Diindolymetano, Diidolylméthane, DIM, 3,3'-Diindolylmethane.<br/><br/>


Overview Information

Diindolylmethane is formed in the body from plant substances contained in “cruciferous” vegetables such as cabbage, Brussels sprouts, cauliflower, and broccoli. Scientists think these vegetables may help to protect the body against cancer because they contain diindolylmethane and a related chemical called indole-3-carbinol.

Diindolylmethane is used for preventing breast, uterine, and colorectal cancer. It is also used to prevent an enlarged prostate (benign prostatic hypertrophy, BPH) and treat premenstrual syndrome (PMS).

How does it work?

Diindolylmethane might act like estrogen in the body, but there is evidence that under certain circumstances it might also block estrogen effects.


Uses & Effectiveness?

Insufficient Evidence for

More evidence is needed to rate the effectiveness of diindolylmethane for these uses.

Side Effects

Side Effects & Safety

Diindolylmethane is LIKELY SAFE when consumed in the small amounts found in foods. A typical diet supplies 2-24 mg of diindolylmethane. It is POSSIBLY SAFE for most people when taken by mouth short-term for medicinal purposes. Taking larger doses of diindolylmethane is POSSIBLY UNSAFE. Taking 600 mg of diindolylmethane daily has been reported to lower sodium levels in some people.

Special Precautions & Warnings:

Pregnancy and breast-feeding: Diindolylmethane is LIKELY SAFE when consumed in the small amounts found in foods. But don’t take larger amounts. Not enough is known about the safety of larger amounts during pregnancy and breast-feeding.

Children: Diindolylmethane is LIKELY SAFE when consumed in the small amounts found in foods. But don’t give children larger amounts. Not enough is known about the safety of larger amounts of diindolylmethane when given to children.

Hormone-sensitive conditions such as breast cancer, uterine cancer, ovarian cancer, endometriosis, or uterine fibroids: Diindolylmethane might act like estrogen, so there is some concern that it might make hormone-sensitive conditions worse. These conditions include breast, uterine, and ovarian cancer; endometriosis; and uterine fibroids. However, developing research also suggests that diindolylmethane might work against estrogen and could possibly be protective against hormone-dependent cancers. But stay on the safe side. Until more is known, don’t use diindolylmethane if you have a hormone-sensitive condition.



Minor Interaction

Be watchful with this combination

  • Medications changed by the liver (Cytochrome P450 1A2 (CYP1A2) substrates) interacts with DIINDOLYLMETHANE

    Some medications are changed and broken down by the liver.<br><nb>Diindolylmethane might increase how quickly the liver breaks down some medications. Taking diindolylmethane along with some medications that are changed by the liver can decrease the effectiveness of some medications. Before taking diindolylmethane talk to your healthcare provider if you take any medications that are changed by the liver.<br><nb>Some of these medications that are changed by the liver include clozapine (Clozaril), cyclobenzaprine (Flexeril), fluvoxamine (Luvox), haloperidol (Haldol), imipramine (Tofranil), mexiletine (Mexitil), olanzapine (Zyprexa), pentazocine (Talwin), propranolol (Inderal), tacrine (Cognex), theophylline, zileuton (Zyflo), zolmitriptan (Zomig), and others.



The appropriate dose of diindolylmethane depends on several factors such as the user's age, health, and several other conditions. At this time there is not enough scientific information to determine an appropriate range of doses for diindolylmethane. Keep in mind that natural products are not always necessarily safe and dosages can be important. Be sure to follow relevant directions on product labels and consult your pharmacist or physician or other healthcare professional before using.

