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Bioconjugate Chemistry Jan 2018Hyperbranched polyamidoamines (h-PAMAM) were prepared using a one-pot reaction to have similar molecular weight to third generation PAMAM (G3-PAMAM) dendrimers, and then...
Hyperbranched polyamidoamines (h-PAMAM) were prepared using a one-pot reaction to have similar molecular weight to third generation PAMAM (G3-PAMAM) dendrimers, and then functionalized with N-diazeniumdiolate nitric oxide (NO) donors. A wide range of NO storage capacities (∼1-2.50 μmol mg) and NO-release kinetics (t ∼30-80 min) were achieved by changing the extent of propylene oxide (PO) modification. The therapeutic potential of these materials was evaluated by studying their antibacterial activities and toxicity against common dental pathogens and human gingival fibroblast cells, respectively. Our results indicate that the combination of NO release and PO modification is necessary to yield h-PAMAM materials with efficient bactericidal action without eliciting unwarranted cytotoxicity. Of importance, NO-releasing PO-modified h-PAMAM polymers exhibited comparable biological properties (i.e., antibacterial action and cytotoxicity) to defect-free G3-PAMAM dendrimers, but at a substantially lower synthetic burden.
Topics: Anti-Bacterial Agents; Azo Compounds; Bacteria; Bacterial Infections; Cell Line; Dendrimers; Humans; Microbial Sensitivity Tests; Nitric Oxide Donors; Structure-Activity Relationship
PubMed: 29243926
DOI: 10.1021/acs.bioconjchem.7b00537 -
Angewandte Chemie (International Ed. in... Jan 2017The p300/CBP-associated factor (PCAF) and related GCN5 bromodomain-containing lysine acetyl transferases are members of subfamily I of the bromodomain phylogenetic...
The p300/CBP-associated factor (PCAF) and related GCN5 bromodomain-containing lysine acetyl transferases are members of subfamily I of the bromodomain phylogenetic tree. Iterative cycles of rational inhibitor design and biophysical characterization led to the discovery of the triazolopthalazine-based L-45 (dubbed L-Moses) as the first potent, selective, and cell-active PCAF bromodomain (Brd) inhibitor. Synthesis from readily available (1R,2S)-(-)-norephedrine furnished L-45 in enantiopure form. L-45 was shown to disrupt PCAF-Brd histone H3.3 interaction in cells using a nanoBRET assay, and a co-crystal structure of L-45 with the homologous Brd PfGCN5 from Plasmodium falciparum rationalizes the high selectivity for PCAF and GCN5 bromodomains. Compound L-45 shows no observable cytotoxicity in peripheral blood mononuclear cells (PBMC), good cell-permeability, and metabolic stability in human and mouse liver microsomes, supporting its potential for in vivo use.
Topics: Azo Compounds; Dose-Response Relationship, Drug; Drug Discovery; Hydralazine; Molecular Probes; Molecular Structure; Structure-Activity Relationship; p300-CBP Transcription Factors
PubMed: 27966810
DOI: 10.1002/anie.201610816 -
Advanced Science (Weinheim,... May 2022In this work, a real-time precise electrical method to directly monitor the stochastic binding dynamics of a single supramolecule based on the host-guest interaction...
In this work, a real-time precise electrical method to directly monitor the stochastic binding dynamics of a single supramolecule based on the host-guest interaction between a cyclodextrin and an azo compound is reported. Different intermolecular binding states during the binding process are distinguished by conductance signals detected from graphene-molecule-graphene single-molecule junctions. In combination with theoretical calculations, the reciprocating and unidirectional motions in the trans form as well as the restrained reciprocating motion in the cis form due to the steric hindrance is observed, which could be reversibly switched by visible and UV irradiation. The integration of individual supramolecules into nanocircuits not only offers a facile and effective strategy to probe the dynamic process of supramolecular systems, but also paves the way to construct functional molecular devices toward real applications such as switches, sensors, and logic devices.
Topics: Azo Compounds; Cyclodextrins; Graphite; Nanotechnology; Ultraviolet Rays
PubMed: 35233985
DOI: 10.1002/advs.202200022 -
Ecotoxicology and Environmental Safety Jun 2022This study aimed to exploit the potential of Enterococcus faecalis R1107 in the bioremediation of azo dyes. The maximal decolorization of Congo Red (CR), Reactive Black...
This study aimed to exploit the potential of Enterococcus faecalis R1107 in the bioremediation of azo dyes. The maximal decolorization of Congo Red (CR), Reactive Black 5 (RB5), and Direct Black 38 (DB38) were 90.17%, 96.82%, and 81.95%, respectively, with the bacterial treatment for 48 h. 65.57% of CR and 72.64% of RB5 could be decolorized by E. faecalis R1107 within 48 h when the concentration of azo dyes increased up to 1000 mg/L. FTIR analysis confirmed that E. faecalis R1107 could effectively break down the chemical structures of three azo dyes. E. faecalis R1107 alleviated the phytotoxicity of azo dyes and improved seed germination, which contributed to the increase in the lengths of roots, stems, and leaves of Vigna radiata seedlings. Transcriptomic analysis suggested that the gene regulatory networks in E. faecalis R1107 synergistically improved the degradation and detoxification of RB5, including the major metabolic pathways, the secondary metabolism, the transport system, the amino acid metabolic pathways, and the signal transduction systems. Simulated textile effluent (STE) was used to mimic real textile effluent to evaluate the bioremediation potential of E. faecalis R1107, and 72.79% STE can be decolorized after E. faecalis R1107 treatment for 48 h. In summary, our study demonstrated that E. faecalis R1107 might be well suitable for potential applications in the bioremediation of textile effluent.
