3,3'-Diindolylmethane

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] The reputation of Brassica vegetables as healthy foods rests in part on the activities of diindolylmethane.[2][3] Limited data from clinical studies indicate that DIM may have some benefits for patients suffering from types of prostate cancer, however more studies are required.[4]

3,3'-Diindolylmethane
Names
IUPAC name
3,3′-methanediylbis(1H-indole)
Other names
3-(1H-Indol-3-ylmethyl)-1H-indole
3,3'-Methylenebis-1H-indole
DIM
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.124.716
UNII
Properties
C17H14N2
Molar mass 246.313 g·mol−1
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

Properties

Clinical data for the effects of DIM are limited, but because of potential anticancer properties, the National Cancer Institute of the United States has begun clinical trials of DIM as a therapeutic for numerous forms of cancer.[5][6] Much of the scientific interest is due to its action as a histone deacetylase inhibitor in vitro, specifically against HDAC1, HDAC2, and HDAC3.[7]

DIM is a metabolite of the Indole-3-carbinol (I3C), also known as Indolylmethanol, which has been shown to have some cancer-preventative effects and some anti-cancer properties.[8]

A study conducted in 2013 to research the use of DIM as a treatment to prevent or reduce the effects of acute radiation syndrome due to whole body exposure found that the compound may be useful in preventing or mitigating tissue damage due to partial body radiation exposure which occurs routinely during radiotherapy-based cancer treatment.[9]

Uses

At the present time, DIM is used to treat recurrent respiratory papillomatosis (RRP), a rare respiratory disease with tumors in the upper respiratory tracts caused by the human papilloma virus.[10] In a preliminary study on 64 women, it was well tolerated at the studied dose (2 mg/kg/day), showing some promising results as an immunostimulant against human papilloma virus infection of the cervix, but not at a statistically significant level.[11] In a subsequent double-blind, randomized, placebo-controlled study on 600 women, DIM in vivo had no effect on cytology regarding cervical dysplasia, a precancerous condition also caused by the human papilloma virus.[12]

DIM has been demonstrated to work synergistically with genistein (from soy), in causing apoptotic gene expression in breast cancer cells.[7]

Analogs

Some unnatural synthetic analogs were also prepared. For example, 1,1-bis(3'-indolyl)-1-(p-methoxyphenyl)methane is a Nur77 agonist.

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See also

References
  1. Rakel, D. (2007). "Ch. 57". Integrative Medicine (2nd ed.). Saunders.
  2. Gong, Y.; Sohn, H.; Xue, L.; Firestone, G. L.; Bjeldanes, L. F. (2006). "3,3'-Diindolylmethane is a novel mitochondrial H+-ATP synthase inhibitor that can induce p21Cip1/Waf1 expression by induction of oxidative stress in human breast cancer cells". Cancer Research. 66 (9): 4880–4887. doi:10.1158/0008-5472.CAN-05-4162. PMID 16651444.
  3. Acharya, A.; Das, I.; Singh, S.; Saha, T. (2010). "Chemopreventive properties of indole-3-carbinol, diindolylmethane and other constituents of cardamom against carcinogenesis". Recent Patents on Food, Nutrition & Agriculture. 2 (2): 166–177. doi:10.2174/1876142911002020166.
  4. "Diindolylmethane". Memorial Sloan Kettering Cancer Center. Retrieved 2019-09-03.
  5. Rogan, E. G. (2006). "The natural chemopreventive compound indole-3-carbinol: state of the science". In Vivo. 20 (2): 221–228. PMID 16634522.
  6. Kim, Y. S.; Milner, J. A. (2005). "Targets for indole-3-carbinol in cancer prevention". Journal of Nutritional Biochemistry. 16 (2): 65–73. doi:10.1016/j.jnutbio.2004.10.007. PMID 15681163.
  7. Rajendran, P; Ho, E; Williams, DE; Dashwood, RH (2011). "Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells". Clin Epigenetics. 3 (1): 4. doi:10.1186/1868-7083-3-4. PMC 3255482. PMID 22247744.
  8. "Indole-3-Carbinol". Memorial Sloan Kettering Cancer Center. Retrieved 2019-09-03.
  9. Fan, S.; Meng, Q.; Xu, J.; Jiao, Y.; Zhao, L.; Zhang, X.; Sarkar, F. H.; Brown, M. L.; Dritschilo, A. (2013-10-14). "DIM (3,3'-diindolylmethane) confers protection against ionizing radiation by a unique mechanism". Proceedings of the National Academy of Sciences. 110 (46): 18650–18655. doi:10.1073/pnas.1308206110. ISSN 0027-8424. PMC 3831962. PMID 24127581.
  10. Wiatrak, B. J. (2003). "Overview of recurrent respiratory papillomatosis". Current Opinion in Otolaryngology & Head and Neck Surgery. 11 (6): 433–441. doi:10.1097/00020840-200312000-00005. PMID 14631175.
  11. Del Priore, G.; Gudipudi, D. K.; Montemarano, N.; Restivo, A. M.; Malanowska-Stega, J.; Arslan, A. A. (2010). "Oral diindolylmethane (DIM): Pilot evaluation of a nonsurgical treatment for cervical dysplasia". Gynecologic Oncology. 116 (3): 464–467. doi:10.1016/j.ygyno.2009.10.060. PMID 19939441.
  12. Castañon, A.; Tristram, A.; Mesher, D.; Powell, N.; Beer, H.; Ashman, S.; Rieck, G.; Fielder, H.; Fiander, A.; Sasieni, P. (2011). "Effect of diindolylmethane supplementation on low-grade cervical cytological abnormalities: Double-blind, randomised, controlled trial". British Journal of Cancer. 106 (1): 45–52. doi:10.1038/bjc.2011.496. PMC 3251847. PMID 22075942.
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