View References


  • Reed, G. A., Sunega, J. M., Sullivan, D. K., Gray, J. C., Mayo, M. S., Crowell, J. A., and Hurwitz, A. Single-dose pharmacokinetics and tolerability of absorption-enhanced 3,3'-diindolylmethane in healthy subjects. Cancer Epidemiol.Biomarkers Prev. 2008;17(10):2619-2624. View abstract.
  • Renwick, A. B., Mistry, H., Barton, P. T., Mallet, F., Price, R. J., Beamand, J. A., and Lake, B. G. Effect of some indole derivatives on xenobiotic metabolism and xenobiotic-induced toxicity in cultured rat liver slices. Food Chem.Toxicol. 1999;37(6):609-618. View abstract.
  • Riby, J. E., Firestone, G. L., and Bjeldanes, L. F. 3,3'-diindolylmethane reduces levels of HIF-1alpha and HIF-1 activity in hypoxic cultured human cancer cells. Biochem.Pharmacol. 5-1-2008;75(9):1858-1867. View abstract.
  • Riby, J. E., Xue, L., Chatterji, U., Bjeldanes, E. L., Firestone, G. L., and Bjeldanes, L. F. Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells. Mol.Pharmacol. 2006;69(2):430-439. View abstract.
  • Rogan, E. G. The natural chemopreventive compound indole-3-carbinol: state of the science. In Vivo 2006;20(2):221-228. View abstract.
  • Roy, A., BoseDasgupta, S., Ganguly, A., Jaisankar, P., and Majumder, H. K. Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane. Antimicrob.Agents Chemother. 2009;53(6):2589-2598. View abstract.
  • Roy, A., Ganguly, A., BoseDasgupta, S., Das, B. B., Pal, C., Jaisankar, P., and Majumder, H. K. Mitochondria-dependent reactive oxygen species-mediated programmed cell death induced by 3,3'-diindolylmethane through inhibition of F0F1-ATP synthase in unicellular protozoan parasite Leishmania donovani. Mol.Pharmacol. 2008;74(5):1292-1307. View abstract.
  • Sanderson, J. T., Slobbe, L., Lansbergen, G. W., Safe, S., and van den Berg, M. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells. Toxicol.Sci. 2001;61(1):40-48. View abstract.
  • Sarkar, F. H. and Li, Y. Cell signaling pathways altered by natural chemopreventive agents. Mutat.Res 11-2-2004;555(1-2):53-64. View abstract.
  • Sarkar, F. H. and Li, Y. Indole-3-carbinol and prostate cancer. J.Nutr. 2004;134(12 Suppl):3493S-3498S. View abstract.
  • Sarkar, F. H., Li, Y., Wang, Z., and Kong, D. Cellular signaling perturbation by natural products. Cell Signal. 2009;21(11):1541-1547. View abstract.
  • Sarkar, F. H., Li, Y., Wang, Z., and Kong, D. The role of nutraceuticals in the regulation of Wnt and Hedgehog signaling in cancer. Cancer Metastasis Rev. 2010;29(3):383-394. View abstract.
  • Sarkar, F. H., Li, Y., Wang, Z., Kong, D., and Ali, S. Implication of microRNAs in drug resistance for designing novel cancer therapy. Drug Resist.Updat. 2010;13(3):57-66. View abstract.
  • Sasieni, P. Chemoprevention of cervical cancer. Best.Pract.Res.Clin.Obstet.Gynaecol. 2006;20(2):295-305. View abstract.
  • Savino, J. A., III, Evans, J. F., Rabinowitz, D., Auborn, K. J., and Carter, T. H. Multiple, disparate roles for calcium signaling in apoptosis of human prostate and cervical cancer cells exposed to diindolylmethane. Mol.Cancer Ther. 2006;5(3):556-563. View abstract.
  • Sepkovic, D. W., Bradlow, H. L., and Bell, M. Quantitative determination of 3,3'-diindolylmethane in urine of individuals receiving indole-3-carbinol. Nutr.Cancer 2001;41(1-2):57-63. View abstract.
  • Sepkovic, D. W., Stein, J., Carlisle, A. D., Ksieski, H. B., Auborn, K., and Bradlow, H. L. Diindolylmethane inhibits cervical dysplasia, alters estrogen metabolism, and enhances immune response in the K14-HPV16 transgenic mouse model. Cancer Epidemiol.Biomarkers Prev. 2009;18(11):2957-2964. View abstract.
  • Shilling, A. D., Carlson, D. B., Katchamart, S., and Williams, D. E. 3,3'-diindolylmethane, a major condensation product of indole-3-carbinol, is a potent estrogen in the rainbow trout. Toxicol.Appl.Pharmacol. 2-1-2001;170(3):191-200. View abstract.
  • Smith, S., Sepkovic, D., Bradlow, H. L., and Auborn, K. J. 3,3'-Diindolylmethane and genistein decrease the adverse effects of estrogen in LNCaP and PC-3 prostate cancer cells. J.Nutr. 2008;138(12):2379-2385. View abstract.
  • Smith, T. K., Lund, E. K., Clarke, R. G., Bennett, R. N., and Johnson, I. T. Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro. J.Agric.Food Chem. 5-18-2005;53(10):3895-3901. View abstract.
  • Sreevalsan, S., Jutooru, I., Chadalapaka, G., Walker, M., and Safe, S. 1,1-Bis(3'-indolyl)-1-(p-bromophenyl)methane and related compounds repress survivin and decrease gamma-radiation-induced survivin in colon and pancreatic cancer cells. Int.J.Oncol. 2009;35(5):1191-1199. View abstract.
  • Staub, R. E., Feng, C., Onisko, B., Bailey, G. S., Firestone, G. L., and Bjeldanes, L. F. Fate of indole-3-carbinol in cultured human breast tumor cells. Chem.Res.Toxicol. 2002;15(2):101-109. View abstract.
  • Staub, R. E., Onisko, B., and Bjeldanes, L. F. Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells. Chem.Res.Toxicol. 2006;19(3):436-442. View abstract.
  • Stresser, D. M., Bjeldanes, L. F., Bailey, G. S., and Williams, D. E. The anticarcinogen 3,3'-diindolylmethane is an inhibitor of cytochrome P-450. J.Biochem.Toxicol. 1995;10(4):191-201. View abstract.
  • Stresser, D. M., Williams, D. E., Griffin, D. A., and Bailey, G. S. Mechanisms of tumor modulation by indole-3-carbinol. Disposition and excretion in male Fischer 344 rats. Drug Metab Dispos. 1995;23(9):965-975. View abstract.
  • Sugihara, K., Okayama, T., Kitamura, S., Yamashita, K., Yasuda, M., Miyairi, S., Minobe, Y., and Ohta, S. Comparative study of aryl hydrocarbon receptor ligand activities of six chemicals in vitro and in vivo. Arch.Toxicol. 2008;82(1):5-11. View abstract.
  • Sun, S., Han, J., Ralph, W. M., Jr., Chandrasekaran, A., Liu, K., Auborn, K. J., and Carter, T. H. Endoplasmic reticulum stress as a correlate of cytotoxicity in human tumor cells exposed to diindolylmethane in vitro. Cell Stress.Chaperones. 2004;9(1):76-87. View abstract.
  • Tadi, K., Chang, Y., Ashok, B. T., Chen, Y., Moscatello, A., Schaefer, S. D., Schantz, S. P., Policastro, A. J., Geliebter, J., and Tiwari, R. K. 3,3'-Diindolylmethane, a cruciferous vegetable derived synthetic anti-proliferative compound in thyroid disease. Biochem.Biophys.Res.Commun. 11-25-2005;337(3):1019-1025. View abstract.
