1968-05-4 | 3,3'-Diindolylmethane

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$7.00	$5.00
10g	98%	in stock	$13.00	$9.00
25g	98%	in stock	$19.00	$14.00
100g	98%	in stock	$42.00	$30.00
500g	98%	in stock	$194.00	$136.00

Description

• Catalog Number: AB54406
• Chemical Name: 3,3'-Diindolylmethane
• CAS Number: 1968-05-4
• Molecular Formula: C17H14N2
• Molecular Weight: 246.3065
• MDL Number: MFCD00195766
• SMILES: c1ccc2c(c1)c(c[nH]2)Cc1c[nH]c2c1cccc2
• NSC Number: 708486

Computed Properties

• Complexity: 286
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 19
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 2
• XLogP3: 4.3

Literature

• Inhibitory effects of 3,3'-diindolylmethane on epithelial-mesenchymal transition induced by endocrine disrupting chemicals in cellular and xenograft mouse models of breast cancer.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20171101

• Endocrine Disruption throughout the Hypothalamus-Pituitary-Gonadal-Liver (HPGL) Axis in Marine Medaka (Oryzias melastigma) Chronically Exposed to the Antifouling and Chemopreventive Agent, 3,3'-Diindolylmethane (DIM).

  Chemical research in toxicology 20160620

• The estrogenic effect of trigonelline and 3,3-diindolymethane on cell growth in non-malignant colonocytes.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20160101

• A therapeutically relevant, 3,3'-diindolylmethane derivative NGD16 attenuates angiogenesis by targeting glucose regulated protein, 78kDa (GRP78).

  Chemico-biological interactions 20150505

• Diindolylmethane, a naturally occurring compound, induces CYP3A4 and MDR1 gene expression by activating human PXR.

  Toxicology letters 20150203

• Sulindac, 3,3'-diindolylmethane and curcumin reduce carcinogenesis in the Pirc rat, an Apc-driven model of colon carcinogenesis.

  BMC cancer 20150101

• 3,3'-Diindolylmethane inhibits lipopolysaccharide-induced microglial hyperactivation and attenuates brain inflammation.

  Toxicological sciences : an official journal of the Society of Toxicology 20140101

• Natural indoles, indole-3-carbinol and 3,3'-diindolymethane, inhibit T cell activation by staphylococcal enterotoxin B through epigenetic regulation involving HDAC expression.

  Toxicology and applied pharmacology 20140101

• Effects of sulforaphane and 3,3'-diindolylmethane on genome-wide promoter methylation in normal prostate epithelial cells and prostate cancer cells.

  PloS one 20140101

• Pleiotropic effects of the sirtuin inhibitor sirtinol involves concentration-dependent modulation of multiple nuclear receptor-mediated pathways in androgen-responsive prostate cancer cell LNCaP.

  Molecular carcinogenesis 20130901

• The aryl hydrocarbon receptor and estrogen receptor alpha differentially modulate nuclear factor erythroid-2-related factor 2 transactivation in MCF-7 breast cancer cells.

  Toxicology and applied pharmacology 20130715

• Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

  Bioorganic & medicinal chemistry 20121115

• BreastDefend™ prevents breast-to-lung cancer metastases in an orthotopic animal model of triple-negative human breast cancer.

  Oncology reports 20121001

• Effect of diindolylmethane on Ca2+ homeostasis and viability in PC3 human prostate cancer cells.

  Journal of receptor and signal transduction research 20121001

• 3,3'-Diindolylmethane, but not indole-3-carbinol, inhibits histone deacetylase activity in prostate cancer cells.

  Toxicology and applied pharmacology 20120915

• Anti-proliferative and pro-apoptotic effects of 3,3'-diindolylmethane in human cervical cancer cells.

  Oncology reports 20120901

• Diindolylmethane-mediated Gli1 protein suppression induces anoikis in ovarian cancer cells in vitro and blocks tumor formation ability in vivo.

  The Journal of biological chemistry 20120817

• Modulation of CYP1A1, CYP1A2 and CYP1B1 expression by cabbage juices and indoles in human breast cell lines.

  Nutrition and cancer 20120801

• Diindolilmethane (DIM) selectively inhibits cancer stem cells.

  Biochemical and biophysical research communications 20120720

• Pharmacokinetic evaluation and in vitro-in vivo correlation (IVIVC) of novel methylene-substituted 3,3' diindolylmethane (DIM).

  European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20120512

• B-DIM impairs radiation-induced survival pathways independently of androgen receptor expression and augments radiation efficacy in prostate cancer.

  Cancer letters 20120501

• 3,3'-Diindolylmethane suppresses growth of human esophageal squamous cancer cells by G1 cell cycle arrest.

  Oncology reports 20120501

• Effect of the pasteurization process on the contents of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage.

  Journal of agricultural and food chemistry 20120411

• 3,3'-Diindolylmethane alters Ca2+ homeostasis and viability in MG63 human osteosarcoma cells.

  Basic & clinical pharmacology & toxicology 20120401

• Blocking epidermal growth factor receptor activation by 3,3'-diindolylmethane suppresses ovarian tumor growth in vitro and in vivo.

  The Journal of pharmacology and experimental therapeutics 20120401

• Regulation of macroautophagy in ovarian cancer cells in vitro and in vivo by controlling glucose regulatory protein 78 and AMPK.

  Oncotarget 20120401

• Regulation of Janus-activated kinase-2 (JAK2) by diindolylmethane in ovarian cancer in vitro and in vivo.

