3,3'-Diindolylmethane
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| Names | |
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| IUPAC name
3,3′-methanediylbis(1H-indole)
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| Other names
3-(1H-Indol-3-ylmethyl)-1H-indole
3,3'-Methylenebis-1H-indole DIM | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.124.716 |
PubChem CID
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| 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). | |
 verify (what is   ?)
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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][dead link]
Properties[edit]
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][needs update] 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[edit]
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]
Analogs[edit]
Some unnatural synthetic analogs were also prepared. For example, 1,1-bis(3'-indolyl)-1-(p-methoxyphenyl)methane is a Nur77 agonist.[citation needed]
See also[edit]
- Glucobrassicin, precursor to indole-3-carbinol
- Phytochemicals
References[edit]
- ^ Rakel, D. (2007). "Ch. 57". Integrative Medicine (2nd ed.). Saunders.[page needed]
- ^ 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.
- ^ 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.
- ^ Rogan, E. G. (2006). "The natural chemopreventive compound indole-3-carbinol: state of the science". In Vivo. 20 (2): 221–228. PMID 16634522.
- ^ 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.
- ^ a b 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.
- ^ 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.
- ^ 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.
- ^ 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.
External links[edit]
