3,3'-Diindolylmethane (Synonyms: DIM; Arundine; HB 236)

Name: 3,3'-Diindolylmethane
Brand: MedChemExpress
SKU: HY-15758
Rating: 5.0 (12 reviews)

Cat. No.: HY-15758 Purity: 99.93%: FAQs
Data Sheet SDS COA Handling Instructions

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

For research use only. We do not sell to patients.

3,3'-Diindolylmethane Chemical Structure

CAS No. : 1968-05-4

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10 mM * 1 mL in DMSO ready for reconstitution	USD 73	In-stock	Estimated Time of Arrival: December 31
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Based on 12 publication(s) in Google Scholar

Other Forms of 3,3'-Diindolylmethane:

3,3'-Diindolylmethane (Standard) Get quote

10 Publications Citing Use of MCE 3,3'-Diindolylmethane

IHC

: 3,3'-Diindolylmethane purchased from MedChemExpress. Usage Cited in: J Exp Clin Cancer Res. 2020 Jun 16;39(1):113. [Abstract]; IHC results of xenografts staining shows downexpression of AHR, RhoA, ROCK1, COX2 and mesenchymal cell markers as well as upregulation of epithelial cell marker Claudin-1.

: 3,3'-Diindolylmethane purchased from MedChemExpress. Usage Cited in: J Cell Commun Signal. 2020 Jun;14(2):175-192. [Abstract]; Western blot shows the results that at the 48 h time point, cells exerted the potent reactivity when exposing DIM treatment in that the expression of AHR reduces gradually on the basis of increased DIM concentrations and the production of CYP1A1 increases in the same way.

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Protocol
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Description

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

IC₅₀ & Target

Androgen receptor^[1]

Cellular Effect

Cell Line	Type	Value	Description	References
CHO	EC₅₀	0.368 μM Compound: 8; DIM	Positive allosteric modulation of recombinant human GPR84 expressed in CHO cell membranes co-expressing beta-arrestin2 assessed as increase in [3H]PSB-1584 binding measured after 6 hrs by scintillation counting method Positive allosteric modulation of recombinant human GPR84 expressed in CHO cell membranes co-expressing beta-arrestin2 assessed as increase in [3H]PSB-1584 binding measured after 6 hrs by scintillation counting method	[PMID: 31721581]
CHO	EC₅₀	0.5 μM Compound: 8; DIM	Agonist activity at human N-terminal FLAG-tagged GPR84 receptor stably expressed in CHO cell membranes assessed as stimulation of [35S]GTPgammaS binding incubated for 1 hr by liquid scintillation counting method Agonist activity at human N-terminal FLAG-tagged GPR84 receptor stably expressed in CHO cell membranes assessed as stimulation of [35S]GTPgammaS binding incubated for 1 hr by liquid scintillation counting method	[PMID: 31721581]
CHO	EC₅₀	0.7 μM Compound: 8; DIM	Agonist activity at human N-terminal FLAG-tagged GPR84 receptor stably expressed in CHO cells assessed as inhibition of forskolin-induced cAMP production preincubated for 20 mins followed by forskolin addition and measured after 20 mins Agonist activity at human N-terminal FLAG-tagged GPR84 receptor stably expressed in CHO cells assessed as inhibition of forskolin-induced cAMP production preincubated for 20 mins followed by forskolin addition and measured after 20 mins	[PMID: 31721581]
HEK293	EC₅₀	1.11 μM Compound: 8; DIM	Agonist activity at recombinant human HA-tagged GPR84 stably expressed in HEK293 cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by liquid scintillation counting method Agonist activity at recombinant human HA-tagged GPR84 stably expressed in HEK293 cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by liquid scintillation counting method	[PMID: 31721581]
MCF7	IC₅₀	50 μM Compound: DIM	Growth inhibition of human MCF7 cells after 48 hrs by MTT assay Growth inhibition of human MCF7 cells after 48 hrs by MTT assay	[PMID: 22277074]
MDA-MB-231	IC₅₀	10 μM Compound: DIM	Growth inhibition of human MDA-MB-231 cells after 48 hrs by MTT assay Growth inhibition of human MDA-MB-231 cells after 48 hrs by MTT assay	[PMID: 22277074]
Sf9	EC₅₀	11 μM Compound: 8; DIM	Agonist activity at human Gi1alpha-coupled GPR84 expressed in baculovirus infected Sf9 insect cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by top-count liquid scintillation counting method Agonist activity at human Gi1alpha-coupled GPR84 expressed in baculovirus infected Sf9 insect cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by top-count liquid scintillation counting method	[PMID: 31721581]
Sf9	EC₅₀	5.9 μM Compound: 8; DIM	Agonist activity at human Gi1alpha-coupled GPR84 expressed in baculovirus infected Sf9 insect cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by liquid scintillation counting method Agonist activity at human Gi1alpha-coupled GPR84 expressed in baculovirus infected Sf9 insect cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by liquid scintillation counting method	[PMID: 31721581]
U-251	EC₅₀	280 μM Compound: 6; DIM	Cytotoxicity against human U251 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay Cytotoxicity against human U251 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	[PMID: 28256372]