  Drug discoveries & therapeutics 20120401

• Broccoli-derived phytochemicals indole-3-carbinol and 3,3'-diindolylmethane exerts concentration-dependent pleiotropic effects on prostate cancer cells: comparison with other cancer preventive phytochemicals.

  Molecular carcinogenesis 20120301

• Synthesis and evaluation of the cytotoxicities of tetraindoles: observation that the 5-hydroxy tetraindole (SK228) induces G₂ arrest and apoptosis in human breast cancer cells.

  Journal of medicinal chemistry 20120223

• The dietary phytochemical 3,3'-diindolylmethane induces G2/M arrest and apoptosis in oral squamous cell carcinoma by modulating Akt-NF-κB, MAPK, and p53 signaling.

  Chemico-biological interactions 20120205

• Effect of diindolylmethane supplementation on low-grade cervical cytological abnormalities: double-blind, randomised, controlled trial.

  British journal of cancer 20120103

• The indolic diet-derivative, 3,3'-diindolylmethane, induced apoptosis in human colon cancer cells through upregulation of NDRG1.

  Journal of biomedicine & biotechnology 20120101

• The role of nutraceuticals in chemoprevention and chemotherapy and their clinical outcomes.

  Journal of oncology 20120101

• Novel targets for detection of cancer and their modulation by chemopreventive natural compounds.

  Frontiers in bioscience (Elite edition) 20120101

• Diindolylmethane suppresses ovarian cancer growth and potentiates the effect of cisplatin in tumor mouse model by targeting signal transducer and activator of transcription 3 (STAT3).

  BMC medicine 20120101

• Sudan III dye strongly induces CYP1A1 mRNA expression in HepG2 cells.

  Journal of biochemical and molecular toxicology 20120101

• 3,3'-Diindolylmethane increases serum interferon-γ levels in the K14-HPV16 transgenic mouse model for cervical cancer.

  In vivo (Athens, Greece) 20120101

• 3,3'-Diindolylmethane exhibits antileukemic activity in vitro and in vivo through a Akt-dependent process.

  PloS one 20120101

• Targeting bone remodeling by isoflavone and 3,3'-diindolylmethane in the context of prostate cancer bone metastasis.

  PloS one 20120101

• Loss of let-7 up-regulates EZH2 in prostate cancer consistent with the acquisition of cancer stem cell signatures that are attenuated by BR-DIM.

  PloS one 20120101

• 3,3'Diindolylmethane suppresses vascular smooth muscle cell phenotypic modulation and inhibits neointima formation after carotid injury.

  PloS one 20120101

• 3,3'-Diindolylmethane induces G1 arrest and apoptosis in human acute T-cell lymphoblastic leukemia cells.

  PloS one 20120101

• Molecular target based combinational therapeutic approaches in thyroid cancer.

  Journal of translational medicine 20120101

• A selective aryl hydrocarbon receptor modulator 3,3'-Diindolylmethane inhibits gastric cancer cell growth.

  Journal of experimental & clinical cancer research : CR 20120101

• An active product of cruciferous vegetables, 3,3'-diindolylmethane, inhibits invasive properties of extravillous cytotrophoblastic cells.

  Neuro endocrinology letters 20120101

• Activation of AMP-activated protein kinase by 3,3'-Diindolylmethane (DIM) is associated with human prostate cancer cell death in vitro and in vivo.

  PloS one 20120101

• Cancer chemoprevention by targeting the epigenome.

  Current drug targets 20111201

• 3,3'-Diindolylmethane inhibits breast cancer cell growth via miR-21-mediated Cdc25A degradation.

  Molecular and cellular biochemistry 20111201

• 3,3'-Diindolylmethane induces immunotoxicity via splenocyte apoptosis in neonatal mice.

  Toxicology letters 20111010

• 3,3'-Diindolylmethane enhances taxotere-induced growth inhibition of breast cancer cells through downregulation of FoxM1.

  International journal of cancer 20111001

• Effect of diindolylmethane on Ca(2+) movement and viability in HA59T human hepatoma cells.

  Archives of toxicology 20111001

• Antiandrogenic and growth inhibitory effects of ring-substituted analogs of 3,3'-diindolylmethane (ring-DIMs) in hormone-responsive LNCaP human prostate cancer cells.

  The Prostate 20110915

• Effects of 5,6-benzoflavone, indole-3-carbinol (I3C) and diindolylmethane (DIM) on chemically-induced mammary carcinogenesis: is DIM a substitute for I3C?

  Oncology reports 20110901

• Inactivation of AR/TMPRSS2-ERG/Wnt signaling networks attenuates the aggressive behavior of prostate cancer cells.

  Cancer prevention research (Philadelphia, Pa.) 20110901

• 3,3'-Diindolylmethane but not indole-3-carbinol activates Nrf2 and induces Nrf2 target gene expression in cultured murine fibroblasts.

  Free radical research 20110801

• Dimer radical cations of indole and indole-3-carbinol: localized and delocalized radical cations of diindolylmethane.

  The journal of physical chemistry. A 20110707

• Pharmacodynamics of dietary phytochemical indoles I3C and DIM: Induction of Nrf2-mediated phase II drug metabolizing and antioxidant genes and synergism with isothiocyanates.

  Biopharmaceutics & drug disposition 20110701

• Activation of nuclear TR3 (NR4A1) by a diindolylmethane analog induces apoptosis and proapoptotic genes in pancreatic cancer cells and tumors.

