3,3'-Diindolylmethane

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3,3'-Diindolylmethane
IUPAC name 3-(1H-Indol-3-ylmethyl)-1H-indole
Other names 3,3'-Methylenebis-1H-indole
Identifiers
CAS number [1968-05-4]
PubChem 3071
SMILES C1=CC=C2C(=C1)C(=CN2)CC3=CNC4=CC=CC=C43
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
Properties
Molecular formula C17H14N2
Molar mass 246.307
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

3,3'-Diindolylmethane or DIM is derived from the digestion of indole-3-carbinol, found in Brassica vegetables such as broccoli and cauliflower.[citation needed] The reputation of Brassica vegetables as medicinal plants rests in part on the activities of diindolylmethane.[citation needed]

Contents

[edit] Properties

DIM has the biological properties listed in the chart below. Because of its various potent anti-cancer properties, the National Cancer Institute of the United States has begun clinical trials of DIM as a therapeutic for numerous forms of cancer.[citation needed] Due to its innate immune modulating properties (potentiation of Interferon-Gamma receptors and production),[citation needed] DIM is also under investigation as a treatment for a variety of viral infections and antibiotic resistant bacteria.[citation needed] As DIM has been demonstrated to synergize with Interferon-Gamma in the potentiation of the MHC-I Complex,[citation needed] it is currently also under investigation as an adjuvant to IFN-G treatment models for both cancer and viral infections such as HIV, HPV and Hepatitis.

Biological Activities of 3,3'-Diindolylmethane
Biological Activities of 3,3'-Diindolylmethane

[edit] Uses

DIM is currently used to treat Recurring Respiratory Papillomatosis, a rare respiratory disease with tumors in the upper respiratory tracts caused by the Human Papilloma Virus.[citation needed] DIM is additionally in Phase III clinical trials for Cervical dysplasia, a pre-cancerous condition also caused by the Human Papilloma Virus.[citation needed]

[edit] Clinical trials

DIM is in clinical trials as a treatment for numerous forms of cancer. It is being investigated as a potential treatment for a variety of viral and anti-biotic resistant bacterial infections, as well.

