Category: 1968-05-4

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Therapeutic potential of aryl hydrocarbon receptor ligands derived from natural products in rheumatoid arthritis, published in 2020-06-30, which mentions a compound: 1968-05-4, mainly applied to review aryl hydrocarbon receptor ligand natural product rheumatoid arthritis; aryl hydrocarbon receptor; ligands; natural products; rheumatoid arthritis; therapeutic potential, Synthetic Route of C17H14N2.

A review. Rheumatoid arthritis is an autoimmune-mediated inflammatory disease, which is characterized by chronic synovitis, progressive bone destruction and reduced mobility. Aryl hydrocarbon receptor (AhR), a ligand-dependent transcription factor, has been shown to regulate the differentiation, activation and apoptosis of various cells involved in rheumatoid arthritis. The ligands of AhR such as tetrachlorodibenzo-p-dioxin, benzo[a]pyrene and 3,3′-diindolylmetheane are able to inhibit osteoclastogenesis and attenuate arthritis in mice. However, the long-term use of these compounds is associated with severe side effects, which limit their use as therapeutic agents in animals or humans. There is an urgent need to search for new AhR ligands that are effective and safe. This MiniReview discusses the potential therapeutic value of the AhR ligands derived from natural products.

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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Name: 3,3′-Diindolylmethane. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 3,3′-Diindolylmethane, is researched, Molecular C17H14N2, CAS is 1968-05-4, about Strain-specific altered nicotine metabolism in 3,3′-diindolylmethane (DIM) exposed mice. Author is Bloom, A. Joseph; Upadhyaya, Pramod; Kharasch, Evan D..

Two indole compounds, indole-3-carbinol (I3C) and its acid condensation product, 3,3′-diindolymethane (DIM), have been shown to suppress the expression of flavin-containing monooxygenases (FMO) and to induce some hepatic cytochrome P450s (CYPs) in rats. In liver microsomes prepared from rats fed I3C or DIM, FMO-mediated nicotine N-oxygenation was decreased, whereas CYP-mediated nicotine metabolism to nicotine iminium and subsequently to cotinine was unchanged. Therefore, it was hypothesized that in mice DIM would also suppress nicotine N-oxygenation without affecting CYP-mediated nicotine metabolism Liver microsomes were produced from male and female C57BL/6 J and CD1 mice fed 2500 ppm (ppm) DIM for 14 days. In liver microsomes from DIM-fed mice, FMO-mediated nicotine N-oxygenation did not differ from the controls, but CYP-mediated nicotine metabolism was significantly increased, with results varying by sex and strain. To confirm the effects of DIM in vivo, control and DIM-fed CD1 male mice were injected s.c. with nicotine, and the plasma concentrations of nicotine, cotinine and nicotine-N-oxide were measured over 30 min. The DIM-fed mice showed greater cotinine concentrations compared with the controls 10 min following injection. It is concluded that the effects of DIM on nicotine metabolism in vitro and in vivo differ between mice and rats and between mouse strains, and that DIM is an effective inducer of CYP-mediated nicotine metabolism in commonly studied mouse strains.

Here is just a brief introduction to this compound(1968-05-4)Name: 3,3′-Diindolylmethane, more information about the compound(3,3′-Diindolylmethane) is in the article, you can click the link below.

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Chloride – Wikipedia,
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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Modulatory Effect of Indoles on the Expression of miRNAs Regulating G1/S Cell Cycle Phase in Breast Cancer Cells, published in 2020-12-31, which mentions a compound: 1968-05-4, Name is 3,3′-Diindolylmethane, Molecular C17H14N2, Safety of 3,3′-Diindolylmethane.