  Carcinogenesis 20110601

• Results from a dose-response study using 3,3'-diindolylmethane in the K14-HPV16 transgenic mouse model: cervical histology.

  Cancer prevention research (Philadelphia, Pa.) 20110601

• Network modeling of MDM2 inhibitor-oxaliplatin combination reveals biological synergy in wt-p53 solid tumors.

  Oncotarget 20110501

• Estrogen-like activity of perfluoroalkyl acids in vivo and interaction with human and rainbow trout estrogen receptors in vitro.

  Toxicological sciences : an official journal of the Society of Toxicology 20110301

• 3,3'-diindolylmethane modulates estrogen metabolism in patients with thyroid proliferative disease: a pilot study.

  Thyroid : official journal of the American Thyroid Association 20110301

• 3,3'-Diindolylmethane negatively regulates Cdc25A and induces a G2/M arrest by modulation of microRNA 21 in human breast cancer cells: retraction.

  Anti-cancer drugs 20110301

• 3,3'-diindolylmethane inhibits migration and invasion of human cancer cells through combined suppression of ERK and AKT pathways.

  Oncology reports 20110201

• Nitro-substituted 3,3'-bis(indolyl)methane derivatives as anion receptors: electron-withdrawing effect and tunability of anion binding properties.

  Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20110201

• Targeting NR4A1 (TR3) in cancer cells and tumors.

  Expert opinion on therapeutic targets 20110201

• 3,3'-Diindolylmethane inhibits prostate cancer development in the transgenic adenocarcinoma mouse prostate model.

  Molecular carcinogenesis 20110201

• 3,3'-Diindolylmethane decreases VCAM-1 expression and alleviates experimental colitis via a BRCA1-dependent antioxidant pathway.

  Free radical biology & medicine 20110115

• Estrogen induced metastatic modulators MMP-2 and MMP-9 are targets of 3,3'-diindolylmethane in thyroid cancer.

  PloS one 20110101

• Effect of nitric oxide on mitochondrial activity of human synovial cells.

  BMC musculoskeletal disorders 20110101

• Unfolded protein response in cancer: the physician's perspective.

  Journal of hematology & oncology 20110101

• Antitumor activity of Noscapine in combination with Doxorubicin in triple negative breast cancer.

  PloS one 20110101

• The indole-3-carbinol cyclic tetrameric derivative CTet inhibits cell proliferation via overexpression of p21/CDKN1A in both estrogen receptor-positive and triple-negative breast cancer cell lines.

  Breast cancer research : BCR 20110101

• Activation of NAG-1 via JNK signaling revealed an isochaihulactone-triggered cell death in human LNCaP prostate cancer cells.

  BMC cancer 20110101

• Of cabbages and kings.

  Gut microbes 20110101

• In vitro anti-angiogenic properties of LGD1069, a selective retinoid X-receptor agonist through down-regulating Runx2 expression on Human endothelial cells.

  BMC cancer 20110101

• Attenuation of multi-targeted proliferation-linked signaling by 3,3'-diindolylmethane (DIM): from bench to clinic.

  Mutation research 20110101

• Inhibition of fatty acid synthase and Sp1 expression by 3,3'-diindolylmethane in human breast cancer cells.

  Nutrition and cancer 20110101

• Dietary fat increases solid tumor growth and metastasis of 4T1 murine mammary carcinoma cells and mortality in obesity-resistant BALB/c mice.

  Breast cancer research : BCR 20110101

• Antiproliferative, Ultrastructural, and Physiological Effects of Amiodarone on Promastigote and Amastigote Forms of Leishmania amazonensis.

  Molecular biology international 20110101

• Enhanced anticancer activity of gemcitabine in combination with noscapine via antiangiogenic and apoptotic pathway against non-small cell lung cancer.

  PloS one 20110101

• Deletion of the aryl hydrocarbon receptor enhances the inflammatory response to Leishmania major infection.

  International journal of biological sciences 20110101

• Comparative analysis of novel and conventional Hsp90 inhibitors on HIF activity and angiogenic potential in clear cell renal cell carcinoma: implications for clinical evaluation.

  BMC cancer 20110101

• Development of derivatives of 3, 3'-diindolylmethane as potent Leishmania donovani bi-subunit topoisomerase IB poisons.

  PloS one 20110101

• Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells.

  Clinical epigenetics 20110101

• Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

  Bioorganic & medicinal chemistry letters 20101101

• Inhalation delivery of a novel diindolylmethane derivative for the treatment of lung cancer.

  Molecular cancer therapeutics 20101101

• Prostate apoptosis response-4 is expressed in normal cholangiocytes, is down-regulated in human cholangiocarcinoma, and promotes apoptosis of neoplastic cholangiocytes when induced pharmacologically.

  The American journal of pathology 20101001

• 3,3'-Diindolylmethane negatively regulates Cdc25A and induces a G2/M arrest by modulation of microRNA 21 in human breast cancer cells.

  Anti-cancer drugs 20101001

• 3,3'-Diindolylmethane (DIM) inhibits the growth and invasion of drug-resistant human cancer cells expressing EGFR mutants.

  Cancer letters 20100901

• 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 20100901

• The role of nutraceuticals in the regulation of Wnt and Hedgehog signaling in cancer.

