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DIM

Cat No.:V8964 Purity: ≥98%
3,3'-Diindolylmethane is a potent androgen receptor (AR) antagonist.
DIM
DIM Chemical Structure CAS No.: 1968-05-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
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Product Description
3,3'-Diindolylmethane is a potent androgen receptor (AR) antagonist.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Although 3,3'-Diindolylmethane (DIM) has less visible structural similarity to the endogenous AR ligand dihydrotestosterone (DHT), it is a powerful antagonist of androgen-acquisition receptor (AR) function. The primary byproduct of indole-3-carbinol digestion, which is a potentially anticancer ingredient in cruciferous products, is 3,3'-Diindolemethane. In L., 3,3'-Diindolylmethane demonstrates strong anticancer activity as well as antiandrogenic qualities. LNCaP cell proliferation is regulated by 3,3'-diindolylmethane, which also prevents DHT from stimulating DNA synthesis. Moreover, 3,3'-diindolylmethane suppresses DHT-induced stimulation in LNCaP cells and controls the equilibrium of endogenous PSA. Furthermore, the Pioneer promoter of the DHT victim controlled the expression of the reporter construct in suspension-transfected LNCaP cells by adjusting the 3,3′-diindolylmethane concentration. Co-administration of 50 μM 3,3'-diindolylmethane showed where AR was located in the cytoplasm and nucleus and partially prevented AR translocation brought on by DHT administration. Moreover, treatment with 3,3′-diindolylmethane inhibited the nucleus's ability to create AR foci. The sole source of fluorescein, which is mostly found in the cytoplasm, is 3,3'-diindolylmethane [1].
ln Vivo
For 30 days, subjects were split into two groups at random and given subcutaneous injections of either vehicle or 3,3'-diindolylmethane (10 mg/kg). Every three days, the subjects' body weight and tumor volume were measured with calipers. Treatment with 3,3'-Diindolylmethane (DIM) markedly slowed the growth of SNU-484 xenograft tumors. Interestingly, the turning body weight 30 days post-drug irradiation did not differ appreciably from the vehicle simulator's, suggesting that 3,3'-diindolylmethane is not highly harmful to mice. When combined, our results show that 3,3'-diindolylmethane strongly suppresses SNU-484 xenografts' ability to develop in vivo through YAP inactivation [2].
References

[1]. 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]. 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.

Additional Infomation
3,3'-diindolylmethane is a member of indoles. It has a role as an antineoplastic agent and a P450 inhibitor.
Diindolylmethane has been used in trials studying the prevention and treatment of SLE, Prostate Cancer, Cervical Dysplasia, Stage I Prostate Cancer, and Stage II Prostate Cancer, among others.
3,3'-Diindolylmethane has been reported in Brassica oleracea, Arundina graminifolia, and other organisms with data available.
Diindolylmethane is a phytonutrient and plant indole found in cruciferous vegetables including broccoli, Brussels sprouts, cabbage, cauliflower and kale, with potential anti-androgenic and antineoplastic activities. As a dimer of indole-3-carbinol, diindolylmethane (DIM) promotes beneficial estrogen metabolism in both sexes by reducing the levels of 16-hydroxy estrogen metabolites and increasing the formation of 2-hydroxy estrogen metabolites, resulting in increased antioxidant activity. Although this agent induces apoptosis in tumor cells in vitro, the exact mechanism by which DIM exhibits its antineoplastic activity in vivo is unknown.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H14N2
Molecular Weight
246.30646
Exact Mass
246.115
CAS #
1968-05-4
PubChem CID
3071
Appearance
Off-white to pink solid powder
Density
1.3±0.1 g/cm3
Boiling Point
504.8±30.0 °C at 760 mmHg
Melting Point
167 °C
Flash Point
232.5±15.8 °C
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.765
LogP
4.05
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
0
Rotatable Bond Count
2
Heavy Atom Count
19
Complexity
286
Defined Atom Stereocenter Count
0
SMILES
C1(CC2=CNC3=C2C=CC=C3)=CNC4=C1C=CC=C4
InChi Key
VFTRKSBEFQDZKX-UHFFFAOYSA-N
InChi Code
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
Chemical Name
3-(1H-indol-3-ylmethyl)-1H-indole
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~405.99 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (10.15 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (10.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.0599 mL 20.2996 mL 40.5992 mL
5 mM 0.8120 mL 4.0599 mL 8.1198 mL
10 mM 0.4060 mL 2.0300 mL 4.0599 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
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  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01846364 TERMINATED Dietary Supplement: Diindolylmethane (DIM) Proliferative Thyroid Disease The New York Eye & Ear Infirmary 2006-11 Early Phase 1
NCT00392652 COMPLETED Drug: oral microencapsulated diindolylmethane Healthy, no Evidence of Disease National Cancer Institute (NCI) 2006-11 Phase 1
NCT00212381 COMPLETED Drug: di indolylmethane (DIM)
Dietary Supplement: Red rice bran
Cervical Dysplasia New York Presbyterian Hospital 2000-09 Phase 3
NCT02525159 COMPLETED Dietary Supplement: DIM pills
Other: Placebo Pill
Breast Cancer Instituto Nacional de Perinatologia Isidro Espinosa de los Reyes 2006-08 Phase 3
NCT01022333 UNKNOWN STATUS Dietary Supplement: Diindolylmethane (DIM) Breast Cancer Women's College Hospital 2009-07 Phase 1
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