Indole-3-carbinol (I3C) is a naturally occurring glucosinolate found in Brassica vegetables that is usually converted in gastric acidic environment to the efficient metabolite 3,3′-diindolylmethane (DIM). Both indoles (I3C and DIM) are known chemopreventive agents for various cancers including breast cancer. This study aimed to investigate the influence of both indoles on the tumor suppressor miRNAs (let-7a-e, miR-15a, miR-16, miR-17-5p, miR-19a, and miR-20a) and oncomiRs (miR-181a, miR-181b, miR-210, miR-221, and miR-106a), which are controlling the cell cycle key regulators: cyclin-dependent kinases (CDKs), CDK inhibitor p27Kip1, and cyclin D1. Our results indicated that both indoles generally elevated the expression of the tumor suppressor miRNAs let-7a-e, miR-19a, miR-17-5p, and miR-20a and decreased the expression of the oncomiR list. Both indoles were able to significantly suppress the expression of CDK4 and CDK6 as well as the apoptotic markers Bcl-2 and survivin. Both indoles decreased cyclin-D1 protein, where I3C decreased cytoplasmic and nuclear cyclin-D1 significantly. Cytoplasmic and nuclear P27Kip1 showed overexpression following treatment with I3C higher than that detected following DIM treatment. This study provides a mechanistic elucidation of the previously reported cell cycle arrest by I3C and DIM in breast cancer cells suggesting that this effect could be through modulation of miRNAs expression that, in turn, regulates the genetic network controlling the G1/S phase in cell cycle progression.

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Chloride – Wikipedia,
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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Amelioration of whole abdominal irradiation-induced intestinal injury in mice with 3,3′-Diindolylmethane (DIM), published in 2019-01-31, which mentions a compound: 1968-05-4, mainly applied to radioprotective diindolylmethane abdominal irradiation intestinal injury; Gastrointestinal tract; Intestinal flora; Ionizing radiation; NFE2L2/NRF2; Reactive oxygen species (ROS); Small intestine, Electric Literature of C17H14N2.

Ionizing radiation-induced intestinal injury is a catastrophic disease with limited effective therapies. 3,3′-Diindolylmethane (DIM), a potent antioxidant agent, has previously been shown to ameliorate hematopoietic injury in a murine model of total body radiation injury, but its effects on ionizing radiation-induced intestinal damage are not clear. Here, we demonstrate that administration of DIM not only protects mice against whole abdominal irradiation (WAI)-induced lethality and weight loss but also ameliorates crypt-villus structural and functional injury of the small intestine. In addition, treatment with DIM significant enhances WAI-induced reductions in Lgr5+ ISCs and their progeny cells, including lysozyme+ Paneth cells, Villin+ enterocytes and Ki67+ instantaneous amplifying cells, thus promoting small intestine repair following WAI exposure. Notably, the expression of Nrf2 increased, while the number of apoptotic cells and the expression of γH2AX decreased in the small intestines of DIM-treated mice compared to mice treated with vehicle following WAI. In vitro, we demonstrated that DIM protected human intestinal epithelial cell-6 (HIEC-6) against ionizing radiation, leading to increased cell vitality. Mechanistically, the radioprotective effect of DIM was likely attributable to its anti-DNA damage effects in irradiated HIEC-6 cells. Moreover, these changes were related to reduction in reactive oxygen species (ROS) levels and increased the activities of antioxidant enzymic in irradiated HIEC-6 cells. Addnl., the DIM radioprotective effects on the intestine resulted in the restoration of the WAI-shifted gut bacteria composition in mice. Collectively, our findings demonstrate that the beneficial properties of DIM mitigate intestinal radiation injury, which provides a novel strategy for improving the therapeutic effects of irradiation-induced intestinal injury.

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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Safety of 3,3′-Diindolylmethane. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3,3′-Diindolylmethane, is researched, Molecular C17H14N2, CAS is 1968-05-4, about Physicochemical and microstructural properties of polymerized whey protein encapsulated 3,3′-diindolylmethane nanoparticles. Author is Khan, Abbas; Wang, Cuina; Sun, Xiaomeng; Killpartrick, Adam; Guo, Mingruo.