  Cancer metastasis reviews 20100901

• Activation of checkpoint kinase 2 by 3,3'-diindolylmethane is required for causing G2/M cell cycle arrest in human ovarian cancer cells.

  Molecular pharmacology 20100801

• Assignment of UV-vis spectrum of (3,3')-diindolylmethane, a Leishmania donovani topoisomerase IB inhibitor and a candidate DNA minor groove binder.

  The journal of physical chemistry. A 20100708

• Radicals and radical ions derived from indole, indole-3-carbinol and diindolylmethane.

  The journal of physical chemistry. A 20100701

• 3,3'-diindolylmethane suppresses 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and tumor promotion in mouse skin via the downregulation of inflammatory mediators.

  Molecular carcinogenesis 20100701

• Intraocular matrix metalloproteinase 2 and 9 in patients with diabetes mellitus with and without diabetic retinopathy.

  Archives of medical science : AMS 20100630

• Anticancer properties of indole compounds: mechanism of apoptosis induction and role in chemotherapy.

  Current drug targets 20100601

• Regulation of microRNAs by natural agents: an emerging field in chemoprevention and chemotherapy research.

  Pharmaceutical research 20100601

• A new class of estrogen receptor beta-selective activators.

  Molecular interventions 20100601

• Chemopreventive properties of indole-3-carbinol, diindolylmethane and other constituents of cardamom against carcinogenesis.

  Recent patents on food, nutrition & agriculture 20100601

• The potential efficacy of 3,3'-diindolylmethane in prevention of prostate cancer development.

  European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20100501

• Concurrent inhibition of NF-kappaB, cyclooxygenase-2, and epidermal growth factor receptor leads to greater anti-tumor activity in pancreatic cancer.

  Journal of cellular biochemistry 20100501

• Generalized concentration addition predicts joint effects of aryl hydrocarbon receptor agonists with partial agonists and competitive antagonists.

  Environmental health perspectives 20100501

• Selective activation of estrogen receptor-beta target genes by 3,3'-diindolylmethane.

  Endocrinology 20100401

• 3,3'-Diindolylmethane attenuates experimental arthritis and osteoclastogenesis.

  Biochemical pharmacology 20100301

• Oral diindolylmethane (DIM): pilot evaluation of a nonsurgical treatment for cervical dysplasia.

  Gynecologic oncology 20100301

• The p38 MAPK pathway is critical for 5,5'-dibromodiindolylmethane-induced apoptosis to prevent oral squamous carcinoma cells.

  European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20100301

• Activation of nerve growth factor-induced B alpha by methylene-substituted diindolylmethanes in bladder cancer cells induces apoptosis and inhibits tumor growth.

  Molecular pharmacology 20100301

• miR-146a suppresses invasion of pancreatic cancer cells.

  Cancer research 20100215

• Ultrasound promoted rapid and green synthesis of 1,8-dioxo-octahydroxanthenes derivatives using nanosized MCM-41-SO(3)H as a nanoreactor, nanocatalyst in aqueous media.

  Ultrasonics sonochemistry 20100201

• Chemopreventive agent 3,3'-diindolylmethane selectively induces proteasomal degradation of class I histone deacetylases.

  Cancer research 20100115

• Diindolylmethane (DIM) spontaneously forms from indole-3-carbinol (I3C) during cell culture experiments.

  In vivo (Athens, Greece) 20100101

• Constitutive activation of glycogen synthase kinase-3beta correlates with better prognosis and cyclin-dependent kinase inhibitors in human gastric cancer.

  BMC gastroenterology 20100101

• Redox regulation in cancer: a double-edged sword with therapeutic potential.

  Oxidative medicine and cellular longevity 20100101

• A phase I dose-escalation study of oral BR-DIM (BioResponse 3,3'- Diindolylmethane) in castrate-resistant, non-metastatic prostate cancer.

  American journal of translational research 20100101

• Apoptotic markers in protozoan parasites.

  Parasites & vectors 20100101

• Targeting essential pathways in trypanosomatids gives insights into protozoan mechanisms of cell death.

  Parasites & vectors 20100101

• Antioxidant activity of five Brazilian plants used as traditional medicines and food in Brazil.

  Pharmacognosy magazine 20100101

• Targeting the oncogenic protein beta-catenin to enhance chemotherapy outcome against solid human cancers.

  Molecular cancer 20100101

• 1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methanes induce autophagic cell death in estrogen receptor negative breast cancer.

  BMC cancer 20100101

• Modulation of aflatoxin B1-mediated genotoxicity in primary cultures of human hepatocytes by diindolylmethane, curcumin, and xanthohumols.

  Toxicological sciences : an official journal of the Society of Toxicology 20091201

• Minireview: modulation of hormone receptor signaling by dietary anticancer indoles.

  Molecular endocrinology (Baltimore, Md.) 20091201

• Cellular signaling perturbation by natural products.

  Cellular signalling 20091101

• Harnessing the fruits of nature for the development of multi-targeted cancer therapeutics.

  Cancer treatment reviews 20091101

• Down-regulation of uPA and uPAR by 3,3'-diindolylmethane contributes to the inhibition of cell growth and migration of breast cancer cells.

  Journal of cellular biochemistry 20091101

• 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.

  International journal of oncology 20091101

• Diindolylmethane inhibits cervical dysplasia, alters estrogen metabolism, and enhances immune response in the K14-HPV16 transgenic mouse model.

  Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20091101

• Novel 3,3'-diindolylmethane derivatives: synthesis and cytotoxicity, structural characterization in solid state.

