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Chemosphere Feb 2023No biodegradation methods are absolute in the treatment of all textile dyes, which leads to structure-dependent degradation. In this study, biodegradation of three azo...
Understanding the biodegradation pathways of azo dyes by immobilized white-rot fungus, Trametes hirsuta D7, using UPLC-PDA-FTICR MS supported by in silico simulations and toxicity assessment.
No biodegradation methods are absolute in the treatment of all textile dyes, which leads to structure-dependent degradation. In this study, biodegradation of three azo dyes, reactive black 5 (RB5), acid blue 113 (AB113), and acid orange 7 (AO7), was investigated using an immobilized fungus, Trametes hirsuta D7. The degraded metabolites were identified using UPLC-PDA-FTICR MS and the biodegradation pathway followed was proposed. RB5 (92%) and AB113 (97%) were effectively degraded, whereas only 30% of AO7 was degraded. Molecular docking simulations were performed to determine the reason behind the poor degradation of AO7. Weak binding affinity, deficiency in H-bonding interactions, and the absence of interactions between the azo (-NN-) group and active residues of the model laccase enzyme were responsible for the low degradation efficiency of AO7. Furthermore, cytotoxicity and genotoxicity assays confirmed that the fungus-treated dye produced non-toxic metabolites. The observations of this study will be useful for understanding and further improving enzymatic dye biodegradation.
Topics: Trametes; Molecular Docking Simulation; Biodegradation, Environmental; Azo Compounds; Coloring Agents; Laccase
PubMed: 36509189
DOI: 10.1016/j.chemosphere.2022.137505 -
The American Journal of Medicine Sep 1989
Topics: Attitude to Health; Azo Compounds; Drama; History, 20th Century; Literature; Literature, Modern; Medicine in Literature; United Kingdom; p-Aminoazobenzene
PubMed: 2672813
DOI: 10.1016/s0002-9343(89)80184-6 -
British Medical Journal (Clinical... Jan 1983
Topics: Azo Compounds; Drug Hypersensitivity; Food Hypersensitivity; Humans; Tartrazine
PubMed: 6401501
DOI: No ID Found -
Brazilian Journal of Biology = Revista... 2023Amazonian strains of Cyathus spp. and Geastrum spp. were studied for the ability to discolor the trypan blue azo dye and reduce its toxicity. Discoloration of trypan...
Amazonian strains of Cyathus spp. and Geastrum spp. were studied for the ability to discolor the trypan blue azo dye and reduce its toxicity. Discoloration of trypan blue dye (0.05%) was evaluated in solid and aqueous medium over different periods. The reduction of dye toxicity after treatment was assessed by seed germination and the development of lettuce seedlings (Lactuca sativa L.) and toxicity test in Artemia salina (L.) larvae. All evaluated strains showed the potential to reduce the color intensity of trypan blue dye. Cyathus strains reached 96% discoloration, and C. albinus and C. limbatus also reduced dye toxicity. Geastrum strains showed a high efficiency degree in color reduction, reaching 98% discoloration, however, the by-products generated during the process presented toxicity and require further investigation. For the first time, Amazonian strains of gasteroid fungi degrading trypan blue are reported, some even reducing its toxicity. Thus, making them promising sources of enzymes of interest to bioremediation scenarios involving synthetic dyes.
Topics: Trypan Blue; Azo Compounds; Biodegradation, Environmental; Basidiomycota; Fungi; Coloring Agents
PubMed: 38055583
DOI: 10.1590/1519-6984.277577 -
Chemical Reviews Apr 2002
Review
Topics: Azo Compounds; Nitric Oxide; Nitric Oxide Donors; Oxygen; Terminology as Topic
PubMed: 11942789
DOI: 10.1021/cr000028t -
Spectrochimica Acta. Part A, Molecular... May 2014Nine new bis-azo dyes derived from 5-arylidene-2,4-thiazolidinone have been synthesized in two steps using Knoevenagel condensation and diazotization-coupling reaction....
Nine new bis-azo dyes derived from 5-arylidene-2,4-thiazolidinone have been synthesized in two steps using Knoevenagel condensation and diazotization-coupling reaction. The structures of the compounds were confirmed by UV-vis, IR, (1)H NMR and (13)C NMR spectroscopic techniques. The spectral characterizations demonstrate that there is an equilibrium between the azo (T1) and hydrazine (T2 and T3) tautomers for all prepared dyes in solutions. In addition, the solvatochromic behavior of the prepared dyes was evaluated using polarity/polarizability parameter (π(*)) in various solvents. The UV-vis absorption spectra of dyes show a bathochromic shift with increasing polarity and base strength of the solvents. Finally, the effects of acid and base on the UV-vis absorption spectra of the dyes with different substituent in diazo component are reported.
