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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.124.716
UNII
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

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.[4][5] Much of the scientific interest is due to its action as a histone deacetylase inhibitor in vitro, specifically against HDAC1, HDAC2, and HDAC3.[6]

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]

DIM has been demonstrated to work synergistically 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 Rajendran, P; Ho, E; Williams, DE; Dashwood, RH (2011). "Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells". Clin Epigenetics. 3: 4. doi:10.1186/1868-7083-3-4. PMC 3255482. PMID 22247744.
  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.
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