  European journal of medicinal chemistry 20091001

• 3,3'-Diindolylmethane induces a G(1) arrest in human prostate cancer cells irrespective of androgen receptor and p53 status.

  Biochemical pharmacology 20090901

• A controlled safety study of diindolylmethane in the immature rat model.

  The Laryngoscope 20090901

• 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 research 20090815

• 3,3'-diindolylmethane attenuates colonic inflammation and tumorigenesis in mice.

  Inflammatory bowel diseases 20090801

• Low concentrations of diindolylmethane, a metabolite of indole-3-carbinol, protect against oxidative stress in a BRCA1-dependent manner.

  Cancer research 20090801

• Relevance of the aryl hydrocarbon receptor (AhR) for clinical toxicology.

  Clinical toxicology (Philadelphia, Pa.) 20090801

• Regioselective synthesis and biological evaluation of bis(indolyl)methane derivatized 1,4-disubstituted 1,2,3-bistriazoles as anti-infective agents.

  Bioorganic & medicinal chemistry letters 20090701

• 3,3'-Diindolylmethane enhances chemosensitivity of multiple chemotherapeutic agents in pancreatic cancer.

  Cancer research 20090701

• Sensitization of squamous cell carcinoma to cisplatin induced killing by natural agents.

  Cancer letters 20090618

• Inactivation of uPA and its receptor uPAR by 3,3'-diindolylmethane (DIM) leads to the inhibition of prostate cancer cell growth and migration.

  Journal of cellular biochemistry 20090601

• Estrogen receptor subtype- and promoter-specific modulation of aryl hydrocarbon receptor-dependent transcription.

  Molecular cancer research : MCR 20090601

• 3,3'-diindolylmethane induction of p75NTR-dependent cell death via the p38 mitogen-activated protein kinase pathway in prostate cancer cells.

  Cancer prevention research (Philadelphia, Pa.) 20090601

• 3,3'-diindolylmethane enhances the efficacy of butyrate in colon cancer prevention through down-regulation of survivin.

  Cancer prevention research (Philadelphia, Pa.) 20090601

• Exploring bis-(indolyl)methane moiety as an alternative and innovative CAP group in the design of histone deacetylase (HDAC) inhibitors.

  Bioorganic & medicinal chemistry letters 20090515

• 3,3'-Diindolylmethane enhances taxotere-induced apoptosis in hormone-refractory prostate cancer cells through survivin down-regulation.

  Cancer research 20090515

• Lipid G protein-coupled receptor ligand identification using beta-arrestin PathHunter assay.

  The Journal of biological chemistry 20090501

• Enhancement of chemically-induced HL-60 cell differentiation by 3,3'-diindolylmethane derivatives.

  Chemical & pharmaceutical bulletin 20090501

• Cell cycle-dependent effects of 3,3'-diindolylmethane on proliferation and apoptosis of prostate cancer cells.

  Journal of cellular physiology 20090401

• Effect of boiling on the content of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage.

  Journal of agricultural and food chemistry 20090325

• Toxic and chemopreventive ligands preferentially activate distinct aryl hydrocarbon receptor pathways: implications for cancer prevention.

  Cancer prevention research (Philadelphia, Pa.) 20090301

• Enhancement of docetaxel anticancer activity by a novel diindolylmethane compound in human non-small cell lung cancer.

  Clinical cancer research : an official journal of the American Association for Cancer Research 20090115

• Suppression of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced nitric-oxide synthase 2 expression in astrocytes by a novel diindolylmethane analog protects striatal neurons against apoptosis.

  Molecular pharmacology 20090101

• Targeting of aryl hydrocarbon receptor-mediated activation of cyclooxygenase-2 expression by the indole-3-carbinol metabolite 3,3'-diindolylmethane in breast cancer cells.

  The Journal of nutrition 20090101

• Modulation of CXCR4, CXCL12, and Tumor Cell Invasion Potential In Vitro by Phytochemicals.

  Journal of oncology 20090101

• Induction of G1 and G2/M cell cycle arrests by the dietary compound 3,3'-diindolylmethane in HT-29 human colon cancer cells.

  BMC gastroenterology 20090101

• A combination of indol-3-carbinol and genistein synergistically induces apoptosis in human colon cancer HT-29 cells by inhibiting Akt phosphorylation and progression of autophagy.

  Molecular cancer 20090101

• The dietary phytochemical indole-3-carbinol is a natural elastase enzymatic inhibitor that disrupts cyclin E protein processing.

  Proceedings of the National Academy of Sciences of the United States of America 20081216

• 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.

  Molecular pharmacology 20081101

• Cancer chemotherapy with indole-3-carbinol, bis(3'-indolyl)methane and synthetic analogs.

  Cancer letters 20081008

• Single-dose pharmacokinetics and tolerability of absorption-enhanced 3,3'-diindolylmethane in healthy subjects.

  Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20081001

• Chemoprevention of pancreatic cancer: characterization of Par-4 and its modulation by 3,3' diindolylmethane (DIM).

  Pharmaceutical research 20080901

• 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 and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080701

• CXCR4 and CXCL12 down-regulation: a novel mechanism for the chemoprotection of 3,3'-diindolylmethane for breast and ovarian cancers.

  Cancer letters 20080628

• 1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methanes inhibit colon cancer cell and tumor growth through activation of c-jun N-terminal kinase.