Topics: Azo Compounds; Biodegradation, Environmental; Coloring Agents; Congo Red; Enterococcus faecalis; Textile Industry; Textiles
PubMed: 35526458
DOI: 10.1016/j.ecoenv.2022.113577 -
Journal of Industrial Microbiology &... Dec 2009The capability of Lactobacillus acidophilus and Lactobacillus fermentum to degrade azo dyes was investigated. The bacteria were incubated under anaerobic conditions in...
The capability of Lactobacillus acidophilus and Lactobacillus fermentum to degrade azo dyes was investigated. The bacteria were incubated under anaerobic conditions in the presence of 6 microg/ml Methyl Red, Ponceau BS, Orange G, Amaranth, Orange II, and Direct Blue 15; 5 microg/ml Sudan I and II; or 1.5 microg/ml Sudan III and IV in deMann-Rogosa-Sharpe broth at 37 degrees C for 36 h, and reduction of the dyes was monitored. Both bacteria were capable of degrading all of the water-soluble azo dyes to some extent. They were also able to completely reduce the oil-soluble diazo dyes Sudan III and IV but were unable to reduce the oil-soluble monoazo dyes Sudan I and II to any significant degree in the concentrations studied. Growth of the bacteria was not significantly affected by the presence of the Sudan azo dyes. Metabolites of the bacterial degradation of Sudan III and IV were isolated and identified by liquid chromatography electrospray ionization tandem mass spectrometry analyses and compared with authentic standards. Aniline and o-toluidine (2-methylaniline), both potentially carcinogenic aromatic amines, were metabolites of Sudan III and IV, respectively.
Topics: Azo Compounds; Coloring Agents; Lactobacillus acidophilus; Limosilactobacillus fermentum; Oils; Water
PubMed: 19727875
DOI: 10.1007/s10295-009-0633-9 -
TheScientificWorldJournal 2021This article includes the synthesis of heterocyclic azo dye of theophylline by coupling diazonium salt of 4-chloroaniline with theophylline which is, namely,...
This article includes the synthesis of heterocyclic azo dye of theophylline by coupling diazonium salt of 4-chloroaniline with theophylline which is, namely, 8-(1-(4-chlorophenyl)azo)theophylline (CPAT). The complexes of cobalt and nickel were prepared by reacting their ions with CPAT ligand in ethanol under 1 : 2 ratio metal-ligand. The CPAT ligand and its complexes were characterized by elemental analysis, infrared spectrometry, electronic absorption spectroscopy, molar conductivity, and magnetic moment. The cobalt and nickel complexes show octahedral geometry having general formula [M(CPAT)Cl]. This article addresses the properties of CPAT dye such as photochromic properties. The CPAT dye exhibited obvious and desired changes under irradiation with visible light (405 nm), high sensitive for pH changes which refer to its ability to be analysis indicator. CPAT dye exhibited solvatochromic properties presenting red shift with polar solvent. The CPAT and its complexes show interesting antibiological activities towards and bacteria and fungi.
Topics: Anti-Infective Agents; Aspergillus; Azo Compounds; Escherichia coli; Hydrogen-Ion Concentration; Light; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Staphylococcus aureus; Theophylline; X-Ray Diffraction
PubMed: 34335115
DOI: 10.1155/2021/9943763 -
Journal of Food and Drug Analysis Jul 2017In this study, 120 lactic acid bacterial strains from different fermented dairy products as well as 10 bacterial intestinal isolates were evaluated for in vitro and...
In this study, 120 lactic acid bacterial strains from different fermented dairy products as well as 10 bacterial intestinal isolates were evaluated for in vitro and in vivo degradation of various food azo dyes. Of these isolates, lactic acid bacteria (LAB) strains 13 and 100 and the intestinal isolates Ent2 and Eco5 exhibited 96-98% degradation of the tested food azo dyes within 5-6 hours. High performance liquid chromatography mass spectra of sunset yellow (E110) and carmoisine (E122) anaerobic degradation products by the intestinal isolates showed that they were structurally related to toxic aromatic amines. For an in vivo study, eight groups of rats were treated for 90 days with either the food azo dyes or their degradation products. All groups were kept for a further 30 days as recovery period and then dissected at 120 days. Hematological, histopathological, and protein markers were assessed. Rats treated with either E110/E122 or their degradation products exhibited highly significant changes in red blood cell count, hemoglobin, hematocrit, mean corpuscular volume, mean corpuscular hemoglobin, mean corpuscular hemoglobin concentration, and white blood cell count. In addition, alanine and aspartate aminotransferases, amylase, total bilirubin, blood urea nitrogen, creatinine, glucose, total protein, and globulins were significantly increased. Furthermore, marked histopathological alterations in the liver, kidney, spleen, and small intestine were observed. Significant decreases in inflammation and a noticeable improvement in the liver, kidney, spleen, and small intestine of rats treated with LAB and food azo dyes simultaneously were observed. Finally, these results provide a reliable basis for not only a better understanding of the histological and biochemical effects of food additives, but also for early diagnostics. In addition, LAB strains 13 and 100 may play an important role as potential probiotics in food and dairy technology as a probiotic lactic acid starter.
