D9568
3,3′-Diindolylmethane
≥98% (HPLC)
Synonym(s):
3,3′-Bisindolylmethane, DIM
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About This Item
Empirical Formula (Hill Notation):
C17H14N2
CAS Number:
Molecular Weight:
246.31
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.25
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Assay
≥98% (HPLC)
form
powder
storage temp.
2-8°C
SMILES string
C(c1c[nH]c2ccccc12)c3c[nH]c4ccccc34
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
InChI key
VFTRKSBEFQDZKX-UHFFFAOYSA-N
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Application
- 3,3′-Diindolylmethane inhibits Th17 cell differentiation via impairing IRF-7-mediated plasmacytoid dendritic cell activation in imiquimod-induced psoriasis mice.: The research indicates that 3,3′-Diindolylmethane can effectively inhibit Th17 cell differentiation, offering a potential therapeutic approach for treating psoriasis by targeting plasmacytoid dendritic cell pathways (Rasool et al., 2024).
- Protective effect of diindolylmethane-enriched dietary cabbage against doxorubicin-induced cardiotoxicity in mice.: This study highlights the cardioprotective effects of a diindolylmethane-enriched diet in mice, offering a dietary approach to mitigate the cardiotoxic effects of doxorubicin, a common chemotherapeutic agent (Natesh et al., 2024).
- Nanoformulated 3′-diindolylmethane modulates apoptosis, migration, and angiogenesis in breast cancer cells.: The investigation into nanoformulated 3′-diindolylmethane shows it significantly influences apoptosis, migration, and angiogenesis, suggesting its utility in targeted cancer therapies (Harakeh et al., 2024).
- Design, synthesis, and biological evaluation of 3,3′-diindolylmethane N-linked glycoconjugate as a leishmanial topoisomerase IB inhibitor with reduced cytotoxicity.: Research presents a synthesized glycoconjugate of 3,3′-Diindolylmethane as an effective inhibitor of leishmanial topoisomerase IB, demonstrating reduced cytotoxicity and potential as a therapeutic agent (Kour et al., 2023).
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Xueli Tian et al.
Cancer letters, 448, 20-30 (2019-02-05)
3,3'-Diindolymethane (DIM) is a dimeric condensation product of indole-3-carbinol (I3C) that is found in broccoli and cabbage. Although DIM has been reported to exhibit anticancer properties against multiple tumor types, the direct target proteins of DIM have not been fully
Yiwei Li et al.
Antioxidants & redox signaling, 19(2), 139-150 (2013-02-09)
Oxidative stress has been mechanistically linked with aging and chronic diseases, including cancer. In fact, oxidative stress status, chronic disease-related inflammation, and cancer occurred in the aging population are tightly correlated. It is well known that the activation of nuclear
Sanjeev Banerjee et al.
Mutation research, 728(1-2), 47-66 (2011-06-28)
Emerging evidence provide credible support in favor of the potential role of bioactive products derived from ingesting cruciferous vegetables such as broccoli, brussel sprouts, cauliflower and cabbage. Among many compounds, 3,3'-diindolylmethane (DIM) is generated in the acidic environment of the
Timothy E Hoffman et al.
Archives of toxicology, 93(3), 635-647 (2018-12-21)
The aryl hydrocarbon receptor (AhR) is a nuclear receptor that facilitates a wide transcriptional response and causes a variety of adaptive and maladaptive physiological functions. Such functions are entirely dependent on the type of ligand activating it, and therefore, the
Hanna Szaefer et al.
Nutrition and cancer, 67(8), 1342-1354 (2015-09-25)
Our previous studies showed the diversified effect of cabbage juices and indoles on the estrogen metabolism key enzymes (CYP1A1, CYP1A2, CYP1B1) in breast epithelial cells differing in ER status, i.e., in tumorigenic-MCF7, MDA-MB-231 and non-tumorigenic-MCF10A cells. The aim of the
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