  Carcinogenesis 20080601

• Apoptosis-inducing effect of erlotinib is potentiated by 3,3'-diindolylmethane in vitro and in vivo using an orthotopic model of pancreatic cancer.

  Molecular cancer therapeutics 20080601

• 3,3'-Diindolylmethane stimulates murine immune function in vitro and in vivo.

  The Journal of nutritional biochemistry 20080501

• 3,3'-diindolylmethane reduces levels of HIF-1alpha and HIF-1 activity in hypoxic cultured human cancer cells.

  Biochemical pharmacology 20080501

• 1,1-bis(3'-indolyl)-1-(p-methoxyphenyl)methane activates Nur77-independent proapoptotic responses in colon cancer cells.

  Molecular carcinogenesis 20080401

• Mammalian target of rapamycin repression by 3,3'-diindolylmethane inhibits invasion and angiogenesis in platelet-derived growth factor-D-overexpressing PC3 cells.

  Cancer research 20080315

• [3,3-diindolylmethane enhances the inhibitory effect of idarubicin on the growth of human prostate cancer cells].

  Zhonghua yi xue za zhi 20080311

• Screening of synthetic and plant-derived compounds for (anti)estrogenic and (anti)androgenic activities.

  Analytical and bioanalytical chemistry 20080201

• Induction of growth arrest and apoptosis in human breast cancer cells by 3,3-diindolylmethane is associated with induction and nuclear localization of p27kip.

  Molecular cancer therapeutics 20080201

• An insight into the mechanism of inhibition of unusual bi-subunit topoisomerase I from Leishmania donovani by 3,3'-di-indolylmethane, a novel DNA topoisomerase I poison with a strong binding affinity to the enzyme.

  The Biochemical journal 20080115

• Comparative study of aryl hydrocarbon receptor ligand activities of six chemicals in vitro and in vivo.

  Archives of toxicology 20080101

• Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor.

  The Journal of steroid biochemistry and molecular biology 20080101

• Expression and clinical significance of glucose regulated proteins GRP78 (BiP) and GRP94 (GP96) in human adenocarcinomas of the esophagus.

  BMC cancer 20080101

• The first generation of a BAC-based physical map of Brassica rapa.

  BMC genomics 20080101

• Review. Indole-3-carbinol as a chemoprotective agent in breast and prostate cancer.

  In vivo (Athens, Greece) 20080101

• Biological and functional analysis of statistically significant pathways deregulated in colon cancer by using gene expression profiles.

  International journal of biological sciences 20080101

• Biological processes, properties and molecular wiring diagrams of candidate low-penetrance breast cancer susceptibility genes.

  BMC medical genomics 20080101

• Extended treatment with physiologic concentrations of dietary phytochemicals results in altered gene expression, reduced growth, and apoptosis of cancer cells.

  Molecular cancer therapeutics 20071101

• Inactivation of NF-kappaB by 3,3'-diindolylmethane contributes to increased apoptosis induced by chemotherapeutic agent in breast cancer cells.

  Molecular cancer therapeutics 20071001

• Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.

  Bioorganic & medicinal chemistry letters 20070901

• Predicting the physiological relevance of in vitro cancer preventive activities of phytochemicals.

  Acta pharmacologica Sinica 20070901

• Computer-aided rational drug design: a novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signaling.

  Journal of medicinal chemistry 20070726

• 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.

  The Journal of biological chemistry 20070720

• Gene expression analysis during tumor enhancement by the dietary phytochemical, 3,3'-diindolylmethane, in rainbow trout.

  Carcinogenesis 20070701

• Quantitative combination effects between sulforaphane and 3,3'-diindolylmethane on proliferation of human colon cancer cells in vitro.

  Carcinogenesis 20070701

• 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 research 20070701

• A review of the clinical efficacy and safety of cruciferous vegetable phytochemicals.

  Nutrition reviews 20070601

• 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 research 20070401

• Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis.

  Pharmacological research 20070301

• Combination of tunicamycin with anticancer drugs synergistically enhances their toxicity in multidrug-resistant human ovarian cystadenocarcinoma cells.

  Cancer cell international 20070101

• Interplay of genes regulated by estrogen and diindolylmethane in breast cancer cell lines.

  Molecular medicine (Cambridge, Mass.) 20070101

• 1,1-Bis(3'-indolyl)-1-(p-biphenyl)methane inhibits basal-like breast cancer growth in athymic nude mice.

  Breast cancer research : BCR 20070101

• Gene expression profiling reveals effects of Cimicifuga racemosa (L.) NUTT. (black cohosh) on the estrogen receptor positive human breast cancer cell line MCF-7.

  BMC pharmacology 20070101

• Curcumin enhances the apoptosis-inducing potential of TRAIL in prostate cancer cells: molecular mechanisms of apoptosis, migration and angiogenesis.

  Journal of molecular signaling 20070101

• Single-dose and multiple-dose administration of indole-3-carbinol to women: pharmacokinetics based on 3,3'-diindolylmethane.

  Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20061201

• Fas-mediated apoptosis in cholangiocarcinoma cells is enhanced by 3,3'-diindolylmethane through inhibition of AKT signaling and FLICE-like inhibitory protein.

  The American journal of pathology 20061101

• 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 research 20061015

• Estrogen receptor alpha as a target for indole-3-carbinol.

  The Journal of nutritional biochemistry 20061001

• Aryl hydrocarbon receptor agonists directly activate estrogen receptor alpha in MCF-7 breast cancer cells.

