3,3'-Diindolylmethane - CAS 1968-05-4
Catalog number: B0084-289521
Category: Inhibitor
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Molecular Formula:
C17H14N2
Molecular Weight:
246.31
COA:
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Targets:
Checkpoint Kinase (Chk)
Description:
3,3'-Diindolylmethane is an activator of checkpoint kinase 2 (Chk2) that induces G2/M cell cycle arrest in various cancer cell lines. It is used as an antineoplastic agent.
Nutritional supplement in health care products.
Brife Description:
Chk2 activator
Purity:
≥99% by HPLC
Appearance:
White to Pale Beige Solid
Synonyms:
DIM; Di(1H-indol-3-yl)methane; Diindolylmethane; 3,3'-Methylenediindole; 3,3'-Methylenebis-1H-indole
MSDS:
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Application:
Ingredient of health care products.
Melting Point:
161-163°C (dec.)
InChIKey:
VFTRKSBEFQDZKX-UHFFFAOYSA-N
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
Canonical SMILES:
C1=CC=C2C(=C1)C(=CN2)CC3=CNC4=CC=CC=C43
1.1,1-Bis (3'-indolyl)-1-(p-substitutedphenyl)methane compounds inhibit lung cancer cell and tumor growth in a metastasis model.
Andey T1, Patel A, Jackson T, Safe S, Singh M. Eur J Pharm Sci. 2013 Oct 9;50(2):227-41. doi: 10.1016/j.ejps.2013.07.007. Epub 2013 Jul 23.
1,1-Bis(3-indolyl)-1-(p-substitutedphenyl)methane (C-DIM) compounds exhibit remarkable antitumor activity with low toxicity in various cancer cells including lung tumors. Two C-DIM analogs, DIM-C-pPhOCH3 (C-DIM-5) and DIM-C-pPhOH (C-DIM-8) while acting differentially on the orphan nuclear receptor, TR3/Nur77 inhibited cell cycle progression from G0/G1 to S-phase and induced apoptosis in A549 cells. Combinations of docetaxel (doc) with C-DIM-5 or C-DIM-8 showed synergistic anticancer activity in vitro and these results were consistent with their enhanced antitumor activities invivo. Respirable aqueous formulations of C-DIM-5 (mass median aerodynamic diameter of 1.92±0.22μm and geometric standard deviation of 2.31±0.12) and C-DIM-8 (mass median aerodynamic diameter of 1.84±0.31μm and geometric standard deviation of 2.11±0.15) were successfully delivered by inhalation to athymic nude mice bearing A549 cells as metastatic tumors. This resulted in significant (p<0.
2.Cancer chemotherapy with indole-3-carbinol, bis(3'-indolyl)methane and synthetic analogs.
Safe S1, Papineni S, Chintharlapalli S. Cancer Lett. 2008 Oct 8;269(2):326-38. doi: 10.1016/j.canlet.2008.04.021. Epub 2008 May 22.
Indole-3-carbinol (I3C) conjugates are phytochemicals expressed in brassica vegetables and have been associated with the anticancer activities of vegetable consumption. I3C and its metabolite bis(3'-indolyl)methane (DIM) induce overlapping and unique responses in multiple cancer cell lines and tumors, and these include growth inhibition, apoptosis and antiangiogenic activities. The mechanisms of these responses are complex and dependent on cell context. I3C and/or DIM activate or inactivate multiple nuclear receptors, induce endoplasmic reticulum stress, decrease mitochondrial membrane potential, and modulate multiple signaling pathways including kinases. DIM has been used as a template to synthesize a series of 1,1-bis(3'indolyl)-1-(substituted aromatic)methanes (i.e. C-DIMs) which are also cytotoxic to cancer cells and tumors. Some of the effects of C-DIMs resemble those reported for DIM analogs; however, structure-activity studies with the aromatic ring has resulted in generation of highly unique receptor agonists.
3.1,1-Bis(3'-indolyl)-1-(p-substitutedphenyl)methanes induce peroxisome proliferator-activated receptor gamma-mediated growth inhibition, transactivation, and differentiation markers in colon cancer cells.
Chintharlapalli S1, Smith R 3rd, Samudio I, Zhang W, Safe S. Cancer Res. 2004 Sep 1;64(17):5994-6001.
1,1-Bis(3'indolyl)-1-(p-substitutedphenyl)methanes containing p-trifluoromethyl (DIM-C-pPhCF)), p-t-butyl (DIM-C-pPhtBu), and p-phenyl (DIM-C-pPhC6H5) groups induce peroxisome proliferator-activated receptor gamma (PPARgamma)-mediated transactivation in HT-29, HCT-15, RKO, and SW480 colon cancer cell lines. Rosiglitazone also induces transactivation in these cell lines and inhibited growth of HT-29 cells, which express wild-type PPARgamma but not HCT-15 cells, which express mutant (K422Q) PPARgamma. In contrast, DIM-C-pPhCF3, DIM-C-pPhtBu, and DIM-C-pPhC6H5 inhibited growth of both HT-29 and HCT-15 cells with IC50 values ranging from 1 to 10 micromol/L. Rosiglitazone and diindolylmethane (DIM) analogues did not affect expression of cyclin D1, p21, or p27 protein levels or apoptosis in HCT-15 or HT-29 cells but induced keratin 18 in both cell lines. However, rosiglitazone induced caveolins 1 and 2 in HT-29 but not HCT-15 cells, whereas these differentiation markers were induced by DIM-C-pPhCF3 and DIM-C-pPhC6H5 in both cell lines.
4.Peroxisome proliferator-activated receptor gamma-dependent activity of indole ring-substituted 1,1-bis(3'-indolyl)-1-(p-biphenyl)methanes in cancer cells.
Guo J1, Chintharlapalli S, Lee SO, Cho SD, Lei P, Papineni S, Safe S. Cancer Chemother Pharmacol. 2010 May;66(1):141-50. doi: 10.1007/s00280-009-1144-0. Epub 2009 Oct 13.
PURPOSE: 1,1-Bis(3-indolyl)-1-(p-substituted phenyl)methanes (C-DIMs) substituted in the phenyl ring with a para-, t-butyl, trifluoromethyl (DIM-C-pPhCF(3)) or phenyl (DIM-C-pPhC(6)H(5)) group activate peroxisome proliferator-activated receptor gamma (PPARgamma) in several cancer cell lines, and DIM-C-pPhCF(3) also activates the orphan receptor Nur77. In this study, we have examined the effects of 5,5'-dihydroxy, 5,5'-dimethyl, 5,5'-dibromo, 5,5'-dinitro and 5,5'-dimethoxyindole ring-substituted analogs of DIM-C-pPhC(6)H(5) on their activity as PPARgamma agonists.
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CAS 1968-05-4 3,3'-Diindolylmethane

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