  • Takahashi, N., Dashwood, R. H., Bjeldanes, L. F., Bailey, G. S., and Williams, D. E. Regulation of hepatic cytochrome P4501A by indole-3-carbinol: transient induction with continuous feeding in rainbow trout. Food Chem.Toxicol. 1995;33(2):111-120. View abstract.
  • Takahashi, N., Dashwood, R. H., Bjeldanes, L. F., Williams, D. E., and Bailey, G. S. Mechanisms of indole-3-carbinol (I3C) anticarcinogenesis: inhibition of aflatoxin B1-DNA adduction and mutagenesis by I3C acid condensation products. Food Chem.Toxicol. 1995;33(10):851-857. View abstract.
  • Takahashi, N., Stresser, D. M., Williams, D. E., and Bailey, G. S. Induction of hepatic CYP1A by indole-3-carbinol in protection against aflatoxin B1 hepatocarcinogenesis in rainbow trout. Food Chem.Toxicol. 1995;33(10):841-850. View abstract.
  • Tilton, S. C., Givan, S. A., Pereira, C. B., Bailey, G. S., and Williams, D. E. Toxicogenomic profiling of the hepatic tumor promoters indole-3-carbinol, 17beta-estradiol and beta-naphthoflavone in rainbow trout. Toxicol.Sci. 2006;90(1):61-72. View abstract.
  • Vivar, O. I., Lin, C. L., Firestone, G. L., and Bjeldanes, L. F. 3,3'-Diindolylmethane induces a G(1) arrest in human prostate cancer cells irrespective of androgen receptor and p53 status. Biochem.Pharmacol. 9-1-2009;78(5):469-476. View abstract.
  • Vivar, O. I., Saunier, E. F., Leitman, D. C., Firestone, G. L., and Bjeldanes, L. F. Selective activation of estrogen receptor-beta target genes by 3,3'-diindolylmethane. Endocrinology 2010;151(4):1662-1667. View abstract.
  • Wang, T. T., Milner, M. J., Milner, J. A., and Kim, Y. S. Estrogen receptor alpha as a target for indole-3-carbinol. J.Nutr.Biochem. 2006;17(10):659-664. View abstract.
  • Wang, Z., Yu, B. W., Rahman, K. M., Ahmad, F., and Sarkar, F. H. Induction of growth arrest and apoptosis in human breast cancer cells by 3,3-diindolylmethane is associated with induction and nuclear localization of p27kip. Mol.Cancer Ther. 2008;7(2):341-349. View abstract.
  • Wattenberg, L. W. and Loub, W. D. Inhibition of polycyclic aromatic hydrocarbon-induced neoplasia by naturally occurring indoles. Cancer Res. 1978;38(5):1410-1413. View abstract.
  • Wattenberg, L. W., Loub, W. D., Lam, L. K., and Speier, J. L. Dietary constituents altering the responses to chemical carcinogens. Fed.Proc. 5-1-1976;35(6):1327-1331. View abstract.
  • Wihlen, B., Ahmed, S., Inzunza, J., and Matthews, J. Estrogen receptor subtype- and promoter-specific modulation of aryl hydrocarbon receptor-dependent transcription. Mol.Cancer Res. 2009;7(6):977-986. View abstract.
  • Williams, D. E., Katchamar, S., Larsen-Su, S. A., Stresser, D. M., Dehal, S. S., and Kupfer, D. Concurrent flavin-containing monooxygenase down regulation and cytochrome P450 induction by dietary indoles in the rat: implication for drug-drug interactions. Adv.Exp.Med.Biol. 2001;500:635-638. View abstract.
  • Wortelboer, H. M., de Kruif, C. A., van Iersel, A. A., Falke, H. E., Noordhoek, J., and Blaauboer, B. J. Acid reaction products of indole-3-carbinol and their effects on cytochrome P450 and phase II enzymes in rat and monkey hepatocytes. Biochem.Pharmacol. 4-1-1992;43(7):1439-1447. View abstract.
  • Wortelboer, H. M., van der Linden, E. C., de Kruif, C. A., Noordhoek, J., Blaauboer, B. J., van Bladeren, P. J., and Falke, H. E. Effects of indole-3-carbinol on biotransformation enzymes in the rat: in vivo changes in liver and small intestinal mucosa in comparison with primary hepatocyte cultures. Food Chem.Toxicol. 1992;30(7):589-599. View abstract.
  • Xue, L., Firestone, G. L., and Bjeldanes, L. F. DIM stimulates IFNgamma gene expression in human breast cancer cells via the specific activation of JNK and p38 pathways. Oncogene 3-31-2005;24(14):2343-2353. View abstract.
  • Xue, L., Pestka, J. J., Li, M., Firestone, G. L., and Bjeldanes, L. F. 3,3'-Diindolylmethane stimulates murine immune function in vitro and in vivo. J.Nutr.Biochem. 2008;19(5):336-344. View abstract.
  • Yin, H., Chu, A., Li, W., Wang, B., Shelton, F., Otero, F., Nguyen, D. G., Caldwell, J. S., and Chen, Y. A. Lipid G protein-coupled receptor ligand identification using beta-arrestin PathHunter assay. J.Biol.Chem. 5-1-2009;284(18):12328-12338. View abstract.
  • Zhang, S., Shen, H. M., and Ong, C. N. Down-regulation of c-FLIP contributes to the sensitization effect of 3,3'-diindolylmethane on TRAIL-induced apoptosis in cancer cells. Mol.Cancer Ther. 2005;4(12):1972-1981. View abstract.
  • Zhang, X. and Malejka-Giganti, D. Effects of treatment of rats with indole-3-carbinol on apoptosis in the mammary gland and mammary adenocarcinomas. Anticancer Res. 2003;23(3B):2473-2479. View abstract.
  • Zhao, Y. Y., Zhou, L., Pan, Y. Z., Zhao, L. J., Liu, Y. N., Yu, H., Li, Y., and Zhao, X. J. [3,3-diindolylmethane enhances the inhibitory effect of idarubicin on the growth of human prostate cancer cells]. Zhonghua Yi.Xue.Za Zhi. 3-11-2008;88(10):661-664. View abstract.
  • Aggarwal, B. B. and Ichikawa, H. Molecular targets and anticancer potential of indole-3-carbinol and its derivatives. Cell Cycle 2005;4(9):1201-1215. View abstract.
  • Balk JL. Indole-3-carbinol for cancer prevention. Altern Med Alert 2000; 3:105-7.
  • Bonnesen C, Eggleston IM, Hayes JD. Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines. Cancer Res 2001;61:6120-30. View abstract.
  • Bradlow HL, Sepkovic DW, Telang NT, Osborne MP. Multifunctional aspects of the action of indole-3-carbinol as an antitumor agent. Ann N Y Acad Sci 1999;889:204-13. View abstract.
  • Chen I, McDougal A, Wang F, Safe S. Aryl hydrocarbon receptor-mediated antiestrogenic and antitumorigenic activity of diindolylmethane. Carcinogenesis 1998 Sep;19:1631-9. View abstract.
  • 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. Biochem Pharmacol 1996;51:1069-76. View abstract.
  • Dalessandri, K. M., Firestone, G. L., Fitch, M. D., Bradlow, H. L., and Bjeldanes, L. F. Pilot study: effect of 3,3'-diindolylmethane supplements on urinary hormone metabolites in postmenopausal women with a history of early-stage breast cancer. Nutr Cancer 2004;50(2):161-167. View abstract.
  • Firestone, G. L. and Bjeldanes, L. F. 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 2003;133(7 Suppl):2448S-2455S. View abstract.
  • Ge X, Yanni S, Rennert G, et al. 3'3-diindolylmethane induces apoptosis in human cancer cells. Biochem Biophys Res Commun 1996;228:153-8. View abstract.