  Biological chemistry 20060901

• Comparison of growth inhibition profiles and mechanisms of apoptosis induction in human colon cancer cell lines by isothiocyanates and indoles from Brassicaceae.

  Mutation research 20060725

• Inhibition of breast cancer cell growth and induction of cell death by 1,1-bis(3'-indolyl)methane (DIM) and 5,5'-dibromoDIM.

  Cancer letters 20060518

• 3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells.

  The Journal of surgical research 20060515

• 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 research 20060501

• Gene expression profiling revealed survivin as a target of 3,3'-diindolylmethane-induced cell growth inhibition and apoptosis in breast cancer cells.

  Cancer research 20060501

• 3,3'-diindolylmethane (DIM) and its derivatives induce apoptosis in pancreatic cancer cells through endoplasmic reticulum stress-dependent upregulation of DR5.

  Carcinogenesis 20060401

• Synthetic dimer of indole-3-carbinol: second generation diet derived anti-cancer agent in hormone sensitive prostate cancer.

  The Prostate 20060401

• 3,3'-diindolylmethane is a novel topoisomerase IIalpha catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells.

  Molecular pharmacology 20060401

• Chemoprevention of cervical cancer.

  Best practice & research. Clinical obstetrics & gynaecology 20060401

• Indole-3-carbinol, but not its major digestive product 3,3'-diindolylmethane, induces reversible hepatocyte hypertrophy and cytochromes P450.

  Toxicology and applied pharmacology 20060301

• Toxicogenomic profiling of the hepatic tumor promoters indole-3-carbinol, 17beta-estradiol and beta-naphthoflavone in rainbow trout.

  Toxicological sciences : an official journal of the Society of Toxicology 20060301

• Inhibition of growth factor-induced Ras signaling in vascular endothelial cells and angiogenesis by 3,3'-diindolylmethane.

  Carcinogenesis 20060301

• Using salmonid microarrays to understand the dietary modulation of carcinogenesis in rainbow trout.

  Toxicological sciences : an official journal of the Society of Toxicology 20060301

• Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells.

  Chemical research in toxicology 20060301

• Multiple, disparate roles for calcium signaling in apoptosis of human prostate and cervical cancer cells exposed to diindolylmethane.

  Molecular cancer therapeutics 20060301

• BRCA1 and BRCA2 as molecular targets for phytochemicals indole-3-carbinol and genistein in breast and prostate cancer cells.

  British journal of cancer 20060213

• 3,3'-Diindolylmethane downregulates pro-survival pathway in hormone independent prostate cancer.

  Biochemical and biophysical research communications 20060210

• Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells.

  Molecular pharmacology 20060201

• Oxidized bis(indolyl)methane: a simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode.

  Organic letters 20060119

• The natural chemopreventive compound indole-3-carbinol: state of the science.

  In vivo (Athens, Greece) 20060101

• Multifocal angiostatic therapy: an update.

  Integrative cancer therapies 20051201

• Down-regulation of c-FLIP contributes to the sensitization effect of 3,3'-diindolylmethane on TRAIL-induced apoptosis in cancer cells.

  Molecular cancer therapeutics 20051201

• 3,3'-Diindolylmethane, a cruciferous vegetable derived synthetic anti-proliferative compound in thyroid disease.

  Biochemical and biophysical research communications 20051125

• Indole-3-carbinol inhibition of androgen receptor expression and downregulation of androgen responsiveness in human prostate cancer cells.

  Carcinogenesis 20051101

• [Current therapeutic options for recurrent respiratory papillomatosis].

  HNO 20051101

• Molecular targets of dietary polyphenols with anti-inflammatory properties.

  Yonsei medical journal 20051031

• Gateways to clinical trials.

  Methods and findings in experimental and clinical pharmacology 20051001

• Molecular targets and anticancer potential of indole-3-carbinol and its derivatives.

  Cell cycle (Georgetown, Tex.) 20050901

• Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro.

  Journal of agricultural and food chemistry 20050518

• 3,3'-Diindolylmethane inhibits angiogenesis and the growth of transplantable human breast carcinoma in athymic mice.

  Carcinogenesis 20050401

• DIM stimulates IFNgamma gene expression in human breast cancer cells via the specific activation of JNK and p38 pathways.

  Oncogene 20050331

• A comparison of two methods to determine the solubility of compounds in aerosol propellants.

  International journal of pharmaceutics 20050323

• Indole-3-carbinol (I3C) inhibits cyclin-dependent kinase-2 function in human breast cancer cells by regulating the size distribution, associated cyclin E forms, and subcellular localization of the CDK2 protein complex.

  The Journal of biological chemistry 20050311

• Indole-3-carbinol and 3,3'-diindolylmethane induce expression of NAG-1 in a p53-independent manner.

  Biochemical and biophysical research communications 20050304

• By the way, doctor. A preventive doctor told me to take indolplex (bioavailable diindolylmethane or DIM) to aid estrogen metabolism. Is there any research available about this supplement?

  Harvard women's health watch 20050201

• Red maca (Lepidium meyenii) reduced prostate size in rats.

  Reproductive biology and endocrinology : RB&E 20050101

• Inhibition of nuclear translocation of nuclear factor-{kappa}B contributes to 3,3'-diindolylmethane-induced apoptosis in breast cancer cells.

