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European Journal of Pharmacology Jan 2023NMDA receptors play critical roles in numerous physiological and pathological processes in CNS that requires development of modulating ligands. In particular,...
NMDA receptors play critical roles in numerous physiological and pathological processes in CNS that requires development of modulating ligands. In particular, photoswitchable compounds that selectively target NMDA receptors would be particularly useful for analysis of receptor contributions to various processes. Recently, we identified a light-dependent anti-NMDA activity of the azobenzene-containing quaternary ammonium compounds DENAQ (diethylamine-azobenzene-quaternary ammonium) and DMNAQ (dimethylamine-azobenzene-quaternary ammonium). Here, we developed a series of light-sensitive compounds based on the DENAQ structure, and studied their action on glutamate receptors in rat brain neurons using patch-clamp method. We found that the activities of the compounds and the influence of illumination strongly depended on the structural details, as even minor structural modifications greatly altered the activity and sensitivity to illumination. The compound PyrAQ (pyrrolidine-azobenzene-quaternary ammonium) was the most active and produced fast and fully reversible inhibition of NMDA receptors. The IC values under ambient and monochromic light conditions were 2 and 14 μM, respectively. The anti-AMPA activity was much weaker. The action of PyrAQ did not depend on NMDA receptor activity, agonist concentration, or membrane voltage, making it a useful tool for photopharmacological studies.
Topics: Animals; Rats; Ammonium Compounds; Azo Compounds; Receptors, Glutamate; Receptors, N-Methyl-D-Aspartate
PubMed: 36470444
DOI: 10.1016/j.ejphar.2022.175448 -
Soft Matter Jan 2023Fluorescent protein biomaterials have important applications such as bioimaging in pharmacological studies. Self-assembly of proteins, especially into fibrils, is known...
Fluorescent protein biomaterials have important applications such as bioimaging in pharmacological studies. Self-assembly of proteins, especially into fibrils, is known to produce fluorescence in the blue band. Capable of self-assembly into nanofibers, we have shown we can modulate its aggregation into mesofibers by encapsulation of a small hydrophobic molecule. Conversely, azobenzenes are hydrophobic small molecules that are virtually non-fluorescent in solution due to their highly efficient photoisomerization. However, they demonstrate fluorogenic properties upon confinement in nanoscale assemblies by reducing the non-radiative photoisomerization. Here, we report the fluorescence of a hybrid protein-small molecule system in which azobenzene is confined in our protein assembly leading to fiber thickening and increased fluorescence. We show our engineered protein Q encapsulates AzoCholine, bearing a photoswitchable azobenzene moiety, in the hydrophobic pore to produce fluorescent mesofibers. This study further investigates the photocontrol of protein conformation as well as fluorescence of an azobenze-containing biomaterial.
Topics: Proteins; Protein Conformation; Azo Compounds
PubMed: 36538008
DOI: 10.1039/d2sm01578a -
Chemosphere Feb 2023Development of science has taken over our lives and made it mandatory to live with science. Synthetic technology takes more than it has given for our welfare. In the... (Review)
Review
Development of science has taken over our lives and made it mandatory to live with science. Synthetic technology takes more than it has given for our welfare. In the process of meeting the demand of the consumers, industries supported synthetic products to meet the same. One such sector that employs synthetic azo dyes for food coloring is the food industry. The result of the process is the production of a variety of colored foods which looks more appealing and palatable. The process not only meets the consumer's demand it also has an impact on customers' health because the consumption of azo-toxic dye-treated foods regularly or in direct contact with synthetic azo dyes can also cause severe human health consequences. Nanotechnology is a rapidly evolving branch of research in which nanosensors are being developed for a variety of applications, including sensing various azo-toxic dyes in food products, which provides a wider scope in the future, with the innovation in designing different nanosensors. The current review focuses on the different types of nanosensors, their key role in sensing, and the sensing of azo toxic dyes using nanosensors, their advantages over other sensors, applications of nanomaterials, and the health impacts of azo dyes on humans, appropriate parameters for maximum permissible limits, and an Acceptable Daily Intake (ADI) of azo toxic dye to be followed. The regulations followed on the application of colorants to the food are also elaborated. The review also focuses on the application of enzyme-based biosensors in detecting azo dyes in food products.
