Synthesis and antibacterial evaluation of 3,3′-diindolylmethane derivatives

Roy, Sutapa Mondal; Gajbhiye, Rahul L.; Mandal, Mihirbaran; Pal, Churala; Meyyapan, Arumugam; Mukherjee, Joydeep; Jaisankar, Parasuraman

doi:10.1007/s00044-013-0737-7

Cited by 32 publications

(11 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A recent study indicated that DIM and synthesized DIM derivatives have antibacterial properties, including inhibition of S. aureus in vitro, at high concentrations (Roy et al, 2013). If DIM were to be effective in vivo to inhibit the bacteria, there could be a potential synergistic effect of DIM, acting on both the host immune response to SEB and the pathogen.…”

Section: Discussionmentioning

confidence: 99%

3,3'-Diindolylmethane Ameliorates Staphylococcal Enterotoxin B-Induced Acute Lung Injury through Alterations in the Expression of MicroRNA that Target Apoptosis and Cell-Cycle Arrest in Activated T Cells

Elliott

Nagarkatti

2016

Journal of Pharmacology and Experimental Therapeutics

View full text Add to dashboard Cite

3,39-Diindolylmethane (DIM), a natural indole found in cruciferous vegetables, has significant anti-cancer and anti-inflammatory properties. In this current study, we investigated the effects of DIM on acute lung injury (ALI) induced by exposure to staphylococcal enterotoxin B (SEB). We found that pretreatment of mice with DIM led to attenuation of SEB-induced inflammation in the lungs, vascular leak, and IFN-g secretion. Additionally, DIM could induce cell-cycle arrest and cell death in SEB-activated T cells in a concentration-dependent manner. Interestingly, microRNA (miRNA) microarray analysis uncovered an altered miRNA profile in lung-infiltrating mononuclear cells after DIM treatment of SEB-exposed mice. Moreover, computational analysis of miRNA gene targets and regulation networks indicated that DIM alters miRNA in the cell death and cell-cycle progression pathways. Specifically, DIM treatment significantly downregulated several miRNA and a correlative increase associated gene targets. Furthermore, overexpression and inhibition studies demonstrated that DIM-induced cell death, at least in part, used miR-222. Collectively, these studies demonstrate for the first time that DIM treatment attenuates SEB-induced ALI and may do so through the induction of microRNAs that promote apoptosis and cell-cycle arrest in SEB-activated T cells.

show abstract

Section: Discussionmentioning

confidence: 99%

3,3'-Diindolylmethane Ameliorates Staphylococcal Enterotoxin B-Induced Acute Lung Injury through Alterations in the Expression of MicroRNA that Target Apoptosis and Cell-Cycle Arrest in Activated T Cells

Elliott

Nagarkatti

2016

Journal of Pharmacology and Experimental Therapeutics

View full text Add to dashboard Cite

show abstract

“…For this reason, the mother liquors were combined and re-fractionated aiming at the intermediate characterization. Gratifyingly, the non-oxygenated oligomers 3,3'-diindolylmethane (DIM) [27] and 2-(indole-3-ylmethyl)-3,3'-diindolylmethane (LTr1) [28] were identified from the same I3C-exposed fungal culture. Accordingly, we were encouraged to propose that 1 and 3 were likely generated by expoxidizing DIM and LTr1, respectively (Scheme 1).…”

Section: Concise Reportmentioning

confidence: 99%

Bioactive Alkaloids from Indole‐3‐carbinol Exposed Culture of Daldiniaeschscholzii

Lin

Tan

2018

Chin. J. Chem.

View full text Add to dashboard Cite

Two new and rare bioactive indoles named dalesindoloids A (1) and B (3), along with 3‐(1H‐indole‐3ylmethyl)‐2‐oxindole (2), were characterized from the indole‐3‐carbinol (I3C)‐exposed culture of Daldinia eschscholzii. The absolute configuration of 2 was determined by quantum chemical calculations of the electronic circular dichroism (ECD) spectrum. Dalesindoloids A and B were cytotoxic against the leukemia HL‐60 cell line with the IC50 values of 1.0 and 7.4 μmol/L, respectively, with the former being inhibitory on Staphylococcus aureus (MIC: 9.1 μmol/L). The simultaneous characterization of the alkaloids from the I3C‐exposed fungal culture highlighted that the 2,3‐epoxyindoline motif can be transformed into both lactam and indolin‐3‐one moieties. This is the first‐time description of the 2,3‐epoxyindoline chemical versatility and Wagner‐Meerwein rearrangement (WMR) reaction in the microbial culture.

show abstract

“…DIM has potential ability to prevent different types of cancer [ 4 , 5 ], especially human breast cancer [ 6 ]. DIM has a promising effect to treat thyroid proliferative disease by promoting healthier estrogen metabolism [ 7 ] and can be used as an antibacterial [ 8 ]. However, the stability of DIM is a major challenge for its practical applications.…”

Section: Introductionmentioning

confidence: 99%

Physicochemical and Microstructural Properties of Polymerized Whey Protein Encapsulated 3,3′-Diindolylmethane Nanoparticles

et al. 2019

View full text Add to dashboard Cite

The fat-soluble antioxidant 3,3′-diindolylmethane (DIM), is a natural phytochemical 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, rheological 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 negative (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 Infrared (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.

show abstract

Synthesis and antibacterial evaluation of 3,3′-diindolylmethane derivatives

Cited by 32 publications

References 16 publications

3,3'-Diindolylmethane Ameliorates Staphylococcal Enterotoxin B-Induced Acute Lung Injury through Alterations in the Expression of MicroRNA that Target Apoptosis and Cell-Cycle Arrest in Activated T Cells

3,3'-Diindolylmethane Ameliorates Staphylococcal Enterotoxin B-Induced Acute Lung Injury through Alterations in the Expression of MicroRNA that Target Apoptosis and Cell-Cycle Arrest in Activated T Cells

Bioactive Alkaloids from Indole‐3‐carbinol Exposed Culture of Daldiniaeschscholzii

Physicochemical and Microstructural Properties of Polymerized Whey Protein Encapsulated 3,3′-Diindolylmethane Nanoparticles

Contact Info

Product

Resources

About