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

Molecular Weight

246.31

Formula

C₁₇H₁₄N₂

CAS No.

1968-05-4

Appearance

Solid

Color

Off-white to pink

SMILES

C1(CC2=CNC3=C2C=CC=C3)=CNC4=C1C=CC=C4

Structure Classification

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light, stored under nitrogen

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

Solvent & Solubility

In Vitro:

DMSO : ≥ 100 mg/mL (405.99 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	4.0599 mL	20.2994 mL	40.5988 mL
5 mM	0.8120 mL	4.0599 mL	8.1198 mL
10 mM	0.4060 mL	2.0299 mL	4.0599 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (10.15 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: 2.5 mg/mL (10.15 mM); Suspended solution; Need ultrasonic

This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 2.5 mg/mL (10.15 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

DMSO +

Tween-80 +

Saline

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Calculation results:

Working solution concentration: mg/mL

Method for preparing stock solution: mg drug dissolved in μL DMSO (Stock solution concentration: mg/mL).

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).

Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.

If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.

Purity & Documentation

Purity: 99.93%

Select Batch:

Data Sheet (283 KB) SDS (393 KB)

COA (253 KB) HNMR (123 KB) RP-HPLC (97 KB) GC (180 KB)

Handling Instructions (2659 KB)

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. [Content Brief]

[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. [Content Brief]

Cell Assay ^[1]	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]. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Animal Administration ^[2]	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. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
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. [Content Brief] [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. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	4.0599 mL	20.2994 mL	40.5987 mL	101.4969 mL
	5 mM	0.8120 mL	4.0599 mL	8.1197 mL	20.2994 mL
	10 mM	0.4060 mL	2.0299 mL	4.0599 mL	10.1497 mL
	15 mM	0.2707 mL	1.3533 mL	2.7066 mL	6.7665 mL
	20 mM	0.2030 mL	1.0150 mL	2.0299 mL	5.0748 mL
	25 mM	0.1624 mL	0.8120 mL	1.6239 mL	4.0599 mL
	30 mM	0.1353 mL	0.6766 mL	1.3533 mL	3.3832 mL
	40 mM	0.1015 mL	0.5075 mL	1.0150 mL	2.5374 mL
	50 mM	0.0812 mL	0.4060 mL	0.8120 mL	2.0299 mL
	60 mM	0.0677 mL	0.3383 mL	0.6766 mL	1.6916 mL
	80 mM	0.0507 mL	0.2537 mL	0.5075 mL	1.2687 mL
	100 mM	0.0406 mL	0.2030 mL	0.4060 mL	1.0150 mL

3,3'-Diindolylmethane Related Classifications

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Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

3,3'-Diindolylmethane1968-05-4DIM Arundine HB 236HB236HB 236HB-236Androgen ReceptorAutophagyInhibitorinhibitorinhibit

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3,3'-Diindolylmethane (Synonyms: DIM; Arundine; HB 236)

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Other Forms of 3,3'-Diindolylmethane:

3,3'-Diindolylmethane Related Antibodies

10 Publications Citing Use of MCE 3,3'-Diindolylmethane

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Complete Stock Solution Preparation Table

3,3'-Diindolylmethane Related Classifications

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