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STAR Protocols Dec 2022Aromatic azo dyes bear immense commercial significance because of their extensive usage in the textile, paint, and food industries. With growing environmental concerns,...
Aromatic azo dyes bear immense commercial significance because of their extensive usage in the textile, paint, and food industries. With growing environmental concerns, developing alternative greener approaches for the synthesis of azo dyes is crucial. Herein, we describe a metal-free, microwave (MW)-assisted protocol for rapid access to a large variety of unsymmetrical azo dyes by coupling nitroarenes and aromatic amines. After MW-assisted coupling, the azo dyes are then isolated by precipitation followed by recrystallization to obtain pure azo dyes. For complete details on the use and execution of this protocol, please refer to Thakuri et al. (2022)..
Topics: Azo Compounds; Microwaves; Textiles; Amines
PubMed: 36595940
DOI: 10.1016/j.xpro.2022.101864 -
Frontiers in Bioscience (Elite Edition) Jan 2012Approximately 0.7 million tons of azo dyes are synthesized each year. Azo dyes are composed of one or more R₁-N=N-R₂ linkages. Studies have shown that both mammalian... (Review)
Review
Approximately 0.7 million tons of azo dyes are synthesized each year. Azo dyes are composed of one or more R₁-N=N-R₂ linkages. Studies have shown that both mammalian and microbial azoreductases cleave the azo bonds of the dyes to form compounds that are potentially genotoxic. The human gastrointestinal tract harbors a diverse microbiota comprised of at least several thousand species. Both water-soluble and water-insoluble azo dyes can be reduced by intestinal bacteria. Some of the metabolites produced by intestinal microbiota have been shown to be carcinogenic to humans although the parent azo dyes may not be classified as being carcinogenic. Azoreductase activity is commonly found in intestinal bacteria. Three types of azoreductases have been characterized in bacteria. They are flavin dependent NADH preferred azoreductase, flavin dependent NADPH preferred azoreductase, and flavin free NADPH preferred azoreductase. This review highlights how azo dyes are metabolized by intestinal bacteria, mechanisms of azo reduction, and the potential contribution in the carcinogenesis/mutagenesis of the reduction of the azo dyes by intestinal microbiota.
Topics: Azo Compounds; Bacteria; Carcinogens; Coloring Agents; Humans; Intestines
PubMed: 22201895
DOI: 10.2741/e400 -
International Journal of Molecular... Mar 2021The high biological activity of the chromene compounds coupled with the intriguing optical features of azo chromophores prompted our desire to construct novel...
The high biological activity of the chromene compounds coupled with the intriguing optical features of azo chromophores prompted our desire to construct novel derivatives of chromene incorporating azo moieties 4a-l, which have been prepared via a three-component reaction of 1-naphthalenol-4-[(4-ethoxyphenyl) azo], 1, with the benzaldehyde derivatives and malononitrile. The structural identities of the azo-chromene 4a-l were confirmed on the basis of their spectral data and elemental analysis, and a UV-visible study was performed in a Dimethylformamide (DMF) solution for these molecules. Additionally, the antimicrobial activity was investigated against four human pathogens (Gram-positive and Gram-negative bacteria) and four fungi, employing an agar well diffusion method, with their minimum inhibitory concentrations being reported. Molecules 4a, 4g, and 4h were discovered to be more efficacious against (RCMB 05922) in comparison to the reference drugs, while compounds 4b and 4h demonstrated the highest inhibitory activity against () in evaluation against the reference drugs. Moreover, their cytotoxicity was assessed against three different human cell lines, including human colon carcinoma (HCT-116), human hepatocellular carcinoma (HepG-2), and human breast adenocarcinoma (MCF-7) with a selection of molecules illustrating potency against the HCT-116 and MCF-7 cell lines. Furthermore, the molecular modeling results depicted the binding interactions of the synthesized compounds 3b and 3h in the active site of the DNA gyrase B enzyme with a clear SAR (structure-activity relationship) analysis. Lastly, the density functional theory's (DFTs) theoretical calculations were performed to quantify the energy levels of the Frontier Molecular Orbitals (FMOs) and their energy gaps, dipole moments, and molecular electrostatic potentials. These data were utilized in the chemical descriptor estimations to confirm the biological activity.
