane
CAS Number 1968-05-4 Molecular Weight 246.307
Density 1.3±0.1 g/cm3 Boiling Point 504.8±30.0 °C at 760 mmHg
Molecular Formula C17H14N2 Melting Point 167 °C
MSDS USA Flash Point 232.5±15.8 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of 3,3'-Diindolylmethane


3,3'-Diindolylmethane is a strong, pure androgen receptor (AR) antagonist.

 Names

Name 3,3'-diindolylmethane
Synonym More Synonyms

 3,3'-Diindolylmethane Biological Activity

Description 3,3'-Diindolylmethane is a strong, pure androgen receptor (AR) antagonist.
Related Catalog
Target

Androgen receptor[1]

In Vitro 3,3'-Diindolylmethane (DIM) is a strong antagonist of androgen receptor (AR) function but exhibits less than obvious structural similarity to the endogenous AR ligand, dihydrotestosterone (DHT). 3,3'-Diindolylmethane is a major digestive product of indole-3-carbinol, a potential anticancer component of cruciferous vegetables. 3,3'-Diindolylmethane exhibits potent antiproliferative and antiandrogenic properties in androgen-dependent human prostate cancer cells. 3,3'-Diindolylmethane suppresses cell proliferation of LNCaP cells and inhibits DHT stimulation of DNA synthesis. Moreover, 3,3'-Diindolylmethane inhibits endogenous PSA transcription and reduced intracellular and secreted PSA protein levels induced by DHT in LNCaP cells. Also, 3,3'-Diindolylmethane inhibits, in a concentration-dependent manner, the DHT-induced expression of a prostate-specific antigen promoter-regulated reporter gene construct in transiently transfected LNCaP cells. Co-treatment with 50 μM 3,3'-Diindolylmethane partially inhibits the translocation of AR induced by DHT treatment and showed distribution of the AR to be both cytoplasmic and nuclear. Furthermore, 3,3'-Diindolylmethane treatment prevents the formation of AR foci in the nucleus. 3,3'-Diindolylmethane alone produces a predominantly cytoplasmic distribution of fluorescence[1].
In Vivo Mice are randomized into two groups and are treated daily s.c. with either vehicle or 3,3'-Diindolylmethane (10 mg/kg) for 30 days. Tumor volume and the weight of mice are recorded once every 3 days using calipers. 3,3'-Diindolylmethane (DIM) treatment resulted in a marked inhibition of SNU-484 xenograft tumor growth. Notably, the body weight of mice from both groups did not significantly differ from the vehicle control following 30 days of drug exposure, suggesting that 3,3'-Diindolylmethane has no severe toxicity to the mice. Taken together, these findings demonstrate that 3,3'-Diindolylmethane administration significantly inhibited SNU-484 xenograft growthin vivo mediated by the inactivation of YAP[2].
Cell Assay The human prostate adenocarcinoma cell lines LNCaP-FGC and PC-3 are grown as adherent monolayers in 10% FBS-DMEM, supplemented with 4.0 g/L glucose and 3.7 g/L sodium bicarbonate in a humidified incubator at 37°C and 5% CO2, and passaged at ~80% confluency. Cultures used in subsequent experiments are at less than 40 passages. Cells grown in stripped conditions are in 5% DCC-FBS-DMEM base supplemented with 4 g/L glucose, 3.7 g/L sodium bicarbonate, and 0.293 g/L L-glutamine. Before the beginning of the treatments, cells are depleted of androgen for 4-7 days in medium composed of DMEM base without phenol red and with 4 g/L glucose and 3.7 g/L sodium bicarbonate. During the depletion period, medium is changed every 48 h. Treatments are administered by the addition of 1 μL of a 1,000-fold concentrated solution of 3,3'-Diindolylmethane in Me2SO/mL of medium. Once the treatment period started, medium is changed daily to counter possible loss of readily metabolized compounds[1].
Animal Admin Mice[2] Four-week-old female SPF/VAF immunodeficient mice are injected subcutaneously (s.c.) into the right flank with 0.1 mL Matrigel containing 3.5×106 human gastric cancer cells (SNU-484). The mice are randomized into 2 groups 1 week after tumor implantation: i) the untreated control group (n=5, DMSO in 50 μL PBS daily) and ii) the 3,3'-Diindolylmethane-treated group (n=5, 10 mg/kg in 50 μL PBS once daily). Gastric primary tumors are excised, and the final tumor volume is measured once every 3 days using a caliper and calculated as (width)2×length/2. The experiment is terminated on day 39. Half of the tumor tissue is prepared for western blotting and the other half is snap frozen in liquid nitrogen and stored at −80°C.
References

[1]. Le HT, et al. Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells. J Biol Chem. 2003 Jun 6;278(23):21136-45.

[2]. Li XJ, et al. 3,3'-Diindolylmethane suppresses the growth of gastric cancer cells via activation of the Hippo signaling pathway. Oncol Rep. 2013 Nov;30(5):2419-26.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 504.8±30.0 °C at 760 mmHg
Melting Point 167 °C
Molecular Formula C17H14N2
Molecular Weight 246.307
Flash Point 232.5±15.8 °C
Exact Mass 246.115692
PSA 31.58000
LogP 4.05
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.765
Storage condition 2-8°C

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335-H413
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases 22-24/25
RIDADR NONH for all modes of transport
RTECS NM0332000
HS Code 2933990090

 Synthetic Route

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

HB 236
1H-Indole, 2-(1H-indol-3-ylmethyl)-
3-(1H-indol-3-ylmethyl)-1H-indole
ARUNDINE
di(1H-indol-3-yl)methane
DI-3-INDOLYLMETHANE
DIM
3-DIINDOLYL METHANE
3,3'-Diindolylmethane
1H-Indole, 3,3'-methylenebis-
2-(1H-Indol-3-ylmethyl)-1H-indole
3,3'-Methylenediindole
3,3'-Methylenebisindole；DIM
DI INDOLYL METHANE
di-(1H-3-indolyl)methane
Indole dimer
3,3'-methylene-bis(1H-indole)
3,3-Methylenediindole
Indolyl-CH2-Indolyl
MFCD00195766
3,3'-Methylenebis(1H-indole)
3,3'-Diindolymetane
Diindole methane
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