  • Lake BG, Tredger JM, Renwick AB, et al. 3'3-diindolylmethane induces CYP1A2 in cultured precision-cut human liver slices. Xenobiotica 1998;28:803-11. View abstract.
  • McDougal A, Gupta MS, Ramamoorthy K, et al. Inhibition of carcinogen-induced rat mammary tumor growth and other estrogen-dependent responses by symmetrical dihalo-substituted analogs of diindolylmethane. Cancer Lett 2000;151:169-79. View abstract.
  • Natl Inst Health, Natl Inst Environmental Health Sci. Indole-3-carbinol. Available at: http://ntp-server.niehs.nih.gov.
  • Park EJ, Pezzuto JM. Botanicals in cancer chemoprevention. Cancer Metastasis Rev 2002;21:231-55. View abstract.
  • Riby JE, Chang GHF, Firestone GL, Bjeldanes LF. Ligand-independent activation of estrogen receptor function by 3,3'-diindolylmethane in human breast cancer cells. Biochem Pharmacol 2000;60:167-77. View abstract.
  • Abdelrahim, M., Newman, K., Vanderlaag, K., Samudio, I., and Safe, S. 3,3'-diindolylmethane (DIM) and its derivatives induce apoptosis in pancreatic cancer cells through endoplasmic reticulum stress-dependent upregulation of DR5. Carcinogenesis 2006;27(4):717-728. View abstract.
  • Acharya, A., Das, I., Singh, S., and Saha, T. Chemopreventive properties of indole-3-carbinol, diindolylmethane and other constituents of cardamom against carcinogenesis. Recent Pat Food Nutr.Agric. 2010;2(2):166-177. View abstract.
  • Ahmad, A., Kong, D., Sarkar, S. H., Wang, Z., Banerjee, S., and Sarkar, F. H. Inactivation of uPA and its receptor uPAR by 3,3'-diindolylmethane (DIM) leads to the inhibition of prostate cancer cell growth and migration. J.Cell Biochem. 6-1-2009;107(3):516-527. View abstract.
  • Ahmad, A., Kong, D., Wang, Z., Sarkar, S. H., Banerjee, S., and Sarkar, F. H. Down-regulation of uPA and uPAR by 3,3'-diindolylmethane contributes to the inhibition of cell growth and migration of breast cancer cells. J.Cell Biochem. 11-1-2009;108(4):916-925. View abstract.
  • Ahmad, A., Sakr, W. A., and Rahman, K. M. Anticancer properties of indole compounds: mechanism of apoptosis induction and role in chemotherapy. Curr.Drug Targets. 2010;11(6):652-666. View abstract.
  • Albert-Puleo, M. Physiological effects of cabbage with reference to its potential as a dietary cancer-inhibitor and its use in ancient medicine. J.Ethnopharmacol. 1983;9(2-3):261-272. View abstract.
  • Ali, S., Banerjee, S., Ahmad, A., El-Rayes, B. F., Philip, P. A., and Sarkar, F. H. Apoptosis-inducing effect of erlotinib is potentiated by 3,3'-diindolylmethane in vitro and in vivo using an orthotopic model of pancreatic cancer. Mol.Cancer Ther. 2008;7(6):1708-1719. View abstract.
  • Ali, S., Banerjee, S., Schaffert, J. M., El-Rayes, B. F., Philip, P. A., and Sarkar, F. H. Concurrent inhibition of NF-kappaB, cyclooxygenase-2, and epidermal growth factor receptor leads to greater anti-tumor activity in pancreatic cancer. J.Cell Biochem. 2010;110(1):171-181. View abstract.
  • Ali, S., Varghese, L., Pereira, L., Tulunay-Ugur, O. E., Kucuk, O., Carey, T. E., Wolf, G. T., and Sarkar, F. H. Sensitization of squamous cell carcinoma to cisplatin induced killing by natural agents. Cancer Lett. 6-18-2009;278(2):201-209. View abstract.
  • Anderton, M. J., Jukes, R., Lamb, J. H., Manson, M. M., Gescher, A., Steward, W. P., and Williams, M. L. Liquid chromatographic assay for the simultaneous determination of indole-3-carbinol and its acid condensation products in plasma. J.Chromatogr.B Analyt.Technol.Biomed.Life Sci. 4-25-2003;787(2):281-291. View abstract.
  • Anderton, M. J., Manson, M. M., Verschoyle, R. D., Gescher, A., Lamb, J. H., Farmer, P. B., Steward, W. P., and Williams, M. L. Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice. Clin.Cancer Res. 8-1-2004;10(15):5233-5241. View abstract.
  • Anderton, M. J., Manson, M. M., Verschoyle, R., Gescher, A., Steward, W. P., Williams, M. L., and Mager, D. E. Physiological modeling of formulated and crystalline 3,3'-diindolylmethane pharmacokinetics following oral administration in mice. Drug Metab Dispos. 2004;32(6):632-638. View abstract.
  • Arnao, M. B., Sanchez-Bravo, J., and Acosta, M. Indole-3-carbinol as a scavenger of free radicals. Biochem.Mol.Biol.Int. 1996;39(6):1125-1134. View abstract.
  • Auborn, K. J., Fan, S., Rosen, E. M., Goodwin, L., Chandraskaren, A., Williams, D. E., Chen, D., and Carter, T. H. Indole-3-carbinol is a negative regulator of estrogen. J.Nutr. 2003;133(7 Suppl):2470S-2475S. View abstract.
  • Azmi, A. S., Ahmad, A., Banerjee, S., Rangnekar, V. M., Mohammad, R. M., and Sarkar, F. H. Chemoprevention of pancreatic cancer: characterization of Par-4 and its modulation by 3,3' diindolylmethane (DIM). Pharm.Res. 2008;25(9):2117-2124. View abstract.
  • Benabadji, S. H., Wen, R., Zheng, J. B., Dong, X. C., and Yuan, S. G. Anticarcinogenic and antioxidant activity of diindolylmethane derivatives. Acta Pharmacol.Sin. 2004;25(5):666-671. View abstract.
  • Bhatnagar, N., Li, X., Chen, Y., Zhou, X., Garrett, S. H., and Guo, B. 3,3'-diindolylmethane enhances the efficacy of butyrate in colon cancer prevention through down-regulation of survivin. Cancer Prev.Res.(Phila) 2009;2(6):581-589. View abstract.
  • Bhuiyan, M. M., Li, Y., Banerjee, S., Ahmed, F., Wang, Z., Ali, S., and Sarkar, F. H. Down-regulation of androgen receptor by 3,3'-diindolylmethane contributes to inhibition of cell proliferation and induction of apoptosis in both hormone-sensitive LNCaP and insensitive C4-2B prostate cancer cells. Cancer Res. 10-15-2006;66(20):10064-10072. View abstract.
  • Bovee, T. F., Schoonen, W. G., Hamers, A. R., Bento, M. J., and Peijnenburg, A. A. Screening of synthetic and plant-derived compounds for (anti)estrogenic and (anti)androgenic activities. Anal.Bioanal.Chem. 2008;390(4):1111-1119. View abstract.
  • Bradfield, C. A. and Bjeldanes, L. F. Structure-activity relationships of dietary indoles: a proposed mechanism of action as modifiers of xenobiotic metabolism. J.Toxicol.Environ.Health 1987;21(3):311-323. View abstract.
  • Bradlow, H. L. and Zeligs, M. A. Diindolylmethane (DIM) spontaneously forms from indole-3-carbinol (I3C) during cell culture experiments. In Vivo 2010;24(4):387-391. View abstract.
