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3,3'-Diindolylmethane

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3,3'-Diindolylmethane
Names
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)
223072
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.124.716 Edit this at Wikidata
EC Number
  • 606-355-3
UNII
  • 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 checkY
    Key: VFTRKSBEFQDZKX-UHFFFAOYSA-N checkY
  • InChI=1/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=1/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
    Key: VFTRKSBEFQDZKX-UHFFFAOYAU
  • c4ccc3c(Cc1c[nH]c2ccccc12)c[nH]c3c4
Properties
C17H14N2
Molar mass 246.313 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335, H413
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

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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

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References

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  1. ^ a b c d e "Indole-3-carbinol". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 July 2017. Retrieved 11 July 2022.
  2. ^ a b "Indole-3-Carbinol". Memorial Sloan Kettering Cancer Center. Retrieved 2019-09-03.
  3. ^ a b "3,3'-Diindolylmethane". PubChem, US National Library of Medicine. 9 July 2022. Retrieved 11 July 2022.
  4. ^ 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. PMC 3255482. PMID 22247744.
  5. ^ Andhika B. Mahardhika; et al. (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.
  6. ^ Paolo Tucci; et al. (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. hdl:2164/20232. PMC 9962283. PMID 36835033.
  7. ^ Yifat Baruch; et al. (6 June 2023). "3,3′-Diindolylmethane (DIM): A Potential Therapeutic Agent against Cariogenic Streptococcus mutans Biofilm". Antibiotics. 12 (6): 1017. doi:10.3390/antibiotics12061017. PMC 10295630. PMID 37370336.
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