Topics: Animal Feed; Animals; Azo Compounds; Coloring Agents; Cultured Milk Products; Lactobacillaceae; Probiotics; Rats
PubMed: 28911652
DOI: 10.1016/j.jfda.2017.01.005 -
Molecules (Basel, Switzerland) Oct 2022Novel yellow azo pyridone dye derivatives were synthesized for use in image-sensor color filters. The synthesized compounds have a basic chemical structure composed of...
Novel yellow azo pyridone dye derivatives were synthesized for use in image-sensor color filters. The synthesized compounds have a basic chemical structure composed of azo, hydroxy, amide, and nitrile groups as well as different halide groups. New materials were evaluated on the basis of their optical, thermal, and surface properties under conditions mimicking those of a commercial device fabrication process. A comparison of their related performance revealed that, among the four prepared compounds, 5-((4,6-dichlorocyclohexa-2,4-dien-1-yl)diazenyl)-6-hydroxy-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (Cl-PAMOPC) exhibited the best performance as an image-sensor color filter material, including a solubility greater than 0.1 wt% in propylene glycol monomethyl ether acetate solvent, a high decomposition temperature of 263 °C, and stable color difference values of 4.93 and 3.88 after a thermal treatment and a solvent-resistance test, respectively. The results suggest that Cl-PAMOPC can be used as a green dye additive in an image-sensor colorant.
Topics: Acetates; Amides; Azo Compounds; Color; Coloring Agents; Dihydropyridines; Inorganic Chemicals; Nitriles; Pyridones; Solvents
PubMed: 36235139
DOI: 10.3390/molecules27196601 -
The Journal of Physical Chemistry. B Sep 2018Over the past two decades, two-dimensional infrared (2D IR) spectroscopy has evolved from the theoretical underpinnings of nonlinear spectroscopy as a means of... (Review)
Review
Over the past two decades, two-dimensional infrared (2D IR) spectroscopy has evolved from the theoretical underpinnings of nonlinear spectroscopy as a means of investigating detailed molecular structure on an ultrafast time scale. The combined time and spectral resolution over which spectra can be collected on complex molecular systems has led to the precise structural resolution of dynamic species that have previously been impossible to directly observe through traditional methods. The adoption of 2D IR spectroscopy for the study of protein folding and peptide interactions has provided key details of how small changes in conformations can exert major influences on the activities of these complex molecular systems. Traditional 2D IR experiments are limited to molecules under equilibrium conditions, where small motions and fluctuations of these larger molecules often still lead to functionality. Utilizing techniques that allow the rapid initiation of chemical or structural changes in conjunction with 2D IR spectroscopy, i.e., transient 2D IR, a vast dynamic range becomes available to the spectroscopist uncovering structural content far from equilibrium. Furthermore, this allows the observation of reaction pathways of these macromolecules under quasi- and nonequilibrium conditions.
Topics: Azo Compounds; Disulfides; Heterocyclic Compounds, 1-Ring; Peptides; Protein Conformation; Protein Folding; Spectrophotometry, Infrared; Temperature
PubMed: 30040900
DOI: 10.1021/acs.jpcb.8b05063 -
The Journal of Physical Chemistry... Jul 2021The determination of electronic excited state (ES) properties is the cornerstone of theoretical photochemistry. Yet, traditional ES methods become impractical when...
The determination of electronic excited state (ES) properties is the cornerstone of theoretical photochemistry. Yet, traditional ES methods become impractical when applied to fairly large molecules, or when used on thousands of systems. Machine learning (ML) techniques have demonstrated their accuracy at retrieving ES properties of large molecular databases at a reduced computational cost. For these applications, nonlinear algorithms tend to be specialized in targeting individual properties. Learning fundamental quantum objects potentially represents a more efficient, yet complex, alternative as a variety of molecular properties could be extracted through postprocessing. Herein, we report a general framework able to learn three fundamental objects: the hole and particle densities, as well as the transition density. We demonstrate the advantages of targeting those outputs and apply our predictions to obtain properties, including the state character and the exciton topological descriptors, for the two bands (nπ* and ππ*) of 3427 azoheteroarene photoswitches.
Topics: Azo Compounds; Coloring Agents; Machine Learning; Models, Molecular; Molecular Conformation; Quantum Theory
PubMed: 34157226
DOI: 10.1021/acs.jpclett.1c01425