  • Carter, T. H., Liu, K., Ralph, W., Jr., Chen, D., Qi, M., Fan, S., Yuan, F., Rosen, E. M., and Auborn, K. J. Diindolylmethane alters gene expression in human keratinocytes in vitro. J.Nutr. 2002;132(11):3314-3324. View abstract.
  • Chang, X., Firestone, G. L., and Bjeldanes, L. F. Inhibition of growth factor-induced Ras signaling in vascular endothelial cells and angiogenesis by 3,3'-diindolylmethane. Carcinogenesis 2006;27(3):541-550. View abstract.
  • Chang, X., Tou, J. C., Hong, C., Kim, H. A., Riby, J. E., Firestone, G. L., and Bjeldanes, L. F. 3,3'-Diindolylmethane inhibits angiogenesis and the growth of transplantable human breast carcinoma in athymic mice. Carcinogenesis 2005;26(4):771-778. View abstract.
  • Chang, Y. C., Riby, J., Chang, G. H., Peng, B. C., Firestone, G., and Bjeldanes, L. F. Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3'-diindolylmethane, a major in vivo product of dietary indole-3-carbinol. Biochem.Pharmacol. 9-1-1999;58(5):825-834. View abstract.
  • Chen, D. Z., Qi, M., Auborn, K. J., and Carter, T. H. Indole-3-carbinol and diindolylmethane induce apoptosis of human cervical cancer cells and in murine HPV16-transgenic preneoplastic cervical epithelium. J.Nutr. 2001;131(12):3294-3302. View abstract.
  • Chen, I., Hsieh, T., Thomas, T., and Safe, S. Identification of estrogen-induced genes downregulated by AhR agonists in MCF-7 breast cancer cells using suppression subtractive hybridization. Gene 1-10-2001;262(1-2):207-214. View abstract.
  • Chen, Y., Xu, J., Jhala, N., Pawar, P., Zhu, Z. B., Ma, L., Byon, C. H., and McDonald, J. M. Fas-mediated apoptosis in cholangiocarcinoma cells is enhanced by 3,3'-diindolylmethane through inhibition of AKT signaling and FLICE-like inhibitory protein. Am.J.Pathol. 2006;169(5):1833-1842. View abstract.
  • Chinnakannu, K., Chen, D., Li, Y., Wang, Z., Dou, Q. P., Reddy, G. P., and Sarkar, F. H. Cell cycle-dependent effects of 3,3'-diindolylmethane on proliferation and apoptosis of prostate cancer cells. J.Cell Physiol 2009;219(1):94-99. View abstract.
  • Chintharlapalli, S., Papineni, S., and Safe, S. 1,1-bis(3'-indolyl)-1-(p-substitutedphenyl)methanes inhibit growth, induce apoptosis, and decrease the androgen receptor in LNCaP prostate cancer cells through peroxisome proliferator-activated receptor gamma-independent pathways. Mol.Pharmacol. 2007;71(2):558-569. View abstract.
  • Chintharlapalli, S., Smith, R., III, Samudio, I., Zhang, W., and Safe, S. 1,1-Bis(3'-indolyl)-1-(p-substitutedphenyl)methanes induce peroxisome proliferator-activated receptor gamma-mediated growth inhibition, transactivation, and differentiation markers in colon cancer cells. Cancer Res. 9-1-2004;64(17):5994-6001. View abstract.
  • Cho, H. J., Seon, M. R., Lee, Y. M., Kim, J., Kim, J. K., Kim, S. G., and Park, J. H. 3,3'-Diindolylmethane suppresses the inflammatory response to lipopolysaccharide in murine macrophages. J.Nutr. 2008;138(1):17-23. View abstract.
  • Cho, S. D., Lee, S. O., Chintharlapalli, S., Abdelrahim, M., Khan, S., Yoon, K., Kamat, A. M., and Safe, S. Activation of nerve growth factor-induced B alpha by methylene-substituted diindolylmethanes in bladder cancer cells induces apoptosis and inhibits tumor growth. Mol.Pharmacol. 2010;77(3):396-404. View abstract.
  • Cho, S. D., Lei, P., Abdelrahim, M., Yoon, K., Liu, S., Guo, J., Papineni, S., Chintharlapalli, S., and Safe, S. 1,1-bis(3'-indolyl)-1-(p-methoxyphenyl)methane activates Nur77-independent proapoptotic responses in colon cancer cells. Mol.Carcinog. 2008;47(4):252-263. View abstract.
  • Choi, K. H., Kim, H. K., Kim, J. H., Choi, E. S., Shin, J. A., Lee, S. O., Chintharlapalli, S., Safe, S., Abdelrahim, M., Kong, G., Choi, H. S., Jung, J. Y., Cho, H. T., Cho, N. P., and Cho, S. D. The p38 MAPK pathway is critical for 5,5'-dibromodiindolylmethane-induced apoptosis to prevent oral squamous carcinoma cells. Eur.J.Cancer Prev. 2010;19(2):153-159. View abstract.
  • Contractor, R., Samudio, I. J., Estrov, Z., Harris, D., McCubrey, J. A., Safe, S. H., Andreeff, M., and Konopleva, M. A novel ring-substituted diindolylmethane,1,1-bis[3'-(5-methoxyindolyl)]-1-(p-t-butylphenyl) methane, inhibits extracellular signal-regulated kinase activation and induces apoptosis in acute myelogenous leukemia. Cancer Res. 4-1-2005;65(7):2890-2898. View abstract.
  • Crowell, J. A., Page, J. G., Levine, B. S., Tomlinson, M. J., and Hebert, C. D. Indole-3-carbinol, but not its major digestive product 3,3'-diindolylmethane, induces reversible hepatocyte hypertrophy and cytochromes P450. Toxicol.Appl.Pharmacol. 3-1-2006;211(2):115-123. View abstract.
  • Dashwood, R. H., Fong, A. T., Arbogast, D. N., Bjeldanes, L. F., Hendricks, J. D., and Bailey, G. S. Anticarcinogenic activity of indole-3-carbinol acid products: ultrasensitive bioassay by trout embryo microinjection. Cancer Res. 7-1-1994;54(13):3617-3619. View abstract.
  • Dashwood, R. H., Uyetake, L., Fong, A. T., Hendricks, J. D., and Bailey, G. S. In vivo disposition of the natural anti-carcinogen indole-3-carbinol after po administration to rainbow trout. Food Chem.Toxicol. 1989;27(6):385-392. View abstract.
  • de Kruif, C. A., Marsman, J. W., Venekamp, J. C., Falke, H. E., Noordhoek, J., Blaauboer, B. J., and Wortelboer, H. M. Structure elucidation of acid reaction products of indole-3-carbinol: detection in vivo and enzyme induction in vitro. Chem.Biol.Interact. 1991;80(3):303-315. View abstract.
  • Degner, S. C., Papoutsis, A. J., Selmin, O., and Romagnolo, D. F. Targeting of aryl hydrocarbon receptor-mediated activation of cyclooxygenase-2 expression by the indole-3-carbinol metabolite 3,3'-diindolylmethane in breast cancer cells. J.Nutr. 2009;139(1):26-32. View abstract.
  • Del Priore G., Gudipudi, D. K., Montemarano, N., Restivo, A. M., Malanowska-Stega, J., and Arslan, A. A. Oral diindolylmethane (DIM): pilot evaluation of a nonsurgical treatment for cervical dysplasia. Gynecol.Oncol. 2010;116(3):464-467. View abstract.
  • Dong, L., Xia, S., Gao, F., Zhang, D., Chen, J., and Zhang, J. 3,3'-Diindolylmethane attenuates experimental arthritis and osteoclastogenesis. Biochem.Pharmacol. 3-1-2010;79(5):715-721. View abstract.
  • Elackattu, A. P., Feng, L., and Wang, Z. A controlled safety study of diindolylmethane in the immature rat model. Laryngoscope 2009;119(9):1803-1808. View abstract.
