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3,3'-Diindolylmethane
3,3'-Diindolylmethane.svg
IUPAC name
Other names 3-(1H-Indol-3-ylmethyl)-1H-indole
3,3'-Methylenebis-1H-indole
DIM
Identifiers
CAS number 1968-05-4
PubChem 3071
SMILES
InChI
Properties
Molecular formula C17H14N2
Molar mass 246.31 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3,3′-Diindolylmethane or DIM is an anticarcinogen compound derived from the digestion of indole-3-carbinol, found in Brassica vegetables such as broccoli and cauliflower. The reputation of Brassica vegetables as medicinal plants rests in part on the activities of diindolylmethane.

Contents

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. Due to its innate immune modulating properties (potentiation of Interferon-Gamma receptors and production), DIM is also under investigation as a treatment for a variety of viral infections and antibiotic resistant bacteria. As DIM has been demonstrated to synergize with Interferon-Gamma in the potentiation of the MHC-I Complex, 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

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. DIM is additionally in Phase III clinical trials for Cervical dysplasia, a pre-cancerous condition also caused by the Human Papilloma Virus.

Clinical trials

A search of internet websites on November 7, 2009 of both the National Cancer Institute (United States) and registered cancer trials (United States, at http://clinicaltrials.gov/ct2/results?intr=%22Indole%22) shows five cancer treatment trials of 3,3'-diindolylmethane (DIM). Four of these trials have been completed or are not currently recruiting. No study results are posted for these four trials. The fifth trial is ongoing and recruiting subjects. It is stated "To measure the level of diindolylmethane in prostate tissue after treatment with oral microencapsulated diindolylmethane (B-DIM) in patients with stage I or II adenocarcinoma of the prostate undergoing radical prostatectomy." The trial sponsors include the Barbara Ann Karmanos Cancer Institute (Detroit, MI) and the National Cancer Institute. It is currently enrolling patients at three sites. It is said that DIM is also being investigated as a potential treatment for a variety of viral and anti-biotic resistant bacterial infections, as well.

See also

Bibliography

  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 (February 2006). "Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells". Mol Pharmacol. 69 (2): 430–9. doi:10.1124/mol.105.017053. PMID 16267208.  
  4. Xue L, Firestone GL, Bjeldanes LF (March 2005). "DIM stimulates IFNgamma gene expression in human breast cancer cells via the specific activation of JNK and p38 pathways". Oncogene 24 (14): 2343–53. doi:10.1038/sj.onc.1208434. PMID 15735741.  
  5. Gong Y, Sohn H, Xue L, Firestone GL, Bjeldanes LF (May 2006). "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". Cancer Res. 66 (9): 4880–7. doi:10.1158/0008-5472.CAN-05-4162. PMID 16651444.  
  6. McGuire KP, Ngoubilly N, Neavyn M, Lanza-Jacoby S (May 2006). "3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells". J Surg Res. 132 (2): 208–13. doi:10.1016/j.jss.2006.02.008. PMID 16580691.  
  7. Staub RE, Onisko B, Bjeldanes LF (March 2006). "Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells". Chem Res Toxicol. 19 (3): 436–42. doi:10.1021/tx050325z. PMID 16544949.  
  8. Gong Y, Firestone GL, Bjeldanes LF (April 2006). "3,3'-diindolylmethane is a novel topoisomerase IIalpha catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells". Mol Pharmacol. 69 (4): 1320–7. doi:10.1124/mol.105.018978. PMID 16385077.  
  9. Chang X, Firestone GL, Bjeldanes LF (March 2006). "Inhibition of growth factor-induced Ras signaling in vascular endothelial cells and angiogenesis by 3,3'-diindolylmethane". Carcinogenesis 27 (3): 541–50. doi:10.1093/carcin/bgi230. PMID 16199440.  
  10. Chang X, Tou JC, Hong C, et al. (April 2005). "3,3'-Diindolylmethane inhibits angiogenesis and the growth of transplantable human breast carcinoma in athymic mice". Carcinogenesis 26 (4): 771–8. doi:10.1093/carcin/bgi018. PMID 15661811.  
  11. Leong H, Riby JE, Firestone GL, Bjeldanes LF (February 2004). "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". Mol Endocrinol. 18 (2): 291–302. doi:10.1210/me.2003-0196. PMID 14645498.  
  12. Firestone GL, Bjeldanes LF (1 July 2003). "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". J Nutr. 133 (7 Suppl): 2448S–55S. PMID 12840223. http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=12840223.  
  13. Le HT, Schaldach CM, Firestone GL, Bjeldanes LF (June 2003). "Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells". J Biol Chem. 278 (23): 21136–45. doi:10.1074/jbc.M300588200. PMID 12665522.  
  14. Hong C, Kim HA, Firestone GL, Bjeldanes LF (August 2002). "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". Carcinogenesis 23 (8): 1297–305. doi:10.1093/carcin/23.8.1297. PMID 12151347. http://carcin.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12151347.  
  15. Hong C, Firestone GL, Bjeldanes LF (March 2002). "Bcl-2 family-mediated apoptotic effects of 3,3'-diindolylmethane (DIM) in human breast cancer cells". Biochem Pharmacol. 63 (6): 1085–97. doi:10.1016/S0006-2952(02)00856-0. PMID 11931841. http://linkinghub.elsevier.com/retrieve/pii/S0006295202008560.  
  16. Leong H, Firestone GL, Bjeldanes LF (November 2001). "Cytostatic effects of 3,3'-diindolylmethane in human endometrial cancer cells result from an estrogen receptor-mediated increase in transforming growth factor-alpha expression". Carcinogenesis 22 (11): 1809–17. doi:10.1093/carcin/22.11.1809. PMID 11698343. http://carcin.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11698343.  
  17. Riby JE, Chang GH, Firestone GL, Bjeldanes LF (July 2000). "Ligand-independent activation of estrogen receptor function by 3, 3'-diindolylmethane in human breast cancer cells". Biochem Pharmacol. 60 (2): 167–77. doi:10.1016/S0006-2952(00)00307-5. PMID 10825461. http://linkinghub.elsevier.com/retrieve/pii/S0006-2952(00)00307-5.  
  18. Chang YC, Riby J, Chang GH, Peng BC, Firestone G, Bjeldanes LF (September 1999). "Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3'-diindolylmethane, a major in vivo product of dietary indole-3-carbinol". Biochem Pharmacol. 58 (5): 825–34. doi:10.1016/S0006-2952(99)00165-3. PMID 10449193. http://linkinghub.elsevier.com/retrieve/pii/S0006295299001653.  
  19. Chen I, Safe S, Bjeldanes L (April 1996). "Indole-3-carbinol and diindolylmethane as aryl hydrocarbon (Ah) receptor agonists and antagonists in T47D human breast cancer cells". Biochem Pharmacol. 51 (8): 1069–76. doi:10.1016/0006-2952(96)00060-3. PMID 8866829. http://linkinghub.elsevier.com/retrieve/pii/0006-2952(96)00060-3.  
  20. Stresser DM, Bjeldanes LF, Bailey GS, Williams DE (August 1995). "The anticarcinogen 3,3'-diindolylmethane is an inhibitor of cytochrome P-450". J Biochem Toxicol. 10 (4): 191–201. doi:10.1002/jbt.2570100403. PMID 8568833.  

