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Food and Chemical Toxicology : An... Oct 2021Azo-dyes such as Allura Red, Carmoisine, Amaranth, Sunset Yellow (SY), Brilliant Blue, Tartrazine (Tz), etc., are popular as food coloring agents due to their low cost... (Review)
Review
Azo-dyes such as Allura Red, Carmoisine, Amaranth, Sunset Yellow (SY), Brilliant Blue, Tartrazine (Tz), etc., are popular as food coloring agents due to their low cost and stability. SY and Tz are the most used members of this group of dyes since they have similar colors and are usually used together in food products. Despite their advantageous industrial use, they exhibit a risk toxicity profile with adverse effects such as allergy, asthma, carcinogenicity, genotoxicity, cytotoxicity, anxiety, etc. Therefore, the United States Food and Drug Administration (FDA) and European Food Safety Authority (EFSA) regulate the permissions for using these compounds to provide safe food products for consumers and prevent adverse effects both short and long-term. Considering all of these, for the analysis of azo toxic dyes, highly sensitive, low-cost, simple, and rapid sensors are necessary. Electrochemical nanosensors, which combine the unique features of electrochemistry and nanotechnology, are devices with all these advantages and are widely used for the determination of azo dyes. SY and Tz step forth as the most used food dyes in the class of azo-toxic dyes. They are often preferred together in food products, increasing the occurrence and exposure risk. Therefore, the analysis of Sunset Yellow and Tartrazine in food products has significant importance. In this review, the latest nanomaterial-based approaches for the electrochemical sensors on the analysis of SY and Tz in food samples were evaluated in terms of used nanomaterials and applied food samples.
Topics: Azo Compounds; Electrochemical Techniques; Food Analysis; Food Contamination; Tartrazine
PubMed: 34454997
DOI: 10.1016/j.fct.2021.112524 -
Chemosphere Jul 2016Azo dyes account for >70% of the global industrial demand (∼9 million tons). Owing to their genotoxic/carcinogenic potential, the annual disposal of ∼4,500,000 tons... (Review)
Review
Azo dyes account for >70% of the global industrial demand (∼9 million tons). Owing to their genotoxic/carcinogenic potential, the annual disposal of ∼4,500,000 tons of dyes and/or degraded products is an environmental and socio-economic concern. In comparison to physico-chemical methods, microbe-mediated dye degradation is considered to be low-input, cost-effective and environmentally-safe. However, under different environmental conditions, interactions of chemically diverse dyes with metabolically diverse microbes produce metabolites of varying toxicity. In addition, majority of studies on microbial dye-degradation focus on decolorization with least attention towards detoxification. Therefore, the environmental significance of microbial dye detoxification research of past >3 decades is critically evaluated with reference to dye structure and the possible influence of microbial interactions in different environments. In the absence of ecosystem-based studies, the results of laboratory-based studies on dye degradation, metabolite production and their genotoxic impact on model organisms are used to predict the possible fate and consequences of azo dyes/metabolites in the environment. In such studies, the predominance of fewer numbers of toxicological assays that too at lower levels of biological organization (molecular/cellular/organismic) suggests its limited ecological significance. Based on critical evaluation of these studies the recommendations on inclusion of multilevel approach (assessment at multiple levels of biological organization), multispecies microcosm approach and native species approach in conjunction with identification of dye metabolites have been made for future studies. Such studies will bridge the gap between the fundamental knowledge on dye-microbe-environment interactions and its application to combat dye-induced environmental toxicity. Thus an environmental perspective on dye toxicity in the background of dye structure and effects of environmental processes has been developed. Based on past 3 decades of research on microbial dye detoxification, the current state of knowledge has been analyzed, environmental relevance of these studies was ascertained, research gaps in microbe-mediated azo dye detoxification have been identified and a research framework emphasizing a better understanding of complex interactions between dye-microbe and environmental processes has been proposed. It provides directions for undertaking environmentally sound microbial dye detoxification research.
Topics: Azo Compounds; Bacteria; Biodegradation, Environmental; Coloring Agents; Environmental Pollutants; Humans
PubMed: 27155475
DOI: 10.1016/j.chemosphere.2016.04.068 -
Discovery of a novel photoswitchable PI3K inhibitor toward optically-controlled anticancer activity.Bioorganic & Medicinal Chemistry Oct 2022Light has been used increasingly as an external stimulus in drug design. Herein, we report a novel photoswitchable azo-PI3K inhibitor, which bears an azobenzene moiety...
