3,3'-Diindolylmethane

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
1968-05-4
ChEBI CHEBI:50182
ChEMBL ChEMBL446452 YesY
ChemSpider 2963 YesY
Jmol 3D model Interactive image
Interactive image
PubChem 3071
Properties
C17H14N2
Molar mass 246.31 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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] The reputation of Brassica vegetables as healthy foods rests in part on the activities of diindolylmethane.[2][3]

Properties

DIM has the biological properties listed in the chart below. Because of its various 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.[4][5] Much of this is due to its action as a histone deacetylase inhibitor, specifically HDAC1, 2 and 3.[6]

Biological activities of 3,3'-diindolylmethane

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.[7] 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.[8] 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.[9]

Recent research suggests possible use as radioprotector and mitigator. Research shows a potential usage of DIM as a medical countermeasure to prevent or mitigate acute radiation syndrome due to whole body exposure. In this regard, DIM can be administered safely to humans and animals by oral or subcutaneous routes. DIM may also be useful in preventing or mitigating late normal tissue damage due to partial body radiation exposure during cancer treatment. DIM works, in part, by a mechanism distinct from other radioprotectors and mitigators involving stimulation of the DNA damage response, including DNA repair, and activation of cell survival signaling through the transcription factor NF-κB.[10]

DIM has been demonstrated to work synergystically with genistein (from soy), in causing apoptotic gene expression in breast cancer cells.[6]

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. ↑ Rogan, E. G. (2006). "The natural chemopreventive compound indole-3-carbinol: state of the science". In Vivo 20 (2): 221–228. PMID 16634522.
  5. ↑ 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.
  6. 1 2 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3255482/#B76
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ Saijun Fan, Qinghui Meng, Jiaying Xu, Yang Jiao, Lin Zhao, Xiaodong Zhang, Fazlul H. Sarkar, Milton L. Brown, Anatoly Dritschilo, and Eliot M. Rosen (2013). "DIM (3,3'-diindolylmethane) confers protection against ionizing radiation by a unique mechanism". PNAS: 18650–18655. doi:10.1073/pnas.1308206110.

External links

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