Topics: Humans; Coloring Agents; Azo Compounds; Nanostructures; No-Observed-Adverse-Effect Level
PubMed: 36565768
DOI: 10.1016/j.chemosphere.2022.137614 -
Molecules (Basel, Switzerland) Aug 2021Synthetic heterocyclic compounds have incredible potential against different diseases; pyridines, phenolic compounds and the derivatives of azo moiety have shown... (Review)
Review
Synthetic heterocyclic compounds have incredible potential against different diseases; pyridines, phenolic compounds and the derivatives of azo moiety have shown excellent antimicrobial, antiviral, antidiabetic, anti-melanogenic, anti-ulcer, anticancer, anti-mycobacterial, anti-inflammatory, DNA binding and chemosensing activities. In the present review, the above-mentioned activities of the nitrogen-containing heterocyclic compounds (pyridines), hydroxyl (phenols) and azo derivatives are discussed with reference to the minimum inhibitory concentration and structure-activity relationship, which clearly indicate that the presence of nitrogen in the phenyl ring; in addition, the hydroxyl substituent and the incorporation of a diazo group is crucial for the improved efficacies of the compounds in probing different diseases. The comparison was made with the reported drugs and new synthetic derivatives that showed recent therapeutic perspectives made in the last five years.
Topics: Azo Compounds; Imaging, Three-Dimensional; Phenols; Pyridines
PubMed: 34443460
DOI: 10.3390/molecules26164872 -
Chemical Communications (Cambridge,... Oct 2021RNA is an emerging drug target that opens new perspectives in the treatment of viral and bacterial infections, cancer and a range of so far incurable genetic diseases.... (Review)
Review
RNA is an emerging drug target that opens new perspectives in the treatment of viral and bacterial infections, cancer and a range of so far incurable genetic diseases. Among the various strategies towards the design and development of selective and efficient ligands for targeting and detection of therapeutically relevant RNA, photoswitchable RNA binders represent a very promising approach due to the possibility to control the ligand-RNA and protein-RNA interactions by light with high spatiotemporal resolution. However, the field of photoswitchable RNA binders still remains underexplored due to challenging design of lead structures that should combine high RNA binding selectivity with efficient photochemical performance. The aim of this highlight article is to describe the development of photoswitchable noncovalent RNA binders and to outline the current situation and perspectives of this emerging interdisciplinary field.
Topics: Azo Compounds; Benzylidene Compounds; HIV; Humans; Ligands; Light; RNA; Stereoisomerism
PubMed: 34585681
DOI: 10.1039/d1cc04241f -
Angewandte Chemie (International Ed. in... Nov 2022This study presents interesting self-assembly of peapod-like micrometer tubes from a planet-satellite-type supramolecular megamer, which was constructed through the...
This study presents interesting self-assembly of peapod-like micrometer tubes from a planet-satellite-type supramolecular megamer, which was constructed through the specific host-guest molecular recognition between azobenzene (AZO)-functionalized hyperbranched poly(ethyl-3-oxetanemethanol)-star-poly(ethylene oxide) (HSP-AZO) and β-cyclodextrin(CD)-based hydrophilic hyperbranched polyglycerol (CD-g-HPG). A peapod-like structure with micrometer-sized tube as the pod and vesicles encapsulated inside as the peas was formed through sequential vesicle entosis, linear association, and fusion processes. Dissipative particle dynamics (DPD) simulations support the structural possibility of the supramolecular peapod formation and its mechanism. UV light irradiation could lead to the disassembly of the peapod-like structure. This study expands the family of supramolecular polymers and opens a new avenue to develop bioinspired complex hierarchical nanoarchitectures at the microscopic level.
Topics: Planets; Azo Compounds; Hydrophobic and Hydrophilic Interactions; Polyethylene Glycols
PubMed: 36131490
DOI: 10.1002/anie.202213178 -
Organic & Biomolecular Chemistry Jan 2022Amphiphilic polymers can self-assemble to form nanoparticles with different structures under suitable conditions. Polymer nanoparticles functionalized with aromatic azo... (Review)
Review
Amphiphilic polymers can self-assemble to form nanoparticles with different structures under suitable conditions. Polymer nanoparticles functionalized with aromatic azo groups are endowed with photo-responsive properties. In recent years, a variety of photoresponsive polymers and nanoparticles have been developed based on azobenzene, using different molecular design strategies and synthetic routes. This article reviews the progress of this rapidly developing research field, focusing on the structure, synthesis, assembly and response of photo-responsive polymer assemblies. According to the molecular structure, photo-responsive polymers can be divided into linear polymers containing azobenzene in a side chain, linear polymers containing azobenzene in the main chain, linear polymers containing azobenzene in an end group, branched polymers containing azobenzene and supramolecular polymers containing azobenzene. These systems have broad biomedical application prospects in the field of drug delivery and imaging applications.
Topics: Azo Compounds; Drug Delivery Systems; Nanostructures; Optical Imaging; Polymers
PubMed: 34908082
DOI: 10.1039/d1ob01823j -
Archives of Microbiology Jul 2022Textile wastewater contains dyes mixed with other contaminants in various concentrations. Bacteria-mediated decolorization and degradation of azo dyes have achieved...