3,3'-Diindolylmethane
File:3,3'
IUPAC name
3,3′-methanediylbis(1H-indole)
Other names
3-(1H-Indol-3-ylmethyl)-1H-indole
3,3'-Methylenebis-1H-indole
DIM
Identifiers
CAS number 1968-05-4
PubChem 3071
SMILES
InChI
Properties
Molecular formula C17H14N2
Molar mass 246.31 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

Contents

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.

Uses

At the present time, DIM is 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] In addition, DIM is in Phase III clinical trials for Cervical dysplasia, a pre-cancerous condition also caused by the Human Papilloma Virus.[citation needed]

Clinical trials

A search of internet websites on November 7, 2009 of both the National Cancer Institute (United States) and registered cancer trials (United States, at http://clinicaltrials.gov/ct2/results?intr=%22Indole%22) shows five cancer treatment trials of 3,3'-diindolylmethane (DIM). Four of these trials have been completed or are not currently recruiting. No study results are posted for these four trials. The fifth trial is ongoing and recruiting subjects. It is stated "To measure the level of diindolylmethane in prostate tissue after treatment with diindolylmethane (DIM) in patients with stage I or II adenocarcinoma of the prostate undergoing radical prostatectomy." The trial sponsors include the Barbara Ann Karmanos Cancer Institute (Detroit, MI) and the National Cancer Institute. It is currently enrolling patients at three sites. It is said that DIM is also being investigated as a potential treatment for a variety of viral and antibiotic-resistant bacterial infections, as well.