Topics: Anti-Infective Agents; Antineoplastic Agents; Azo Compounds; Benzopyrans; Cell Proliferation; Computer Simulation; Escherichia coli; HCT116 Cells; Hep G2 Cells; Humans; MCF-7 Cells; Mucorales; Neoplasms
PubMed: 33802075
DOI: 10.3390/ijms22062807 -
International Journal of Nanomedicine 2019Aiming to produce pyridine azo disperse dyes with good fastness properties and promising antimicrobial activity, a number of novel systems of polyfunctionalized pyridine...
AIM
Aiming to produce pyridine azo disperse dyes with good fastness properties and promising antimicrobial activity, a number of novel systems of polyfunctionalized pyridine azo dyes and their selenium nanoparticles (SeNPs) were synthesized.
MATERIALS AND METHODS
The synthesized products were formed by the reaction of diazotized aniline derivatives or diazotized amino antipyrene with any of dibenzoyl methane or benzoyl acetone and cyanoacetamide in boiling ethanolic sodium ethoxide. The structures of the newly synthesized compounds were elucidated by elemental analysis and spectral data. Moreover, (SeNPs) of the pyridine azo disperse dyes were characterized by Ultra-Violet -Visible spectrophotometry, dynamic light scattering , X-ray diffraction, and transmission electron microscope analysis. On the other hand, the synthesized dyes and its (SeNPs) were applied for disperse dyeing of nylon 66 and their fastness properties were measured, such as washing, rubbing, perspiration, and light fastness. In addition, the antimicrobial activities for all the synthesized compounds and for (SeNPs) prepared compounds () were evaluated.
RESULTS
Compounds , and were the most active compounds against all Gram-positive and Gram-negative bacterial species. While, compounds , and were the most active toward some of the bacterial strains (at least two from the selected four strains). Moreover, compounds showed higher activity toward the fungal strain. Also, the minimal inhibitory concentrations for all the most active compounds were determined.
CONCLUSION
Finally, all the (SeNPs) compounds revealed higher activity against bacterial and fungal strains than the other synthesized compounds.
Topics: Anti-Bacterial Agents; Azo Compounds; Bacteria; Fungi; Metal Nanoparticles; Microbial Sensitivity Tests; Pyridines; Selenium; X-Ray Diffraction
PubMed: 31632007
DOI: 10.2147/IJN.S216914 -
International Journal of Molecular... Jan 2022Fluorescent molecular assembly systems provide an exciting platform for creating stimuli-responsive nano- and microstructured materials with optical, electronic, and...
Fluorescent molecular assembly systems provide an exciting platform for creating stimuli-responsive nano- and microstructured materials with optical, electronic, and sensing functions. To understand the relationship between (i) the plausible molecular structures preferentially adopted depending on the solvent polarity (such as N,N-dimethylformamide [DMF], tetrahydrofuran [THF], and toluene), (ii) the resulting spectroscopic features, and (iii) self-assembled nano-, micro-, and macrostructures, we chose a sterically crowded triangular azo dye (3Bu) composed of a polar molecular core and three peripheral biphenyl wings. The chromophore changed the solution color from yellow to pink-red depending on the solvent polarity. In a yellow DMF solution, a considerable amount of the twisted azo form could be kept stable with the help of favorable intermolecular interactions with the solvent molecules. By varying the concentration of the DMF solution, the morphology of self-assembled structures was transformed from nanoparticles to micrometer-sized one-dimensional (1D) structures such as sticks and fibers. In a pink-red toluene solution, the periphery of the central ring became more planar. The resulting significant amount of the keto-hydrazone tautomer grew into micro- and millimeter-sized 1D structures. Interestingly, when THF-HO (1:1) mixtures were stored at a low temperature, elongated fibers were stacked sideways and eventually developed into anisotropic two-dimensional (2D) sheets. Notably, subsequent exposure of visible-light-irradiated sphere samples to solvent vapor resulted in reversible fluorescence off↔on switching accompanied by morphological restoration. These findings suggest that rational selection of organic dyes, solvents, and light is important for developing reusable fluorescent materials.
