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 | |
CAS Number |
|
3D model (JSmol) |
|
Beilstein Reference | 223072 |
ChEBI |
|
ChEMBL |
|
ChemSpider |
|
DrugBank |
|
ECHA InfoCard | 100.124.716 |
EC Number |
|
IUPHAR/BPS |
|
PubChem CID |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
Properties | |
Chemical formula | C17H14N2 |
Molar mass | 246.313 g·mol−1 |
Hazards | |
GHS labelling: | |
Pictograms | |
Warning | |
Hazard statements | H315, H319, H335, H413 |
Precautionary statements | 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 YN ?) 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
- ^ a b c d e "Indole-3-carbinol". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 July 2017. Retrieved 11 July 2022.
- ^ a b "Indole-3-Carbinol". Memorial Sloan Kettering Cancer Center. Retrieved 2019-09-03.
- ^ a b "3,3'-Diindolylmethane". PubChem, US National Library of Medicine. 9 July 2022. Retrieved 11 July 2022.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
External links
- Diindolylmethane Information Resource Center, University of California-Berkeley
- v
- t
- e
- 3,3'-Diindolylmethane
- β-Hydroxybutyric acid (β-hydroxybutyrate)
- Abexinostat
- Acetoacetic acid (acetoacetate)
- Allyl mercaptan
- Apicidin
- Belinostat
- Butyric acid (butyrate)
- Capsaicin
- Citarinostat
- Curcumin
- Diallyl disulfide
- Entinostat
- Fimepinostat
- Givinostat
- Indole-3-carbinol
- Kevetrin
- Martinostat
- Mocetinostat
- Niacinamide
- Panobinostat
- Parthenolide
- Phenylbutyrate
- Pracinostat
- Quisinostat
- Resminostat
- Romidepsin
- Scriptaid
- Sodium butyrate
- Sodium oxybate (GHB sodium)
- Sodium phenylbutyrate
- Sodium valproate
- Sulforaphane
- Trapoxin B
- Trichostatin A
- Tucidinostat
- Valnoctamide
- Valproic acid (valproate)
- Valproate pivoxil
- Valproate semisodium
- Valpromide
- Vorinostat (SAHA)