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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 -
Food Chemistry Feb 2016A wide variety of azo dyes are generally added for coloring food products not only to make them visually aesthetic but also to reinstate the original appearance lost... (Review)
Review
A wide variety of azo dyes are generally added for coloring food products not only to make them visually aesthetic but also to reinstate the original appearance lost during the production process. However, many countries in the world have banned the use of most of the azo dyes in food and their usage is highly regulated by domestic and export food supplies. The regulatory authorities and food analysts adopt highly sensitive and selective analytical methods for monitoring as well as assuring the quality and safety of food products. The present manuscript presents a comprehensive review of various analytical techniques used in the analysis of azo dyes employed in food industries of different parts of the world. A brief description on the use of different extraction methods such as liquid-liquid, solid phase and membrane extraction has also been presented.
Topics: Azo Compounds; Chromatography, Liquid; Food Industry; Mass Spectrometry
PubMed: 26304415
DOI: 10.1016/j.foodchem.2015.07.085 -
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 -
Molecular Imaging and Biology Aug 2014The aim of the present study was to develop short half-lived tools for in vitro and in vivo β-amyloid imaging in mice, for which no suitable PET tracers are available.
PURPOSE
The aim of the present study was to develop short half-lived tools for in vitro and in vivo β-amyloid imaging in mice, for which no suitable PET tracers are available.
PROCEDURES
Five (13)N-labelled azo compounds (1-5) were synthesized using a three-step process using cyclotron-produced [(13)N]NO3 (-). Biodistribution studies were performed using positron emission tomography-computed tomography (PET-CT) on 20-month-old healthy, wild-type (WT) mice. In vivo and in vitro binding assays were performed using PET-CT and autoradiography, respectively, on 20-month-old healthy (WT) mice and transgenic (Tg2576) Alzheimer's disease model mice.
RESULTS
(13)N-labelled azo compounds were prepared with decay corrected radiochemical yields in the range 27 ± 4 % to 39 ± 4 %. Biodistribution studies showed good blood-brain barrier penetration for compounds 1 and 3-5; good clearance data were also obtained for compounds 1-3 and 5. Compounds 2, 3 and 5 (but not 1) showed a significant uptake in β-amyloid-rich structures when assayed in in vitro autoradiographic studies. PET studies showed significant uptake of compounds 2 and 3 in the cortex of transgenic animals that exhibit β-amyloid deposits.
CONCLUSIONS
The results underscore the potential of compounds 2 and 3 as in vitro and in vivo markers for β-amyloid in animal models of Alzheimer's disease.
Topics: Amyloid beta-Peptides; Animals; Autoradiography; Azo Compounds; Hippocampus; Ligands; Mice, Inbred C57BL; Mice, Transgenic; Nitrogen Isotopes; Positron-Emission Tomography; Tissue Distribution
PubMed: 24310721
DOI: 10.1007/s11307-013-0708-x -
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 -
Accounts of Chemical Research Oct 2015Recently, there has been a great deal of interest in using the photoisomerization of azobenzene compounds to control specific biological targets in vivo. These azo...
Recently, there has been a great deal of interest in using the photoisomerization of azobenzene compounds to control specific biological targets in vivo. These azo compounds can be used as research tools or, in principle, could act as optically controlled drugs. Such "photopharmaceuticals" offer the prospect of targeted drug action and an unprecedented degree of temporal control. A key feature of azo compounds designed to photoswitch in vivo is the wavelength of light required to cause the photoisomerization. To pass through tissue such as the human hand, wavelengths in the red, far-red, or ideally near infrared region are required. This Account describes our attempts to produce such azo compounds. Introducing electron-donating or push/pull substituents at the para positions delocalizes the azobenzene chromophore and leads to long wavelength absorption but usually also lowers the thermal barrier to interconversion of the isomers. Fast thermal relaxation means it is difficult to produce a large steady state fraction of the cis isomer. Thus, specifically activating or inhibiting a biological process with the cis isomer would require an impractically bright light source. We have found that introducing substituents at all four ortho positions leads to azo compounds with a number of unusual properties that are useful for in vivo photoswitching. When the para substituents are amide groups, these tetra-ortho substituted azo compounds show unusually slow thermal relaxation rates and enhanced separation of n-π* transitions of cis and trans isomers compared to analogues without ortho substituents. When para positions are substituted with amino groups, ortho methoxy groups greatly stabilize the azonium form of the compounds, in which the azo group is protonated. Azonium ions absorb strongly in the red region of the spectrum and can reach into the near-IR. These azonium ions can exhibit robust cis-trans isomerization in aqueous solutions at neutral pH. By varying the nature of ortho substituents, together with the number and nature of meta and para substituents, long wavelength switching, stability to photobleaching, stability to hydrolysis, and stability to reduction by thiols can all be crafted into a photoswitch. Some of these newly developed photoswitches can be used in whole blood and show promise for effective use in vivo. It is hoped they can be combined with appropriate bioactive targets to realize the potential of photopharmacology.
Topics: Animals; Azo Compounds; Humans; Photochemical Processes; Structure-Activity Relationship
PubMed: 26415024
DOI: 10.1021/acs.accounts.5b00270 -
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 -
Food and Chemical Toxicology : An... Nov 2022It is necessary to determine whether synthetic dyes are present in food since their excessive use has detrimental effects on human health. For the simultaneous...