Topics: Azo Compounds; Coloring Agents; Crystallography, X-Ray; Light; Models, Molecular; Molecular Structure; Nanostructures; Solvents
PubMed: 35055154
DOI: 10.3390/ijms23020965 -
Molecules (Basel, Switzerland) Dec 2022Two groups of laterally substituted non-mesomorphic and liquid crystalline materials bearing monoazo group were prepared and investigated via experimental and...
Two groups of laterally substituted non-mesomorphic and liquid crystalline materials bearing monoazo group were prepared and investigated via experimental and theoretical techniques. The molecular structures of the designed dyes were evaluated by FT-IR and NMR spectroscopic analyses. Mesomorphic examinations for all synthesized dyes were investigated by polarized optical microscopy (POM) and differential scanning calorimetry (DSC). Results revealed that, the thermal and optical properties of investigated compounds are mainly dependent on their molecular geometry. The optimized geometries of the azo derivatives and their electronic absorption of the dyes were carried out using the B3LYP/6-311G level of the DFT method. The azo dyes were measured for their dyeing performance on polyester fabrics. The dyed fabrics have excellent fastness properties with a color strength of 1.49-3.43 and an exhaustion rate of 82-64%. The chemical descriptor parameters of disperse azo dyes in gas phase were calculated and correlated with dyeing parameters.
Topics: Coloring Agents; Spectroscopy, Fourier Transform Infrared; Azo Compounds; Polyesters; Textiles
PubMed: 36558116
DOI: 10.3390/molecules27248980 -
Cell Chemical Biology Nov 2021Despite the power of photopharmacology for interrogating signaling proteins, many photopharmacological systems are limited by their efficiency, speed, or spectral...
Despite the power of photopharmacology for interrogating signaling proteins, many photopharmacological systems are limited by their efficiency, speed, or spectral properties. Here, we screen a library of azobenzene photoswitches and identify a urea-substituted "azobenzene-400" core that offers bistable switching between cis and trans with improved kinetics, light sensitivity, and a red-shift. We then focus on the metabotropic glutamate receptors (mGluRs), neuromodulatory receptors that are major pharmacological targets. Synthesis of "BGAG," a photoswitchable orthogonal, remotely tethered ligand (PORTL), enables highly efficient, rapid optical agonism following conjugation to SNAP-tagged mGluR2 and permits robust optical control of mGluR1 and mGluR5 signaling. We then produce fluorophore-conjugated branched PORTLs to enable dual imaging and manipulation of mGluRs and highlight their power in ex vivo slice and in vivo behavioral experiments in the mouse prefrontal cortex. Finally, we demonstrate the generalizability of our strategy by developing an improved soluble, photoswitchable pore blocker for potassium channels.
Topics: Animals; Azo Compounds; Cells, Cultured; Female; Humans; Ligands; Mice; Photochemical Processes; Potassium Channels; Receptors, Metabotropic Glutamate; Signal Transduction
PubMed: 33735619
DOI: 10.1016/j.chembiol.2021.02.020 -
Organic & Biomolecular Chemistry Apr 2019This review describes catalytic asymmetric cycloaddition reactions of silyl-protected enoldiazo compounds for the construction of highly functionalized carbo- and... (Review)
Review
This review describes catalytic asymmetric cycloaddition reactions of silyl-protected enoldiazo compounds for the construction of highly functionalized carbo- and heterocycles which possess one or more chiral center(s). The enoldiazo compound or its derivative, donor-acceptor cyclopropene, form electrophilic vinylogous metal carbene intermediates that combine stepwise with nucleophilic dipolar reactants to form products from [3 + 1]-, [3 + 2]-, [3 + 3]-, [3 + 4]-, and [3 + 5]-cycloaddition, generally in high yield and with exceptional stereocontrol and regioselectivity.
