View source for Chemistry:3,3'-Diindolylmethane

{{short description|Chemical compound}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477217074
| ImageFile=3,3'-Diindolylmethane.svg
| ImageSize=200px
| PIN=3,3′-Methylenedi(1''H''-indole)
| OtherNames=3-(1''H''-Indol-3-ylmethyl)-1''H''-indole<br />3,3′-Methylenebis-''1H''-indole<br />DIM
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=1968-05-4
| Beilstein = 223072
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2963
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 446452
| DrugBank = DB11875
| EINECS = 606-355-3
| IUPHAR_ligand = 11208
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SSZ9HQT61Z
| PubChem=3071
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50182
| SMILES = c4ccc3c(Cc1c[nH]c2ccccc12)c[nH]c3c4
| 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<!--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-->
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VFTRKSBEFQDZKX-UHFFFAOYSA-N
| InChI1 = 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
| InChIKey1 = VFTRKSBEFQDZKX-UHFFFAOYAU
  }}
|Section2={{Chembox Properties
| C=17 | H=14 | N=2
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335|413}}
| PPhrases = {{P-phrases|261|264|271|273|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}

'''3,3′-Diindolylmethane''' ('''DIM''') is a compound derived from the [[Biology:Digestion|digestion]] of [[Chemistry:Indole-3-carbinol|indole-3-carbinol]], found in [[Biology:Cruciferous vegetables|cruciferous vegetables]], such as [[Biology:Broccoli|broccoli]], [[Biology:Brussels sprout|Brussels sprout]]s, [[Biology:Cabbage|cabbage]] and kale.<ref name="lpi">{{cite web | title = Indole-3-carbinol|url=https://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/indole-3-carbinol|publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University|date=1 July 2017|accessdate=11 July 2022}}</ref> It and its parent compound {{ndash}} [[Chemistry:Indole-3-carbinol|indole-3-carbinol]] {{ndash}} are under laboratory research to determine their possible biological properties, particularly in anti-cancer mechanisms.<ref name=lpi/><ref name=msk/><ref name="pubchem">{{cite web |title=3,3'-Diindolylmethane |url=https://pubchem.ncbi.nlm.nih.gov/compound/3071 |publisher=PubChem, US National Library of Medicine |access-date=11 July 2022 |date=9 July 2022}}</ref> DIM is sold as a dietary supplement.<ref name=lpi/>

==Properties==
[[In vitro]], DIM has action as a [[Biology:Histone deacetylase inhibitor|histone deacetylase inhibitor]],<ref name=lpi/> specifically against [[Biology:HDAC1|HDAC1]], HDAC2, and [[Biology:HDAC3|HDAC3]].<ref name="dietaryncbi">{{cite journal | pmc = 3255482 | pmid=22247744 | doi=10.1186/1868-7083-3-4 | volume=3 | issue=1 | title=Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells | year=2011 | journal= Clinical Epigenetics| pages=4 | last1 = Rajendran | first1 = P | last2 = Ho | first2 = E | last3 = Williams | first3 = DE | last4 = Dashwood | first4 = RH | doi-access=free }}</ref> DIM is a [[Biology:Metabolite|metabolite]] of [[Chemistry:Indole-3-carbinol|indole-3-carbinol]].<ref name=lpi/><ref name="msk">{{Cite web|url=https://www.mskcc.org/cancer-care/integrative-medicine/herbs/indole-3-carbinol|title=Indole-3-Carbinol|website=Memorial Sloan Kettering Cancer Center|language=en|access-date=2019-09-03}}</ref><ref name=pubchem/> DIM was found to be a mild cannabinoid agonist with low binding affinity for both CB1 and CB2.<ref>{{cite journal |author=Andhika B. Mahardhika |display-authors=et. al. |title=Design, synthesis, and structure–activity relationships of diindolylmethane derivatives as cannabinoid CB2 receptor agonists |journal= Archiv der Pharmazie|date=March 2023 |volume=356 |issue=3 |pages=e2200493 |doi=10.1002/ardp.202200493|pmid=36437108 |doi-access=free }}</ref><ref>{{cite journal |author=Paolo Tucci |display-authors=et. al. |title=The Plant Derived 3-3′-Diindolylmethane (DIM) Behaves as CB2 Receptor Agonist in Prostate Cancer Cellular Models |journal=International Journal of Molecular Sciences |date=2023 |volume=24 |issue=4 |page=3620 |doi=10.3390/ijms24043620|pmid=36835033 |pmc=9962283 |hdl=2164/20232 |hdl-access=free |doi-access=free }}</ref>

Researchers from [[Organization:Ben-Gurion University of the Negev|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%. <ref>{{cite journal |author=Yifat Baruch |display-authors=et. al. |title=3,3′-Diindolylmethane (DIM): A Potential Therapeutic Agent against Cariogenic ''Streptococcus mutans'' Biofilm |journal=  Antibiotics|date=6 June 2023 |volume=12 |issue=6 |page=1017 |doi=10.3390/antibiotics12061017|pmid=37370336 |pmc=10295630 |doi-access=free }}</ref>

==See also==
* [[Chemistry:Glucobrassicin|Glucobrassicin]], precursor to indole-3-carbinol
* Phytochemicals

==References==
{{reflist}}

== External links ==
* [http://www.diindolylmethane.org/ Diindolylmethane Information Resource Center], University of California-Berkeley

{{HDAC inhibitors}}

{{DEFAULTSORT:Diindolylmethane, 3, 3'-}}
[[Category:Indoles]]
[[Category:Histone deacetylase inhibitors]]

{{Sourceattribution|3,3'-Diindolylmethane}}