The fat-soluble antioxidant 3,3′-diindolylmethane (DIM), is a natural phytochem. found in Brassica vegetables, such as cabbage, broccoli, and Brussels sprouts. The stability of this compound is a major challenge for its applications. Polymerized whey protein (PWP)-based DIM nanoparticles were prepared at different mass ratios of protein and DIM by mixing PWP and DIM followed by ultrasound treatment for 4 min. All the nanoparticles were studied for particle size, zeta potential, rheol. and microstructural properties, and storage stability. The mean particle size of the PWP-based nanoparticles was significantly increased (p < 0.05) by the addition of DIM at different mass ratios, ranging from 241.33 ± 14.82 to 270.57 ± 15.28 nm. Zeta potential values of all nanoparticles were highly neg. (greater than ±30 mV), suggesting a stable solution due its electrostatic repulsive forces. All samples exhibited shear thinning behavior (n < 1), fitted with Sisko model (R2 > 0.997). Fourier Transform IR (FTIR)spectra revealed that the secondary structure was changed and the absorption intensity for hydrogen bonding got stronger by further incorporating DIM into PWP. Transmission electronic microscopy (TEM) images showed spherical and smooth surface shape of the PWP-based nanoparticles. DIM encapsulated by PWP showed enhanced stability at 4, 37 and 55°C for 15 days evidenced by changes in mean particle size and color (a*-value and b*-value) compared with control (DIM only). In conclusion, the polymerized whey protein based 3,3′-diindolylmethane nanoparticles are stable and the encapsulation may protect the core material from oxidation

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Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

HPLC of Formula: 1968-05-4. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 3,3′-Diindolylmethane, is researched, Molecular C17H14N2, CAS is 1968-05-4, about THE 3,3′-diindolylmethane promotes BDNF and antioxidant enzyme formation via TrkB/Akt pathway activation for neuroprotection against oxidative stress-induced apoptosis in hippocampal neuronal cells.

3,3′-Diindolylmethane (DIM), a metabolite of indole-3-carbinol present in Brassicaceae vegetables, possesses various health-promoting effects. Nonetheless, the effect of DIM on neurodegenerative diseases has not been elucidated clearly. In this study, we hypothesized DIM may protect neuronal cells against oxidative stress-induced apoptosis by promoting the formation of brain-derived neurotrophic factor (BDNF) and antioxidant enzymes through stabilizing the activation of the tropomyosin-related kinase receptor B (TrkB) cascade and we investigated the effect of DIM on oxidative stress-mediated neurodegenerative models. DIM protected neuronal cells against oxidative stress-induced apoptosis by regulating the expression of apoptosis-related proteins in glutamate-treated HT-22 cells. Addnl., DIM improved the expression of BDNF and antioxidant enzymes, such as heme oxygenase-1, glutamate-cysteine ligase catalytic subunit, and NAD(P)H quinine oxidoreductase-1, by promoting the activation of the TrkB/protein kinase B (Akt) pathway in the cells. Consistent with in vitro studies, DIM attenuated memory impairment by protecting hippocampal neuronal cells against oxidative damage in scopolamine-treated mice. Conclusionally, DIM exerted neuroprotective and antioxidant actions through the activation of both BDNF production and antioxidant enzyme formation in accordance with the TrkB/Akt pathway in neuronal cells. Such an effect of DIM may provide information for the application of DIM in the prevention of and therapy for neurodegenerative diseases.

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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Gut Microbes called Cruciferous vegetables (Brassica oleracea) confer cytoprotective effects in Drosophila intestines, Author is Lyles, James T.; Luo, Liping; Liu, Ken; Jones, Dean P.; Jones, Rheinallt M.; Quave, Cassandra L., which mentions a compound: 1968-05-4, SMILESS is C1(CC2=CNC3=C2C=CC=C3)=CNC4=C1C=CC=C4, Molecular C17H14N2, COA of Formula: C17H14N2.

Varieties and cultivars of the cruciferous vegetable Brassica oleracea are widely presumed to elicit pos. influences on mammalian health and disease, particularly related to their indole and sulforaphane content. However, there is a considerable gap in knowledge regarding the mechanisms whereby these plant-derived mols. elicit their beneficial effects on the host. In this study, we examined the chem. variation between B. oleracea varieties and evaluated their capacity to both activate Nrf2 in the Drosophila intestine and elicit cytoprotection. Ten types of edible B. oleracea were purchased and B. macrocarpa was wild collected. Fresh material was dried, extracted by double maceration and green kale was also subjected to anaerobic fermentation before processing. Untargeted metabolomics was used to perform Principal Component Anal. Targeted mass spectral anal. determined the presence of six indole species and quantified indole. Extracts were tested for their capacity to activate Nrf2 in the Drosophila intestine in third instar Drosophila larvae. Cytoprotective effects were evaluated using a paraquat-induced oxidative stress gut injury model. A “”Smurf”” assay was used to determine protective capacity against a chem. induced leaky gut. Extracts of Brussels sprouts and broccoli activated Nrf2 and protected against paraquat-induced damage and leaky gut. Lacto-fermented kale showed a cytoprotective effect, increasing survival by 20% over the non-fermented extract, but did not protect against leaky gut. The protective effects observed do not directly correlate with indole content, suggesting involvement of multiple compounds and a synergistic mechanism.