[edit] Further reading

  1. Hong, Chibo, Firestone, Gary L., Bjeldanes, Leonard F. (2000). 3,3'-Diindolylmethane(DIM), a dietary indole, has multiple cell suppressive effects on MCF-7, human breast cancer cells. Presented at the 40th Annual Meeting of American Society for Cell Biology, December 9-13, 2000, San Francisco. Availability verified July 30, 2005.
  2. DIM at the Comparative Toxicogenomics Database prototype. Availability verified July 29, 2005.
  3. Riby JE, Xue L, Chatterji U, Bjeldanes EL, Firestone GL, Bjeldanes LF. Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells. Molecular Pharmacology. 2006 Feb;69(2):430-9. Department of Nutritional Sciences and Toxicology, University of California, Berkeley, 94720-3104, USA.
  4. Xue L, Firestone GL, Bjeldanes LF. DIM stimulates IFNgamma gene expression in human breast cancer cells via the specific activation of JNK and p38 pathways. Department of Nutritional Sciences and Toxicology, University of California, 119 Morgan Hall, Berkeley, CA 94720-3104, USA. Oncogene. 2005 Mar 31;24(14):2343-53.
  5. Gong Y, Sohn H, Xue L, Firestone GL, Bjeldanes LF 3,3'-Diindolylmethane is a novel mitochondrial H(+)-ATP synthase inhibitor that can induce p21(Cip1/Waf1) expression by induction of oxidative stress in human breast cancer cells. Department of Nutritional Sciences and Toxicology, University of California, Berkeley, California 94720, USA. Cancer Research 2006 May 1;66(9):4880-7.
  6. K. McGuire, N. Ngoubilly, M. Neavyn, S. Lanza-Jacoby 3,3′-Diindolylmethane and Paclitaxel Act Synergistically to Promote Apoptosis in HER2/Neu Human Breast Cancer Cells. Journal of Surgical Research, 2006 May 15;132(2):208-13. Department of Surgery, Jefferson Medical College, Thomas Jefferson University, Philadelphia, Pennsylvania 19107.
  7. Staub RE, Onisko B, Bjeldanes LF Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells. Department of Nutritional Sciences and Toxicology, University of California, Berkeley, California 94720, USA. Chemical Research in Toxicology 2006 Mar;19(3):436-42
  8. Gong Y, Firestone GL, Bjeldanes LF 3,3'-diindolylmethane is a novel topoisomerase IIalpha catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells. Department of Nutritional Sciences and Toxicology, 119 Morgan Hall, University of California, Berkeley, CA 94720-3104, USA. Molecular Pharmacology 2006 Apr;69(4):1320-7. Epub 2005 Dec 29.
  9. Chang X, Firestone GL, Bjeldanes LF Inhibition of growth factor-induced Ras signaling in vascular endothelial cells and angiogenesis by 3,3'-diindolylmethane. Department of Nutritional Sciences and Toxicology, University of California, Berkeley, CA 94720, USA. Carcinogenesis 2006 Mar;27(3):541-50. Epub 2005 Sep 30.
  10. Chang X, Tou JC, Hong C, Kim HA, Riby JE, Firestone GL, Bjeldanes LF 3,3'-Diindolylmethane inhibits angiogenesis and the growth of transplantable human breast carcinoma in athymic mice. Department of Nutritional Sciences and Toxicology, University of California, Berkeley, CA 94720, USA. Carcinogenesis, 2005 Apr;26(4):771-8. Epub 2005 Jan 20.
  11. Leong H, Riby JE, Firestone GL, Bjeldanes LF Potent ligand-independent estrogen receptor activation by 3,3'-diindolylmethane is mediated by cross talk between the protein kinase A and mitogen-activated protein kinase signaling pathways. Department of Nutritional Sciences and Toxicology, University of California, Berkeley, California 94720, USA. Mol Endocrinol. 2004 Feb;18(2):291-302. Epub 2003 Nov 26.
  12. Firestone GL, Bjeldanes LF Indole-3-carbinol and 3-3'-diindolylmethane antiproliferative signaling pathways control cell-cycle gene transcription in human breast cancer cells by regulating promoter-Sp1 transcription factor interactions. Department of Molecular and Cell Biology and Cancer Research Laboratory, University of California at Berkeley, Berkeley, CA 94720-3200, USA. J Nutr. 2003 Jul;133(7 Suppl):2448S-2455S.
  13. Le HT, Schaldach CM, Firestone GL, Bjeldanes LF, Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells. Department of Nutritional Sciences and Toxicology, The University of California, Berkeley, California 94720-3104, USA. J Biol Chem. 2003 Jun 6;278(23):21136-45. Epub 2003 Mar 27.
  14. Hong C, Kim HA, Firestone GL, Bjeldanes LF 3,3'-Diindolylmethane (DIM) induces a G(1) cell cycle arrest in human breast cancer cells that is accompanied by Sp1-mediated activation of p21(WAF1/CIP1) expression. Department of Nutritional Sciences and Toxicology, University of California, Berkeley, CA 94720, USA. Carcinogenesis. 2002 Aug;23(8):1297-305.
  15. Hong C, Firestone GL, Bjeldanes LF Bcl-2 family-mediated apoptotic effects of 3,3'-diindolylmethane (DIM) in human breast cancer cells. Department of Nutritional Sciences and Toxicology, University of California, Berkeley 94720-3200, USA. Biochem Pharmacol. 2002 Mar 15;63(6):1085-97.
  16. Leong H, Firestone GL, Bjeldanes LF Cytostatic effects of 3,3'-diindolylmethane in human endometrial cancer cells result from an estrogen receptor-mediated increase in transforming growth factor-alpha expression. Department of Nutritional Sciences and Toxicology, University of California-Berkeley, Berkeley, CA 94720, USA. Carcinogenesis. 2001 Nov;22(11):1809-17.
  17. Riby JE, Chang GH, Firestone GL, Bjeldanes LF Ligand-independent activation of estrogen receptor function by 3, 3'-diindolylmethane in human breast cancer cells. Division of Nutritional Sciences and Toxicology, University of California, Berkeley, CA 94720, USA. Biochem Pharmacol. 2000 Jul 15;60(2):167-77.
  18. Chang YC, Riby J, Chang GH, Peng BC, Firestone G, Bjeldanes LF, Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3'-diindolylmethane, a major in vivo product of dietary indole-3-carbinol. Division of Nutritional Sciences and Toxicology, University of California, Berkeley 94720, USA. Biochem Pharmacol. 1999 Sep 1;58(5):825-34.
  19. Chen I, Safe S, Bjeldanes L. Indole-3-carbinol and diindolylmethane as aryl hydrocarbon (Ah) receptor agonists and antagonists in T47D human breast cancer cells. Veterinary Physiology and Pharmacology, Texas A&M University, College Station 77843-4466, USA. Biochem Pharmacol. 1996 Apr 26;51(8):1069-76.
  20. Stresser DM, Bjeldanes LF, Bailey GS, Williams DE The anticarcinogen 3,3'-diindolylmethane is an inhibitor of cytochrome P-450. Department of Food Science and Technology, Oregon State University, Corvallis 97331-6602, USA. J Biochem Toxicol. 1995 Aug;10(4):191-201.