Chemistry:3,3'-Diindolylmethane
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| Names | |
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| Preferred IUPAC name
3,3′-Methylenedi(1H-indole) | |
| Other names
3-(1H-Indol-3-ylmethyl)-1H-indole
3,3′-Methylenebis-1H-indole DIM | |
| Identifiers | |
3D model (JSmol)
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| 223072 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
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PubChem CID
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| UNII | |
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| Properties | |
| C17H14N2 | |
| Molar mass | 246.313 g·mol−1 |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | Warning |
| H315, H319, H335, H413 | |
| P261, P264, P271, P273, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
3,3′-Diindolylmethane (DIM) is a compound derived from the digestion of indole-3-carbinol, found in cruciferous vegetables, such as broccoli, Brussels sprouts, cabbage and kale.[1] It and its parent compound – indole-3-carbinol – are under laboratory research to determine their possible biological properties, particularly in anti-cancer mechanisms.[1][2][3] DIM is sold as a dietary supplement.[1]
Properties
In vitro, DIM has action as a histone deacetylase inhibitor,[1] specifically against HDAC1, HDAC2, and HDAC3.[4] DIM is a metabolite of indole-3-carbinol.[1][2][3] DIM was found to be a mild cannabinoid agonist with low binding affinity for both CB1 and CB2.[5][6]
Researchers from Ben-Gurion University of the Negev, in collaboration with teams from Sichuan University and the National University of Singapore, have identified that 3,3′-Diindolylmethane (DIM) – a naturally occurring molecule also referred to as bisindole – can reduce biofilms responsible for plaque and cavities by a remarkable 90%. [7]
See also
- Glucobrassicin, precursor to indole-3-carbinol
- Phytochemicals
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "Indole-3-carbinol". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 July 2017. https://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/indole-3-carbinol. Retrieved 11 July 2022.
- ↑ 2.0 2.1 "Indole-3-Carbinol" (in en). https://www.mskcc.org/cancer-care/integrative-medicine/herbs/indole-3-carbinol.
- ↑ 3.0 3.1 "3,3'-Diindolylmethane". PubChem, US National Library of Medicine. 9 July 2022. https://pubchem.ncbi.nlm.nih.gov/compound/3071.
- ↑ Rajendran, P; Ho, E; Williams, DE; Dashwood, RH (2011). "Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells". Clinical Epigenetics 3 (1): 4. doi:10.1186/1868-7083-3-4. PMID 22247744.
- ↑ Andhika B. Mahardhika (March 2023). "Design, synthesis, and structure–activity relationships of diindolylmethane derivatives as cannabinoid CB2 receptor agonists". Archiv der Pharmazie 356 (3): e2200493. doi:10.1002/ardp.202200493. PMID 36437108.
- ↑ Paolo Tucci (2023). "The Plant Derived 3-3′-Diindolylmethane (DIM) Behaves as CB2 Receptor Agonist in Prostate Cancer Cellular Models". International Journal of Molecular Sciences 24 (4): 3620. doi:10.3390/ijms24043620. PMID 36835033.
- ↑ Yifat Baruch (6 June 2023). "3,3′-Diindolylmethane (DIM): A Potential Therapeutic Agent against Cariogenic Streptococcus mutans Biofilm". Antibiotics 12 (6): 1017. doi:10.3390/antibiotics12061017. PMID 37370336.
External links
- Diindolylmethane Information Resource Center, University of California-Berkeley
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