  • Fan, S., Meng, Q., Saha, T., Sarkar, F. H., and Rosen, E. M. Low concentrations of diindolylmethane, a metabolite of indole-3-carbinol, protect against oxidative stress in a BRCA1-dependent manner. Cancer Res. 8-1-2009;69(15):6083-6091. View abstract.
  • Fares, F., Azzam, N., Appel, B., Fares, B., and Stein, A. The potential efficacy of 3,3'-diindolylmethane in prevention of prostate cancer development. Eur.J.Cancer Prev. 2010;19(3):199-203. View abstract.
  • Firestone, G. L. and Sundar, S. N. Minireview: modulation of hormone receptor signaling by dietary anticancer indoles. Mol.Endocrinol. 2009;23(12):1940-1947. View abstract.
  • Gallagher, E. P. Using salmonid microarrays to understand the dietary modulation of carcinogenesis in rainbow trout. Toxicol.Sci. 2006;90(1):1-4. View abstract.
  • Gamet-Payrastre, L., Lumeau, S., Gasc, N., Cassar, G., Rollin, P., and Tulliez, J. Selective cytostatic and cytotoxic effects of glucosinolates hydrolysis products on human colon cancer cells in vitro. Anticancer Drugs 1998;9(2):141-148. View abstract.
  • Garikapaty, V. P., Ashok, B. T., Tadi, K., Mittelman, A., and Tiwari, R. K. 3,3'-Diindolylmethane downregulates pro-survival pathway in hormone independent prostate cancer. Biochem.Biophys.Res.Commun. 2-10-2006;340(2):718-725. View abstract.
  • Garikapaty, V. P., Ashok, B. T., Tadi, K., Mittelman, A., and Tiwari, R. K. Synthetic dimer of indole-3-carbinol: second generation diet derived anti-cancer agent in hormone sensitive prostate cancer. Prostate 4-1-2006;66(5):453-462. View abstract.
  • Ge, X., Fares, F. A., and Yannai, S. Induction of apoptosis in MCF-7 cells by indole-3-carbinol is independent of p53 and bax. Anticancer Res. 1999;19(4B):3199-3203. View abstract.
  • Gong, Y., Firestone, G. L., and Bjeldanes, L. F. 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. 2006;69(4):1320-1327. View abstract.
  • Gong, Y., Sohn, H., Xue, L., Firestone, G. L., and Bjeldanes, L. F. 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. 5-1-2006;66(9):4880-4887. View abstract.
  • Gross-Steinmeyer, K., Stapleton, P. L., Liu, F., Tracy, J. H., Bammler, T. K., Quigley, S. D., Farin, F. M., Buhler, D. R., Safe, S. H., Strom, S. C., and Eaton, D. L. Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes. Xenobiotica 2004;34(7):619-632. View abstract.
  • Gross-Steinmeyer, K., Stapleton, P. L., Tracy, J. H., Bammler, T. K., Strom, S. C., Buhler, D. R., and Eaton, D. L. Modulation of aflatoxin B1-mediated genotoxicity in primary cultures of human hepatocytes by diindolylmethane, curcumin, and xanthohumols. Toxicol Sci. 2009;112(2):303-310. View abstract.
  • Gullett, N. P., Ruhul Amin, A. R., Bayraktar, S., Pezzuto, J. M., Shin, D. M., Khuri, F. R., Aggarwal, B. B., Surh, Y. J., and Kucuk, O. Cancer prevention with natural compounds. Semin.Oncol. 2010;37(3):258-281. View abstract.
  • Heath, E. I., Heilbrun, L. K., Li, J., Vaishampayan, U., Harper, F., Pemberton, P., and Sarkar, F. H. A phase I dose-escalation study of oral BR-DIM (BioResponse 3,3'- Diindolylmethane) in castrate-resistant, non-metastatic prostate cancer. Am.J.Transl.Res. 2010;2(4):402-411. View abstract.
  • Hestermann, E. V. and Brown, M. Agonist and chemopreventative ligands induce differential transcriptional cofactor recruitment by aryl hydrocarbon receptor. Mol.Cell Biol. 2003;23(21):7920-7925. View abstract.
  • Hong, C., Firestone, G. L., and Bjeldanes, L. F. Bcl-2 family-mediated apoptotic effects of 3,3'-diindolylmethane (DIM) in human breast cancer cells. Biochem.Pharmacol. 3-15-2002;63(6):1085-1097. View abstract.
  • Hong, C., Kim, H. A., Firestone, G. L., and Bjeldanes, L. F. 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 2002;23(8):1297-1305. View abstract.
  • Hong, J., Samudio, I., Liu, S., Abdelrahim, M., and Safe, S. Peroxisome proliferator-activated receptor gamma-dependent activation of p21 in Panc-28 pancreatic cancer cells involves Sp1 and Sp4 proteins. Endocrinology 2004;145(12):5774-5785. View abstract.
  • Hsu, E. L., Chen, N., Westbrook, A., Wang, F., Zhang, R., Taylor, R. T., and Hankinson, O. CXCR4 and CXCL12 down-regulation: a novel mechanism for the chemoprotection of 3,3'-diindolylmethane for breast and ovarian cancers. Cancer Lett. 6-28-2008;265(1):113-123. View abstract.
  • Hsu, E. L., Chen, N., Westbrook, A., Wang, F., Zhang, R., Taylor, R. T., and Hankinson, O. Modulation of CXCR4, CXCL12, and Tumor Cell Invasion Potential In Vitro by Phytochemicals. J.Oncol. 2009;2009:491985. View abstract.
  • Hsu, J. C., Zhang, J., Dev, A., Wing, A., Bjeldanes, L. F., and Firestone, G. L. Indole-3-carbinol inhibition of androgen receptor expression and downregulation of androgen responsiveness in human prostate cancer cells. Carcinogenesis 2005;26(11):1896-1904. View abstract.
  • Huang, J., Plass, C., and Gerhauser, C. Cancer chemoprevention by targeting the epigenome. Curr Drug Targets. 2011;12(13):1925-1956. View abstract.
  • Huang, Z., Zuo, L., Zhang, Z., Liu, J., Chen, J., Dong, L., and Zhang, J. 3,3'-Diindolylmethane decreases VCAM-1 expression and alleviates experimental colitis via a BRCA1-dependent antioxidant pathway. Free Radic.Biol.Med. 1-15-2011;50(2):228-236. View abstract.
  • Ichite, N., Chougule, M. B., Jackson, T., Fulzele, S. V., Safe, S., and Singh, M. Enhancement of docetaxel anticancer activity by a novel diindolylmethane compound in human non-small cell lung cancer. Clin.Cancer Res. 1-15-2009;15(2):543-552. View abstract.
  • Ichite, N., Chougule, M., Patel, A. R., Jackson, T., Safe, S., and Singh, M. Inhalation delivery of a novel diindolylmethane derivative for the treatment of lung cancer. Mol.Cancer Ther. 2010;9(11):3003-3014. View abstract.
  • Jellinck, P. H., Forkert, P. G., Riddick, D. S., Okey, A. B., Michnovicz, J. J., and Bradlow, H. L. Ah receptor binding properties of indole carbinols and induction of hepatic estradiol hydroxylation. Biochem.Pharmacol. 3-9-1993;45(5):1129-1136. View abstract.
  • Jellinck, P. H., Makin, H. L., Sepkovic, D. W., and Bradlow, H. L. Influence of indole carbinols and growth hormone on the metabolism of 4-androstenedione by rat liver microsomes. J.Steroid Biochem.Mol.Biol. 1993;46(6):791-798. View abstract.
  • Jin, Y., Zou, X., and Feng, X. 3,3'-Diindolylmethane negatively regulates Cdc25A and induces a G2/M arrest by modulation of microRNA 21 in human breast cancer cells. Anticancer Drugs 2010;21(9):814-822. View abstract.