  Cancer research 20050101

• Peroxisome proliferator-activated receptor gamma-dependent activation of p21 in Panc-28 pancreatic cancer cells involves Sp1 and Sp4 proteins.

  Endocrinology 20041201

• Lack of antagonism of 2,3,7,8-tetrachlorodibenzo-p-dioxin's (TCDDs) induction of cytochrome P4501A1 (CYP1A1) by the putative selective aryl hydrocarbon receptor modulator 6-alkyl-1,3,8-trichlorodibenzofuran (6-MCDF) in the mouse hepatoma cell line Hepa-1c1c7.

  Chemico-biological interactions 20041120

• Cell signaling pathways altered by natural chemopreventive agents.

  Mutation research 20041102

• Dietary agent indole-3-carbinol protects female rats against the hepatotoxicity of the antitumor drug ET-743 (trabectidin) without compromising efficacy in a rat mammary carcinoma.

  International journal of cancer 20041010

• Induction of apoptosis in human prostate cancer cell line, PC3, by 3,3'-diindolylmethane through the mitochondrial pathway.

  British journal of cancer 20041004

• Therapeutic activity of 3,3'-diindolylmethane on prostate cancer in an in vivo model.

  The Prostate 20041001

• 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 research 20040901

• Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice.

  Clinical cancer research : an official journal of the American Association for Cancer Research 20040801

• Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes.

  Xenobiotica; the fate of foreign compounds in biological systems 20040701

• Physiological modeling of formulated and crystalline 3,3'-diindolylmethane pharmacokinetics following oral administration in mice.

  Drug metabolism and disposition: the biological fate of chemicals 20040601

• Anticarcinogenic and antioxidant activity of diindolylmethane derivatives.

  Acta pharmacologica Sinica 20040501

• 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.

  Molecular cancer therapeutics 20040301

• Endoplasmic reticulum stress as a correlate of cytotoxicity in human tumor cells exposed to diindolylmethane in vitro.

  Cell stress & chaperones 20040301

• 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.

  Molecular endocrinology (Baltimore, Md.) 20040201

• 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 detection and prevention 20040101

• Pilot study: effect of 3,3'-diindolylmethane supplements on urinary hormone metabolites in postmenopausal women with a history of early-stage breast cancer.

  Nutrition and cancer 20040101

• New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.

  Journal of natural products 20031101

• Arsenate reduction in human erythrocytes and rats--testing the role of purine nucleoside phosphorylase.

  Toxicological sciences : an official journal of the Society of Toxicology 20030701

• Evaluation of chronic dietary exposure to indole-3-carbinol and absorption-enhanced 3,3'-diindolylmethane in sprague-dawley rats.

  Toxicological sciences : an official journal of the Society of Toxicology 20030701

• Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells.

  The Journal of biological chemistry 20030606

• Indole-3-carbinol and 3,3'-diindolylmethane induce apoptosis in human prostate cancer cells.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030601

• Liquid chromatographic assay for the simultaneous determination of indole-3-carbinol and its acid condensation products in plasma.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030425

• Effect of chemopreventive compounds from Brassica vegetables on NAD(P)H:quinone reductase and induction of DNA strand breaks in murine hepa1c1c7 cells.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030401

• Effects of treatment of rats with indole-3-carbinol on apoptosis in the mammary gland and mammary adenocarcinomas.

  Anticancer research 20030101

• Increased arylhydrocarbon receptor expression offers a potential therapeutic target for pancreatic cancer.

  Oncogene 20020905

• 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 20020801

• Estrogen metabolism and the diet-cancer connection: rationale for assessing the ratio of urinary hydroxylated estrogen metabolites.

  Alternative medicine review : a journal of clinical therapeutic 20020401

• Bcl-2 family-mediated apoptotic effects of 3,3'-diindolylmethane (DIM) in human breast cancer cells.

  Biochemical pharmacology 20020315

• Therapy for recurrent respiratory papillomatosis.

  Antiviral therapy 20020301

• Fate of indole-3-carbinol in cultured human breast tumor cells.

  Chemical research in toxicology 20020201

• 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 20011101

• Involvement of a post-transcriptional mechanism in the inhibition of CYP1A1 expression by resveratrol in breast cancer cells.

  Biochemical pharmacology 20011015

• 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 research 20010815

• 2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells.

  Toxicological sciences : an official journal of the Society of Toxicology 20010501

• Methyl-substituted diindolylmethanes as inhibitors of estrogen-induced growth of T47D cells and mammary tumors in rats.

  Breast cancer research and treatment 20010301

• 3,3'-diindolylmethane, a major condensation product of indole-3-carbinol, is a potent estrogen in the rainbow trout.

  Toxicology and applied pharmacology 20010201

• Identification of estrogen-induced genes downregulated by AhR agonists in MCF-7 breast cancer cells using suppression subtractive hybridization.

  Gene 20010110

• Concurrent flavin-containing monooxygenase down regulation and cytochrome P450 induction by dietary indoles in the rat: implication for drug-drug interactions.

  Advances in experimental medicine and biology 20010101

• Quantitative determination of 3,3'-diindolylmethane in urine of individuals receiving indole-3-carbinol.

  Nutrition and cancer 20010101

• Aryl hydrocarbon receptor-mediated antiestrogenic and antitumorigenic activity of diindolylmethane.

  Carcinogenesis 19980901

• Ah receptor binding properties of indole carbinols and induction of hepatic estradiol hydroxylation.

  Biochemical pharmacology 19930309