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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Liu, Xuelei; Ma, Shuang; Toy, Patrick H. published an article about the compound: 3,3′-Diindolylmethane( cas:1968-05-4,SMILESS:C1(CC2=CNC3=C2C=CC=C3)=CNC4=C1C=CC=C4 ).Name: 3,3′-Diindolylmethane. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1968-05-4) through the article.

The use of a halogen bond donor to catalyze Friedel-Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis(indolyl)methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these reactions proved to be more effective than a monondentate analog, a thiourea commonly used as an organocatalyst, and even a trityl cation that has been used previously in the synthesis of bis(indolyl)methanes.

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Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 1968-05-4, is researched, SMILESS is C1(CC2=CNC3=C2C=CC=C3)=CNC4=C1C=CC=C4, Molecular C17H14N2Journal, Article, Research Support, Non-U.S. Gov’t, Toxicology and Applied Pharmacology called AKT inhibitor AZD5363 suppresses stemness and promotes anti-cancer activity of 3,3′-diindolylmethane in human breast cancer cells, Author is Zhu, Kaiyuan; Liu, Xu; Liu, Chunxiao; Xu, Yuting; Fu, Yingqiang; Dong, Wei; Yan, Yadong; Wang, Wenjing; Qian, Cheng, the main research direction is diindolylmethane AKT human breast cancer cell anticancer activity; AKT inhibitor; CyTOF; Stemness.Electric Literature of C17H14N2.

The 3,3′-diindolylmethane (DIM) is a dimer compound converted from Indoly-3-carbinol that had been studied as promising chemo-preventive agent against breast cancer. In this study, we observed that proportion of CD133+Nanog+ subpopulation in MCF-7 cells was significantly increased after DIM administration with up-regulated AKT activity by using CyTOF assay. SPADE anal. revealed this stem-like subpopulation exhibited apoptosis-resistance property against DIM treatment. By combining with AKT inhibitor AZD5363, DIM induced CD133 expression could be suppressed. In addition, a combination treatment of MCF-7 and MDA-MB-231 breast cancer cells with DIM and AZD5363 showed synergistic decreases in cell proliferation and induced apoptosis. Furthermore, results from imaging flow cytometry suggested that FoxO3a nuclear localization and PUMA expression could be improved by combination of AZD5363 with DIM. Taken together, the above observations suggested that the combination of AZD5363 with DIM could be developed as potential therapy for breast cancer.

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SDS of cas: 1968-05-4. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 3,3′-Diindolylmethane, is researched, Molecular C17H14N2, CAS is 1968-05-4, about DIM mitigates the development of experimental autoimmune encephalomyelitis by maintaining the stability and suppressive function of regulatory T cells. Author is Yang, Sujuan; Tan, Lixi; Chen, Yingying; Liu, Aiqun; Hong, Mingfan; Peng, Zhongxing.

Recent studies have revealed that indoles, dietary ligands of the aryl hydrocarbon receptor (AhR), have immunomodulatory characteristics of balancing the differentiation of regulatory T cells (Tregs) and Th17 cells in multiple autoimmune diseases. In this study, we aimed to investigate the potency of the indole, 3,3′-diindolylmethane (DIM), on the stability and suppressive function of Tregs in exptl. autoimmune encephalomyelitis (EAE). Furthermore, we used the AhR antagonist CH223191 to verify that DIM exerts its effects on Tregs through the activation of AhR. We found that DIM treatment significantly alleviated the severity of EAE by maintaining the stability and suppressive function of Tregs instead of facilitating the differentiation of Tregs. Thus, these DIM-treated Tregs might indirectly inhibit the generation of Th17 cells and the production of proinflammatory cytokines. And we confirmed the critical role of AhR in the EAE model. Our study further investigated the mechanisms by which dietary indoles promote Treg activity in the EAE model. DIM may act as a novel therapeutic to restrain autoimmune inflammation in multiple sclerosis.

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