  • Kandala, P. K. and Srivastava, S. K. Activation of checkpoint kinase 2 by 3,3'-diindolylmethane is required for causing G2/M cell cycle arrest in human ovarian cancer cells. Mol.Pharmacol. 2010;78(2):297-309. View abstract.
  • Kassie, F., Anderson, L. B., Scherber, R., Yu, N., Lahti, D., Upadhyaya, P., and Hecht, S. S. Indole-3-carbinol inhibits 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone plus benzo(a)pyrene-induced lung tumorigenesis in A/J mice and modulates carcinogen-induced alterations in protein levels. Cancer Res. 7-1-2007;67(13):6502-6511. View abstract.
  • Kassie, F., Melkamu, T., Endalew, A., Upadhyaya, P., Luo, X., and Hecht, S. S. Inhibition of lung carcinogenesis and critical cancer-related signaling pathways by N-acetyl-S-(N-2-phenethylthiocarbamoyl)-l-cysteine, indole-3-carbinol and myo-inositol, alone and in combination. Carcinogenesis 2010;31(9):1634-1641. View abstract.
  • Katchamart, S., Stresser, D. M., Dehal, S. S., Kupfer, D., and Williams, D. E. Concurrent flavin-containing monooxygenase down-regulation and cytochrome P-450 induction by dietary indoles in rat: implications for drug-drug interaction. Drug Metab Dispos. 2000;28(8):930-936. View abstract.
  • Khwaja, F. S., Wynne, S., Posey, I., and Djakiew, D. 3,3'-diindolylmethane induction of p75NTR-dependent cell death via the p38 mitogen-activated protein kinase pathway in prostate cancer cells. Cancer Prev.Res.(Phila) 2009;2(6):566-571. View abstract.
  • Kim, E. J., Park, H., Kim, J., and Park, J. H. 3,3'-diindolylmethane suppresses 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and tumor promotion in mouse skin via the downregulation of inflammatory mediators. Mol.Carcinog. 2010;49(7):672-683. View abstract.
  • Kim, E. J., Park, S. Y., Shin, H. K., Kwon, D. Y., Surh, Y. J., and Park, J. H. Activation of caspase-8 contributes to 3,3'-Diindolylmethane-induced apoptosis in colon cancer cells. J.Nutr. 2007;137(1):31-36. View abstract.
  • Kim, E. J., Shin, M., Park, H., Hong, J. E., Shin, H. K., Kim, J., Kwon, D. Y., and Park, J. H. Oral administration of 3,3'-diindolylmethane inhibits lung metastasis of 4T1 murine mammary carcinoma cells in BALB/c mice. J.Nutr. 2009;139(12):2373-2379. View abstract.
  • Kim, Y. H., Kwon, H. S., Kim, D. H., Shin, E. K., Kang, Y. H., Park, J. H., Shin, H. K., and Kim, J. K. 3,3'-diindolylmethane attenuates colonic inflammation and tumorigenesis in mice. Inflamm.Bowel.Dis. 2009;15(8):1164-1173. View abstract.
  • Kim, Y. S. and Milner, J. A. Targets for indole-3-carbinol in cancer prevention. J.Nutr.Biochem. 2005;16(2):65-73. View abstract.
  • Kong, D., Banerjee, S., Huang, W., Li, Y., Wang, Z., Kim, H. R., and Sarkar, F. H. Mammalian target of rapamycin repression by 3,3'-diindolylmethane inhibits invasion and angiogenesis in platelet-derived growth factor-D-overexpressing PC3 cells. Cancer Res. 3-15-2008;68(6):1927-1934. View abstract.
  • Kong, D., Li, Y., Wang, Z., Banerjee, S., and Sarkar, F. H. Inhibition of angiogenesis and invasion by 3,3'-diindolylmethane is mediated by the nuclear factor-kappaB downstream target genes MMP-9 and uPA that regulated bioavailability of vascular endothelial growth factor in prostate cancer. Cancer Res. 4-1-2007;67(7):3310-3319. View abstract.
  • Kunimasa, K., Kobayashi, T., Kaji, K., and Ohta, T. Antiangiogenic effects of indole-3-carbinol and 3,3'-diindolylmethane are associated with their differential regulation of ERK1/2 and Akt in tube-forming HUVEC. J.Nutr. 2010;140(1):1-6. View abstract.
  • Le, H. T., Schaldach, C. M., Firestone, G. L., and Bjeldanes, L. F. Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells. J.Biol.Chem. 6-6-2003;278(23):21136-21145. View abstract.
  • Lee, S. H., Kim, J. S., Yamaguchi, K., Eling, T. E., and Baek, S. J. Indole-3-carbinol and 3,3'-diindolylmethane induce expression of NAG-1 in a p53-independent manner. Biochem.Biophys.Res.Commun. 3-4-2005;328(1):63-69. View abstract.
  • Lee, S. O., Li, X., Khan, S., and Safe, S. Targeting NR4A1 (TR3) in cancer cells and tumors. Expert.Opin.Ther.Targets. 2011;15(2):195-206. View abstract.
  • Leibelt, D. A., Hedstrom, O. R., Fischer, K. A., Pereira, C. B., and Williams, D. E. Evaluation of chronic dietary exposure to indole-3-carbinol and absorption-enhanced 3,3'-diindolylmethane in sprague-dawley rats. Toxicol.Sci. 2003;74(1):10-21. View abstract.
  • Leong, H., Firestone, G. L., and Bjeldanes, L. F. 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 2001;22(11):1809-1817. View abstract.
  • Leong, H., Riby, J. E., Firestone, G. L., and Bjeldanes, L. F. 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. 2004;18(2):291-302. View abstract.
  • Li, Y., Kong, D., Wang, Z., and Sarkar, F. H. Regulation of microRNAs by natural agents: an emerging field in chemoprevention and chemotherapy research. Pharm.Res. 2010;27(6):1027-1041. View abstract.
  • Li, Y., Li, X., and Guo, B. Chemopreventive agent 3,3'-diindolylmethane selectively induces proteasomal degradation of class I histone deacetylases. Cancer Res. 1-15-2010;70(2):646-654. View abstract.
  • Li, Y., Li, X., and Sarkar, F. H. Gene expression profiles of I3C- and DIM-treated PC3 human prostate cancer cells determined by cDNA microarray analysis. J.Nutr. 2003;133(4):1011-1019. View abstract.
  • Li, Y., VandenBoom, T. G., Kong, D., Wang, Z., Ali, S., Philip, P. A., and Sarkar, F. H. Up-regulation of miR-200 and let-7 by natural agents leads to the reversal of epithelial-to-mesenchymal transition in gemcitabine-resistant pancreatic cancer cells. Cancer Res. 8-15-2009;69(16):6704-6712. View abstract.
  • Li, Y., VandenBoom, T. G., Wang, Z., Kong, D., Ali, S., Philip, P. A., and Sarkar, F. H. miR-146a suppresses invasion of pancreatic cancer cells. Cancer Res. 2-15-2010;70(4):1486-1495. View abstract.
  • Li, Y., Wang, Z., Kong, D., Murthy, S., Dou, Q. P., Sheng, S., Reddy, G. P., and Sarkar, F. H. Regulation of FOXO3a/beta-catenin/GSK-3beta signaling by 3,3'-diindolylmethane contributes to inhibition of cell proliferation and induction of apoptosis in prostate cancer cells. J.Biol.Chem. 7-20-2007;282(29):21542-21550. View abstract.
  • Liu, S., Abdelrahim, M., Khan, S., Ariazi, E., Jordan, V. C., and Safe, S. Aryl hydrocarbon receptor agonists directly activate estrogen receptor alpha in MCF-7 breast cancer cells. Biol.Chem. 2006;387(9):1209-1213. View abstract.
