Home Other Building Blocks 3,3'-Diindolylmethane

3,3'-Diindolylmethane

CAS No.:
1968-05-4
Catalog Number:
AG003BAM
Molecular Formula:
C17H14N2
Molecular Weight:
246.3065
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5g
97%
In Stock USA
United States
$13
- +
25g
97%
In Stock USA
United States
$29
- +
100g
97%
In Stock USA
United States
$75
- +
500g
97%
In Stock USA
United States
$350
- +
Product Description
Catalog Number:
AG003BAM
Chemical Name:
3,3'-Diindolylmethane
CAS Number:
1968-05-4
Molecular Formula:
C17H14N2
Molecular Weight:
246.3065
MDL Number:
MFCD00195766
IUPAC Name:
3-(1H-indol-3-ylmethyl)-1H-indole
InChI:
InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
InChI Key:
VFTRKSBEFQDZKX-UHFFFAOYSA-N
SMILES:
c1ccc2c(c1)c(c[nH]2)Cc1c[nH]c2c1cccc2
EC Number:
606-355-3
UNII:
SSZ9HQT61Z
NSC Number:
708486
Properties
Complexity:
286  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
246.116g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
0
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
246.313g/mol
Monoisotopic Mass:
246.116g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
31.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.3  
Literature
Title Journal
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
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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
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