Topics: Azo Compounds; Coloring Agents; Magnetic Resonance Spectroscopy; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared; Stereoisomerism; Thiazolidines
PubMed: 24594883
DOI: 10.1016/j.saa.2014.02.010 -
Applied Microbiology and Biotechnology Sep 2013Geobacter metallireducens was found to be capable of decolorizing several azo dyes with different structures to various extents. Pyruvate, ethanol, acetate, propionate,...
Geobacter metallireducens was found to be capable of decolorizing several azo dyes with different structures to various extents. Pyruvate, ethanol, acetate, propionate, and benzoate could support 66.3 ± 2.6-93.7 ± 2.1 % decolorization of 0.1 mM acid red 27 (AR27) in 40 h. The dependence of the specific decolorization rate on AR27 concentration (25 to 800 μM) followed Michaelis-Menten kinetics (K m = 186.9 ± 1.4 μΜ, V max = 0.65 ± 0.02 μmol mg protein(-1) h(-1)). Enhanced AR27 decolorization was observed with the increase of cell concentrations ranging from 7.5 to 45 mgL(-1). AR27 decolorization by G. metallireducens was retarded by the presence of goethite, which competed electrons with AR27 and was reduced to Fe(II). The addition of low concentrations of humic acid (1-100 mgL(-1)) or 2-hydroxy-1,4-naphthoquinone (0.5-50 μM) could improve the decolorization performance of G. metallireducens. High-performance liquid chromatography analysis suggested reductive pathway to be responsible for decolorization. This was the first study on azo dye decolorization by Geobacter strain and might improve our understanding of natural attenuation and bioremediation of environments polluted by azo dyes.
Topics: Azo Compounds; Biodegradation, Environmental; Coloring Agents; Geobacter; Kinetics
PubMed: 23132348
DOI: 10.1007/s00253-012-4545-7 -
Annual Review of Pharmacology and... 2003Diazeniumdiolates, compounds of structure R(1)R(2)NN(O)=NOR(3), which have also been called NONOates, have proven useful for treating an increasing diversity of medical... (Review)
Review
Diazeniumdiolates, compounds of structure R(1)R(2)NN(O)=NOR(3), which have also been called NONOates, have proven useful for treating an increasing diversity of medical disorders in relevant animal models. Here, I review the chemical features that make them such excellent starting points for designing materials capable of targeting reliable and controllable fluxes of bioactive NO for in vitro and in vivo applications. This is followed by a consideration of recent proof-of-concept studies that underscore what I believe to be the substantial clinical promise of such materials. Examples covered include progress toward inhibiting restenosis after angioplasty, preparing thromboresistant medical devices, reversing vasospasm, and relieving pulmonary hypertension. Together with a very recent report describing the beneficial effects of diazeniumdiolate therapy in a patient with acute respiratory distress syndrome, the results of the animal experiments support the prediction that a broad selection of problems in clinical medicine can be solved by judiciously mining the enormous variety of possible R(1)R(2)NN(O)=NOR(3) structures.
Topics: Azo Compounds; Drug Design; Humans; Nitric Oxide; Nitric Oxide Donors; Structure-Activity Relationship
PubMed: 12415121
DOI: 10.1146/annurev.pharmtox.43.100901.135831 -
Chemphyschem : a European Journal of... Jun 2005A systematic study of the degenerate two-photon absorption (2PA) spectra of seven azoaromatic compounds in dimethyl sulfoxide solution is reported, which employed the...
A systematic study of the degenerate two-photon absorption (2PA) spectra of seven azoaromatic compounds in dimethyl sulfoxide solution is reported, which employed the Z-scan technique with femtosecond laser pulses from the bottom of the azo compound absorption bands up to 1100 nm. The 2PA peaks for pseudostilbene-type azo compounds (Disperse Orange (DO) 3, Disperse Red (DR) 13, DR1, DR19, and DR19-Cl) were observed at twice the peak wavelength of the linear absorption. However, such peaks were not observed for other azo compounds (PAMINO and DIAMINO) because of the symmetry of these molecules. A resonance enhancement of the 2PA cross-section was observed for all compounds. The 2PA peak and the nonlinear resonance enhancement behavior could be adjusted with a model based on perturbation theory. Such knowledge can be a guideline to the understanding of the 2PA process in azoaromatic compounds.
Topics: Azo Compounds; Photons
PubMed: 15887191
DOI: 10.1002/cphc.200400391 -
Dermatitis : Contact, Atopic,...
Topics: Azo Compounds; Coloring Agents; Dermatitis, Allergic Contact; Humans; Solid Phase Extraction; Solvents; Textiles
PubMed: 33273218
DOI: 10.1097/DER.0000000000000652