Textile wastewater contains dyes mixed with other contaminants in various concentrations. Bacteria-mediated decolorization and degradation of azo dyes have achieved momentum as a method of treatment attributed to their inexpensive, eco-friendly, and application to a wide range of azo dyes. However, a single species of bacteria is inefficient in decolorizing diverse groups of dyes which is one of the most significant challenges for environmental technologists working in bioremediation. In the present study, an aerobic bacterial consortium AUJ consisting of six different bacterial strains (Pseudomonas stutzeri AK1, Pseudomonas stutzeri AK2, Pseudomonas stutzeri AK3, Bacillus spp. AK4, Pseudomonas stutzeri AK5, and Pseudomonas stutzeri AK6) removed the individual azo dyes in the 24-94% range when used in more than 200 ppm concentration within 72-96 h. In addition, the consortium was able to decolorize 52.19% mixed dyes (100 ppm) and 44.55% Acid blue 113 when used at a concentration as high as 1100 ppm within 96 h. Optimization of various nutritional and environmental parameters revealed that glucose and yeast extract were the preferred carbon and nitrogen source, respectively, and analysis of treated dye products using high-performance liquid chromatography (HPLC), Fourier-transform infrared spectroscopy (FTIR), and gas chromatography-mass spectrometry (GC-MS) confirmed the breakdown of dye. In all, we present a bacterial consortium with a good ability of dye decolorization that can be used for degrading a wide variety of azo dyes.
Topics: Azo Compounds; Bacteria; Biodegradation, Environmental; Coloring Agents; Wastewater
PubMed: 35867172
DOI: 10.1007/s00203-022-03108-0 -
Mutation Research. Genetic Toxicology... Aug 2019The mutagenicity of Direct Black 38, Sudan I, and Para Red were evaluated in the in vivo MutaMouse assay and the in vitro MutaMouse primary hepatocyte (PH) assay. Direct...
The mutagenicity of Direct Black 38, Sudan I, and Para Red were evaluated in the in vivo MutaMouse assay and the in vitro MutaMouse primary hepatocyte (PH) assay. Direct Black 38 is an International Agency for Research on Cancer (IARC) Group 1 carcinogen and a prototypical benzidine-based azo compound that requires azo-reduction to yield a DNA-reactive metabolite. Sudan I and Para Red are structurally related azo compounds that have been detected as illegal contaminants in foods. Sudan I is an in vivo mutagen, and both it and Para Red are known to be mutagenic in vitro. Sudan I is oxidized by hepatic and/or bladder enzymes to yield a mutagenic metabolite, but little is known about Para Red. In the present study, Direct Black 38 elicited a significant mutagenic response in the bone marrow, glandular stomach, small intestine and colon in vivo, and in PHs in vitro. Sudan I elicited a weak positive response in the bone marrow and a marginally significant treatment effect in the bladder (p = 0.059); it did not elicit a significant response in PHs in vitro. Para Red elicited a positive response in the colon, as well as in PHs in vitro, albeit at a cytotoxic concentration. The findings are well aligned with the known mechanisms of action of Direct Black 38 and Sudan I; they suggest that intestinal azo-reduction plays an important role in the activation of Para Red. The MutaMouse pH results illustrate the ability of this assay to detect chemicals requiring azo-reduction; however, they also demonstrate a gap in applicability domain, as MutaMouse PHs elicit a negative response following exposure to Sudan I. Elucidation of the mechanisms underlying this gap will require further study.
Topics: Animals; Azo Compounds; Cells, Cultured; Hepatocytes; Mice; Mutagenicity Tests; Mutagens; Naphthols; Organ Specificity; Primary Cell Culture; Structure-Activity Relationship
PubMed: 31326032
DOI: 10.1016/j.mrgentox.2019.06.003 -
Angewandte Chemie (International Ed. in... May 2020Mass spectrometry (MS)-based proteomics provides unprecedented opportunities for understanding the structure and function of proteins in complex biological systems;...
Mass spectrometry (MS)-based proteomics provides unprecedented opportunities for understanding the structure and function of proteins in complex biological systems; however, protein solubility and sample preparation before MS remain a bottleneck preventing high-throughput proteomics. Herein, we report a high-throughput bottom-up proteomic method enabled by a newly developed MS-compatible photocleavable surfactant, 4-hexylphenylazosulfonate (Azo) that facilitates robust protein extraction, rapid enzymatic digestion (30 min compared to overnight), and subsequent MS-analysis following UV degradation. Moreover, we developed an Azo-aided bottom-up method for analysis of integral membrane proteins, which are key drug targets and are generally underrepresented in global proteomic studies. Furthermore, we demonstrated the ability of Azo to serve as an "all-in-one" MS-compatible surfactant for both top-down and bottom-up proteomics, with streamlined workflows for high-throughput proteomics amenable to clinical applications.
Topics: Azo Compounds; Light; Proteolysis; Proteomics; Surface-Active Agents
PubMed: 32097521
DOI: 10.1002/anie.201915374