Topics: Azo Compounds; Catalysis; Copper; Cycloaddition Reaction; Molecular Structure; Stereoisomerism
PubMed: 30924829
DOI: 10.1039/c9ob00478e -
F1000Research 2020Azo compounds, containing naphthol and diazonium salts, are synthetic dyes widely used in the batik industry. Azo compounds are considered toxic when they are exposed...
Azo compounds, containing naphthol and diazonium salts, are synthetic dyes widely used in the batik industry. Azo compounds are considered toxic when they are exposed to human tissue. The purpose of this study was to analyze buccal cell DNA exposed to azo compounds in batik workers. A cross-sectional study involving 20 male subjects divided into two groups (n=10 group), namely azo-exposed and non-exposed (control group). Inclusion criteria were batik workers of the colouring division who have been exposed to azo for at least 5 years. Buccal cells were taken using cytobrush then DNA were isolated from buccal cell. DNA isolation was done by buccal DNA kit, while the purity and concentration of the DNA was determined using spectrophotometer and electrophoresis. The azo-exposed group revealed higher purity DNA than those in the control group. The purity of the DNA in the azo-exposed group and control group was 0.61±0.93 and 0.21±0.09, respectively, while the concentration of DNA was of 59.02 and 19.35 ng/UL, respectively. The ratio at 260/280 nm was 1.84-1.94 (azo-exposed) and 1.85-1.92 (control). Principal component analysis using the first principle component (PC1) and second principle component (PC2) could successfully classify subjects in the control and azo-exposed groups. Characteristics of DNA could be used as an indication of exposure to azo compounds in workers of batik industries.
Topics: Azo Compounds; Coloring Agents; Cross-Sectional Studies; DNA; Humans; Male; Mouth Mucosa
PubMed: 33014347
DOI: 10.12688/f1000research.25798.2 -
Ecotoxicology and Environmental Safety Sep 2023The presence of high salinity levels in textile wastewater poses a significant obstacle to the process of decolorizing azo dyes. The present study involved the...
The presence of high salinity levels in textile wastewater poses a significant obstacle to the process of decolorizing azo dyes. The present study involved the construction of a yeast consortium HYC, which is halotolerant and was recently isolated from wood-feeding termites. The consortium HYC was mainly comprised of Sterigmatomyces halophilus SSA-1575 and Meyerozyma guilliermondii SSA-1547. The developed consortium demonstrated a decolourization efficiency of 96.1% when exposed to a concentration of 50 mg/l of Reactive Black 5 (RB5). The HYC consortium significantly decolorized RB5 up to concentrations of 400 mg/l and in the presence of NaCl up to 50 g/l. The effects of physicochemical factors and the degradation pathway were systematically investigated. The optimal pH, salinity, temperature, and initial dye concentration were 7.0, 3%, 35 °C and 50 mg/l, respectively. The co-carbon source was found to be essential, and the addition of glucose resulted in a 93% decolorization of 50 mg/l RB5. The enzymatic activity of various oxido-reductases was assessed, revealing that NADH-DCIP reductase and azo reductase exhibited greater activity in comparison to other enzymes. UV-Visible (UV-vis) spectrophotometry, Fourier-transform infrared spectroscopy (FTIR), high-performance liquid chromatography (HPLC), and gas chromatography-mass spectrometry (GC-MS) were utilized to identify the metabolites generated during the degradation of RB5. Subsequently, a metabolic pathway was proposed. The confirmation of degradation was established through alterations in the functional groups and modifications in molecular weight. The findings indicate that this halotolerant yeast consortium exhibits promising potential of degrading dye compounds. The results of this study offer significant theoretical basis and crucial perspectives for the implementation of halotolerant yeast consortia in the bioremediation of textile and hypersaline wastewater. This approach is particularly noteworthy as it does not produce aromatic amines.
Topics: Azo Compounds; Wastewater; Gas Chromatography-Mass Spectrometry; Chromatography, High Pressure Liquid; Biodegradation, Environmental; Coloring Agents
PubMed: 37478569
DOI: 10.1016/j.ecoenv.2023.115258