  • Loub, W. D., Wattenberg, L. W., and Davis, D. W. Aryl hydrocarbon hydroxylase induction in rat tissues by naturally occurring indoles of cruciferous plants. J.Natl.Cancer Inst. 1975;54(4):985-988. View abstract.
  • Maciejewska, D., Rasztawicka, M., Wolska, I., Anuszewska, E., and Gruber, B. Novel 3,3'-diindolylmethane derivatives: synthesis and cytotoxicity, structural characterization in solid state. Eur.J.Med.Chem. 2009;44(10):4136-4147. View abstract.
  • McCarty, M. F. and Block, K. I. Multifocal angiostatic therapy: an update. Integr.Cancer Ther. 2005;4(4):301-314. View abstract.
  • McDanell, R., McLean, A. E., Hanley, A. B., Heaney, R. K., and Fenwick, G. R. Differential induction of mixed-function oxidase (MFO) activity in rat liver and intestine by diets containing processed cabbage: correlation with cabbage levels of glucosinolates and glucosinolate hydrolysis products. Food Chem.Toxicol. 1987;25(5):363-368. View abstract.
  • McDougal, A., Gupta, M. S., Morrow, D., Ramamoorthy, K., Lee, J. E., and Safe, S. H. Methyl-substituted diindolylmethanes as inhibitors of estrogen-induced growth of T47D cells and mammary tumors in rats. Breast Cancer Res.Treat. 2001;66(2):147-157. View abstract.
  • McGuire, K. P., Ngoubilly, N., Neavyn, M., and Lanza-Jacoby, S. 3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells. J.Surg.Res. 5-15-2006;132(2):208-213. View abstract.
  • Moiseeva, E. P., Almeida, G. M., Jones, G. D., and Manson, M. M. Extended treatment with physiologic concentrations of dietary phytochemicals results in altered gene expression, reduced growth, and apoptosis of cancer cells. Mol.Cancer Ther. 2007;6(11):3071-3079. View abstract.
  • Nachshon-Kedmi, M., Fares, F. A., and Yannai, S. Therapeutic activity of 3,3'-diindolylmethane on prostate cancer in an in vivo model. Prostate 10-1-2004;61(2):153-160. View abstract.
  • Nachshon-Kedmi, M., Yannai, S., and Fares, F. A. Induction of apoptosis in human prostate cancer cell line, PC3, by 3,3'-diindolylmethane through the mitochondrial pathway. Br.J.Cancer 10-4-2004;91(7):1358-1363. View abstract.
  • Nachshon-Kedmi, M., Yannai, S., Haj, A., and Fares, F. A. Indole-3-carbinol and 3,3'-diindolylmethane induce apoptosis in human prostate cancer cells. Food Chem.Toxicol. 2003;41(6):745-752. View abstract.
  • Nguyen, H. H., Aronchik, I., Brar, G. A., Nguyen, D. H., Bjeldanes, L. F., and Firestone, G. L. The dietary phytochemical indole-3-carbinol is a natural elastase enzymatic inhibitor that disrupts cyclin E protein processing. Proc.Natl.Acad.Sci.U.S.A 12-16-2008;105(50):19750-19755. View abstract.
  • Noguchi-Yachide, T., Tetsuhashi, M., Aoyama, H., and Hashimoto, Y. Enhancement of chemically-induced HL-60 cell differentiation by 3,3'-diindolylmethane derivatives. Chem.Pharm.Bull.(Tokyo) 2009;57(5):536-540. View abstract.
  • Okino, S. T., Pookot, D., Basak, S., and Dahiya, R. Toxic and chemopreventive ligands preferentially activate distinct aryl hydrocarbon receptor pathways: implications for cancer prevention. Cancer Prev.Res.(Phila) 2009;2(3):251-256. View abstract.
  • Pappa, G., Lichtenberg, M., Iori, R., Barillari, J., Bartsch, H., and Gerhauser, C. Comparison of growth inhibition profiles and mechanisms of apoptosis induction in human colon cancer cell lines by isothiocyanates and indoles from Brassicaceae. Mutat.Res. 7-25-2006;599(1-2):76-87. View abstract.
  • Pappa, G., Strathmann, J., Lowinger, M., Bartsch, H., and Gerhauser, C. Quantitative combination effects between sulforaphane and 3,3'-diindolylmethane on proliferation of human colon cancer cells in vitro. Carcinogenesis 2007;28(7):1471-1477. View abstract.
  • Parkin, D. R. and Malejka-Giganti, D. Differences in the hepatic P450-dependent metabolism of estrogen and tamoxifen in response to treatment of rats with 3,3'-diindolylmethane and its parent compound indole-3-carbinol. Cancer Detect.Prev. 2004;28(1):72-79. View abstract.
  • Parkin, D. R., Lu, Y., Bliss, R. L., and Malejka-Giganti, D. Inhibitory effects of a dietary phytochemical 3,3'-diindolylmethane on the phenobarbital-induced hepatic CYP mRNA expression and CYP-catalyzed reactions in female rats. Food Chem.Toxicol. 2008;46(7):2451-2458. View abstract.
  • Qin, C., Morrow, D., Stewart, J., Spencer, K., Porter, W., Smith, R., III, Phillips, T., Abdelrahim, M., Samudio, I., and Safe, S. A new class of peroxisome proliferator-activated receptor gamma (PPARgamma) agonists that inhibit growth of breast cancer cells: 1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methanes. Mol.Cancer Ther. 2004;3(3):247-260. View abstract.
  • Rahimi, M., Huang, K. L., and Tang, C. K. 3,3'-Diindolylmethane (DIM) inhibits the growth and invasion of drug-resistant human cancer cells expressing EGFR mutants. Cancer Lett. 9-1-2010;295(1):59-68. View abstract.
  • Rahman, K. M., Banerjee, S., Ali, S., Ahmad, A., Wang, Z., Kong, D., and Sakr, W. A. 3,3'-Diindolylmethane enhances taxotere-induced apoptosis in hormone-refractory prostate cancer cells through survivin down-regulation. Cancer Res. 5-15-2009;69(10):4468-4475. View abstract.
  • Rahman, K. W. and Sarkar, F. H. Inhibition of nuclear translocation of nuclear factor-(kappa)B contributes to 3,3'-diindolylmethane-induced apoptosis in breast cancer cells. Cancer Res. 1-1-2005;65(1):364-371. View abstract.
  • Rahman, K. W., Li, Y., Wang, Z., Sarkar, S. H., and Sarkar, F. H. Gene expression profiling revealed survivin as a target of 3,3'-diindolylmethane-induced cell growth inhibition and apoptosis in breast cancer cells. Cancer Res. 5-1-2006;66(9):4952-4960. View abstract.
  • Rajoria, S., Suriano, R., Wilson, Y. L., Schantz, S. P., Moscatello, A., Geliebter, J., and Tiwari, R. K. 3,3'-diindolylmethane inhibits migration and invasion of human cancer cells through combined suppression of ERK and AKT pathways. Oncol.Rep. 2011;25(2):491-497. View abstract.
  • Reed, G. A., Arneson, D. W., Putnam, W. C., Smith, H. J., Gray, J. C., Sullivan, D. K., Mayo, M. S., Crowell, J. A., and Hurwitz, A. Single-dose and multiple-dose administration of indole-3-carbinol to women: pharmacokinetics based on 3,3'-diindolylmethane. Cancer Epidemiol.Biomarkers Prev. 2006;15(12):2477-2481. View abstract.


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