See also

Bibliography

  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 (February 2006). [Expression error: Unexpected < operator "Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells"]. Mol Pharmacol. 69 (2): 430–9. doi:10.1124/mol.105.017053. PMID 16267208. 
  4. Xue L, Firestone GL, Bjeldanes LF (March 2005). [Expression error: Unexpected < operator "DIM stimulates IFNgamma gene expression in human breast cancer cells via the specific activation of JNK and p38 pathways"]. Oncogene 24 (14): 2343–53. doi:10.1038/sj.onc.1208434. PMID 15735741. 
  5. Gong Y, Sohn H, Xue L, Firestone GL, Bjeldanes LF (May 2006). [Expression error: Unexpected < operator "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"]. Cancer Res. 66 (9): 4880–7. doi:10.1158/0008-5472.CAN-05-4162. PMID 16651444. 
  6. McGuire KP, Ngoubilly N, Neavyn M, Lanza-Jacoby S (May 2006). [Expression error: Unexpected < operator "3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells"]. J Surg Res. 132 (2): 208–13. doi:10.1016/j.jss.2006.02.008. PMID 16580691. 
  7. Staub RE, Onisko B, Bjeldanes LF (March 2006). [Expression error: Unexpected < operator "Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells"]. Chem Res Toxicol. 19 (3): 436–42. doi:10.1021/tx050325z. PMID 16544949. 
  8. Gong Y, Firestone GL, Bjeldanes LF (April 2006). [Expression error: Unexpected < operator "3,3'-diindolylmethane is a novel topoisomerase IIalpha catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells"]. Mol Pharmacol. 69 (4): 1320–7. doi:10.1124/mol.105.018978. PMID 16385077. 
  9. Chang X, Firestone GL, Bjeldanes LF (March 2006). [Expression error: Unexpected < operator "Inhibition of growth factor-induced Ras signaling in vascular endothelial cells and angiogenesis by 3,3'-diindolylmethane"]. Carcinogenesis 27 (3): 541–50. doi:10.1093/carcin/bgi230. PMID 16199440. 
  10. Chang X, Tou JC, Hong C, et al. (April 2005). [Expression error: Unexpected < operator "3,3'-Diindolylmethane inhibits angiogenesis and the growth of transplantable human breast carcinoma in athymic mice"]. Carcinogenesis 26 (4): 771–8. doi:10.1093/carcin/bgi018. PMID 15661811. 
  11. Leong H, Riby JE, Firestone GL, Bjeldanes LF (February 2004). [Expression error: Unexpected < operator "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"]. Mol Endocrinol. 18 (2): 291–302. doi:10.1210/me.2003-0196. PMID 14645498. 
  12. Firestone GL, Bjeldanes LF (1 July 2003). "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". J Nutr. 133 (7 Suppl): 2448S–55S. PMID 12840223. http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=12840223. 
  13. Le HT, Schaldach CM, Firestone GL, Bjeldanes LF (June 2003). [Expression error: Unexpected < operator "Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells"]. J Biol Chem. 278 (23): 21136–45. doi:10.1074/jbc.M300588200. PMID 12665522. 
  14. Hong C, Kim HA, Firestone GL, Bjeldanes LF (August 2002). "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". Carcinogenesis 23 (8): 1297–305. doi:10.1093/carcin/23.8.1297. PMID 12151347. http://carcin.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12151347. 
  15. Hong C, Firestone GL, Bjeldanes LF (March 2002). "Bcl-2 family-mediated apoptotic effects of 3,3'-diindolylmethane (DIM) in human breast cancer cells". Biochem Pharmacol. 63 (6): 1085–97. doi:10.1016/S0006-2952(02)00856-0. PMID 11931841. http://linkinghub.elsevier.com/retrieve/pii/S0006295202008560. 
  16. Leong H, Firestone GL, Bjeldanes LF (November 2001). "Cytostatic effects of 3,3'-diindolylmethane in human endometrial cancer cells result from an estrogen receptor-mediated increase in transforming growth factor-alpha expression". Carcinogenesis 22 (11): 1809–17. doi:10.1093/carcin/22.11.1809. PMID 11698343. http://carcin.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11698343. 
  17. Riby JE, Chang GH, Firestone GL, Bjeldanes LF (July 2000). "Ligand-independent activation of estrogen receptor function by 3, 3'-diindolylmethane in human breast cancer cells". Biochem Pharmacol. 60 (2): 167–77. doi:10.1016/S0006-2952(00)00307-5. PMID 10825461. http://linkinghub.elsevier.com/retrieve/pii/S0006-2952(00)00307-5. 
  18. Chang YC, Riby J, Chang GH, Peng BC, Firestone G, Bjeldanes LF (September 1999). "Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3'-diindolylmethane, a major in vivo product of dietary indole-3-carbinol". Biochem Pharmacol. 58 (5): 825–34. doi:10.1016/S0006-2952(99)00165-3. PMID 10449193. http://linkinghub.elsevier.com/retrieve/pii/S0006295299001653. 
  19. Chen I, Safe S, Bjeldanes L (April 1996). "Indole-3-carbinol and diindolylmethane as aryl hydrocarbon (Ah) receptor agonists and antagonists in T47D human breast cancer cells". Biochem Pharmacol. 51 (8): 1069–76. doi:10.1016/0006-2952(96)00060-3. PMID 8866829. http://linkinghub.elsevier.com/retrieve/pii/0006-2952(96)00060-3. 
  20. Stresser DM, Bjeldanes LF, Bailey GS, Williams DE (August 1995). [Expression error: Unexpected < operator "The anticarcinogen 3,3'-diindolylmethane is an inhibitor of cytochrome P-450"]. J Biochem Toxicol. 10 (4): 191–201. doi:10.1002/jbt.2570100403. PMID 8568833. 

Diindolylmethane Immune Activation Data Center

Diindolylmethane Information Resource Center

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