Light has been used increasingly as an external stimulus in drug design. Herein, we report a novel photoswitchable azo-PI3K inhibitor, which bears an azobenzene moiety and can be efficiently converted between trans and cis configuration with changes of anticancer activity upon different light irradiation. Its photochemical properties were characterized by UV, LC-MS and NMR techniques. In biological assessment, trans and cis isomers of the azo-PI3K inhibitor exhibited differential anticancer activity in inhibition of PI3K pathway, cell migratory ability, and colony formation and can be switched at a cellular level upon light irradiation. Moreover, both isomers of the azo-PI3K inhibitor significantly inhibited tumor growth in a zebrafish xenograft model. Together, this photoswitchable azo-PI3K inhibitor may be useful as a valuable tool compound for studying the PI3K pathway and further optimization toward optically-controlled anticancer activity.
Topics: Animals; Azo Compounds; Humans; Isomerism; Phosphatidylinositol 3-Kinases; Phosphoinositide-3 Kinase Inhibitors; Photochemical Processes; Zebrafish
PubMed: 36049360
DOI: 10.1016/j.bmc.2022.116975 -
Bioresource Technology May 2022This study presents an eco-friendly and efficient technology, using immobilized enzymes, vault-encapsulated laccases (vlaccase), for decolorization and detoxification of...
This study presents an eco-friendly and efficient technology, using immobilized enzymes, vault-encapsulated laccases (vlaccase), for decolorization and detoxification of dyes. Vault encapsulation remarkably improved the performance of laccase at industrially relevant conditions, including neutral to alkaline pH and relatively high temperatures. Two representative anthraquinone and azo dyes, Reactive Blue 19 and Acid Orange 7, respectively, were rapidly decolorized (72% and 80%) by vlaccase treatment while natural laccase (nlaccase) achieved 40% and 32% decolorization. The toxicity of treated and untreated dyes was tested on model bacterial, algal, and insect cells. The inhibitory effects of dyes towards selected bacteria were reduced in vlaccase-treated samples. The chlorophyll synthesis in algae was less inhibited by dyes after vlaccase treatment. Furthermore, the toxicity of dye degradation products to insect cells was significantly mitigated in the vlaccase group. Collectively, these results indicate that vlaccase is a stable and strong enzymatic system for removing dyes from waters.
Topics: Azo Compounds; Biodegradation, Environmental; Coloring Agents; Enzymes, Immobilized; Laccase; Nanoparticles
PubMed: 35318145
DOI: 10.1016/j.biortech.2022.127040 -
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 -
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 -
Macromolecular Rapid Communications Jan 2018Metal-organic frameworks (MOFs) are nanoporous, crystalline hybrid materials, which enable various functionalities by incorporating functional organic molecules. By... (Review)
Review
Metal-organic frameworks (MOFs) are nanoporous, crystalline hybrid materials, which enable various functionalities by incorporating functional organic molecules. By using organic linker molecules that possess photoswitchable azobenzene side groups, the remote control over certain properties was introduced to MOFs. Different MOF materials in the form of powders and thin films have been used to demonstrate the photoswitching. The applications of these stimuli-responsive nanoporous solids range from switching the adsorption capacity of various gases over remote-controlled release of guest molecules to continuously tunable membrane separation of molecular mixtures. A particular focus of this review is the effect of the azobenzene photoswitching on the host-guest interaction, enabling smart applications of the material. Steric hindrance, which may suppress the photoswitching in some MOF structures, is also discussed.
Topics: Azo Compounds; Metal-Organic Frameworks; Molecular Structure; Photochemical Processes
PubMed: 28758288
DOI: 10.1002/marc.201700239 -
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 -
Journal of Materials Chemistry. B Oct 2020Dynamic biochemical and biophysical signals of cellular matrix define and regulate tissue-specific cell functions and fate. To recapitulate this complex environment in... (Review)
Review
Dynamic biochemical and biophysical signals of cellular matrix define and regulate tissue-specific cell functions and fate. To recapitulate this complex environment in vitro, biomaterials based on structural- or degradation-tunable polymers have emerged as powerful platforms for regulating the "on-demand" cell-material dynamic interplay. As one of the most prevalent photoswitch molecules, the photoisomerization of azobenzene demonstrates a unique advantage in the construction of dynamic substrates. Moreover, the development of azobenzene-containing biomaterials is particularly helpful in elucidating cells that adapt to a dynamic microenvironment or integrate spatiotemporal variations of signals. Herein, this minireview, places emphasis on the research progress of azobenzene photoswitches in the dynamic regulation of matrix signals. Some techniques and material design methods have been discussed to provide some theoretical guidance for the rational and efficient design of azopolymer-based material platforms. In addition, considering that the UV-light response of traditional azobenzene photoswitches is not conducive to biological applications, we have summarized the recent approaches to red-shifting the light wavelength for azobenzene activation.
Topics: Animals; Azo Compounds; Cell Line, Tumor; Cellular Microenvironment; Coated Materials, Biocompatible; Electric Conductivity; Extracellular Matrix; Humans; Isomerism; Light; Polymers; Surface Properties
PubMed: 32929441
DOI: 10.1039/d0tb01737j