It is necessary to determine whether synthetic dyes are present in food since their excessive use has detrimental effects on human health. For the simultaneous assessment of tartrazine and Patent Blue V, a novel electrochemical sensing platform was developed. As a result, two artificial azo colorants (Tartrazine and Patent Blue V) with toxic azo groups (-NN-) and other carcinogenic aromatic ring structures were examined. With a low limit of detection of 0.06 μM, a broad linear concentration range 0.09μM to 950μM, and a respectable recovery, scanning electron microscopy (SEM) was able to reveal the excellent sensing performance of the suggested electrode for patent blue V. The electrochemical performance of an electrode can be characterized using cyclic and differential pulse voltammetry, and electrochemical impedance spectroscopy. Moreover, the classification model was created by applying binary classification assessment using enhanced artificial intelligence comprises of support vector machine (SVM) and Genetic Algorithm (GA), respectively, a support vector machine and a genetic algorithm, which was then validated using the 50 dyes test set. The best binary logistic regression model has an accuracy of 83.2% and 81.1%, respectively, while the best SVM model has an accuracy of 90.3% for the training group of samples and 81.1% for the test group (RMSE = 0.644, R2 = 0.873, C = 205.41, and = 5.992). According to the findings, Cu-BTC MOF (copper (II)-benzene-1,3,5-tricarboxylate) has a crystal structure and is tightly packed with hierarchically porous nanomaterials, with each particle's edge measuring between 20 and 37 nm. The suggested electrochemical sensor's analytical performance is suitable for foods like jellies, condiments, soft drinks and candies.
Topics: Humans; Artificial Intelligence; Azo Compounds; Electrochemical Techniques; Electrodes; Food Coloring Agents; Food Contamination; Rosaniline Dyes; Tartrazine
PubMed: 36096291
DOI: 10.1016/j.fct.2022.113398 -
Journal of Chemical Information and... May 2019Realization of multistimuli responsiveness in one molecule remains a challenge due to the difficulty in understanding and control of comprehensive interplay between the...
Realization of multistimuli responsiveness in one molecule remains a challenge due to the difficulty in understanding and control of comprehensive interplay between the external stimuli and the subtle conformation changes. The coexistence of dynamic bonding interactions, hydroxyl group, and the azo chromophore in calcon causes the multistimuli responsiveness to external stimuli including temperature, pH variation, and light irradiation. Density functional theory (DFT), time-dependent DFT (TDDFT), and various molecular dynamics (MD) simulations are employed to systematically investigate the azo-hydrazone tautomerism and E-to- Z isomerization. The inter/intramolecular hydrogen bonding interactions promote the azo-hydrazone tautomerism at different pH conditions. The strong n → π* absorption in the visible light region gives an advantage of calcon without the harm to living cells from UV light. The facial tautomerism renders the calcon temperature sensitivity, which could be triggered at body temperature (311 K) with distinct color change from red to blue. It is also found that in pH = 6.8 both azo and hydrazone isomers have no cytotoxicity on the human lung cells (A549 and H1299) and hepatic epithelial cell of rat (FL83B). The visible-light absorption, pH, and temperature sensitiveness and biocompatibility render calcon potential candidates for biomedical applications.
Topics: A549 Cells; Animals; Azo Compounds; Density Functional Theory; Humans; Hydrazones; Hydrogen Bonding; Hydrogen-Ion Concentration; Materials Testing; Molecular Conformation; Molecular Dynamics Simulation; Rats; Stereoisomerism; Temperature
PubMed: 30769961
DOI: 10.1021/acs.jcim.8b00985 -
Chemico-biological Interactions Jul 2019Tumor hypoxia is the low tissue oxygen levels seen characteristically in rapidly proliferating and expanding neoplasms. It affects both malignant tumor cells and its... (Review)
Review
Tumor hypoxia is the low tissue oxygen levels seen characteristically in rapidly proliferating and expanding neoplasms. It affects both malignant tumor cells and its microenvironment, resulting in dysfunctional neovascularization. This leads to epithelial-to-mesenchymal transition phenotype, facilitating tumor progression through cell mobility, invasion, and metastasis. The hypoxic condition in solid tumors is thus an indicator of the process of cancer progression towards an aggressive malignant phenotype with an enhanced possibility of metastasis and resistance to treatment. Advancements in the detection of tumor hypoxia and its utilization as a treatment modality in solid tumors are highly imperative. The use of fluorescent probes is an evolving field for detecting hypoxic tumors in biological systems. The present review is an attempt to provide a contextual knowledge on the prominent role of tumor hypoxia in cancer progression and dissemination. The use of azodyes in detecting tumor hypoxia aiding in cancer diagnosis through fluorescence off-on imaging and azodye-based hypoxia selective pro-drugs for assisting cancer therapy are presented. The limitations of fluorescence based hypoxia imaging and further investigations desired for clinical usage of azodye based hypoxic probes for fluorescence imaging are also considered.
Topics: Azo Compounds; Biomarkers, Tumor; Fluorescent Dyes; Humans; Neoplasms; Photosensitizing Agents; Prodrugs; Tumor Hypoxia; Tumor Microenvironment
PubMed: 31047917
DOI: 10.1016/j.cbi.2019.04.034