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British Journal of Pharmacology Jul 2017Azoreductases are flavoenzymes that have been characterized in a range of prokaryotes and eukaryotes. Bacterial azoreductases are associated with the activation of two... (Review)
Review
UNLABELLED
Azoreductases are flavoenzymes that have been characterized in a range of prokaryotes and eukaryotes. Bacterial azoreductases are associated with the activation of two classes of drug, azo drugs for the treatment of inflammatory bowel disease and nitrofuran antibiotics. The mechanism of reduction of azo compounds is presented; it requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo and quinone substrates by azoreductases. The importance of further work in the characterization of azoreductases from enteric bacteria is highlighted to aid in the development of novel drugs for the treatment of colon related disorders. Human azoreductases are known to play a crucial role in the metabolism of a number of quinone-containing cancer chemotherapeutic drugs. The mechanism of hydride transfer to quinones, which is shared not only between eukaryotic and prokaryotic azoreductases but also the wider family of NAD(P)H quinone oxidoreductases, is outlined. The importance of common single nucleotide polymorphisms (SNPs) in human azoreductases is described not only in cancer prognosis but also with regard to their effects on the efficacy of quinone drug-based cancer chemotherapeutic regimens. This highlights the need to screen patients for azoreductase SNPs ahead of treatment with these regimens.
LINKED ARTICLES
This article is part of a themed section on Drug Metabolism and Antibiotic Resistance in Micro-organisms. To view the other articles in this section visit http://onlinelibrary.wiley.com/doi/10.1111/bph.v174.14/issuetoc.
Topics: Anti-Bacterial Agents; Antineoplastic Agents; Azo Compounds; Bacteria; Humans; NADH, NADPH Oxidoreductases; Neoplasms; Nitrofurans; Nitroreductases; Quinones
PubMed: 27487252
DOI: 10.1111/bph.13571 -
Molecules (Basel, Switzerland) Sep 2022Azo molecules, characterized by the presence of a -N=N- double bond, are widely used in various fields due to their sensitivity to external stimuli, ch as light. The... (Review)
Review
Azo molecules, characterized by the presence of a -N=N- double bond, are widely used in various fields due to their sensitivity to external stimuli, ch as light. The emergence of bacterial resistance has pushed research towards designing new antimicrobial molecules that are more efficient than those currently in use. Many authors have attempted to exploit the antimicrobial activity of azobenzene and to utilize their photoisomerization for selective control of the bioactivities of antimicrobial molecules, which is necessary for antibacterial therapy. This review will provide a systematic and consequential approach to coupling azobenzene moiety with active antimicrobial molecules and drugs, including small and large organic molecules, such as peptides. A selection of significant cutting-edge articles collected in recent years has been discussed, based on the structural pattern and antimicrobial performance, focusing especially on the photoactivity of azobenzene and the design of smart materials as the most targeted and desirable application.
Topics: Anti-Bacterial Agents; Anti-Infective Agents; Azo Compounds
PubMed: 36080413
DOI: 10.3390/molecules27175643 -
Bioresource Technology Oct 2020Industrialization increases use of dyes due to its high demand in paper, cosmetic, textile, leather and food industries. This in turn would increase wastewater... (Review)
Review
Industrialization increases use of dyes due to its high demand in paper, cosmetic, textile, leather and food industries. This in turn would increase wastewater generation from dye industrial activities. Various dyes and its structural compounds present in dye industrial wastewater have harmful effects on plants, animals and humans. Synthetic dyes are more resistant than natural dyes to physical and chemical methods for remediation which makes them more difficult to get decolorize. Microbial degradation has been researched and reviewed largely for quicker dye degradation. Genetically engineered microorganisms (GEMs) play important role in achieving complete dye degradation. This paper provides scientific and technical information about dyes & dye intermediates and biodegradation of azo dye. It also compiles information about factors affecting dye(s) biodegradation, role of genetically modified organisms (GMOs) in process of dye(s) degradation and perspectives in this field of research.
Topics: Animals; Azo Compounds; Biodegradation, Environmental; Coloring Agents; Humans; Textile Industry; Textiles; Wastewater
PubMed: 32665105
DOI: 10.1016/j.biortech.2020.123728 -
Journal of Visualized Experiments : JoVE Mar 2018Caenorhabditis elegans is an exceptional model organism in which to study lipid metabolism and energy homeostasis. Many of its lipid genes are conserved in humans and...
Caenorhabditis elegans is an exceptional model organism in which to study lipid metabolism and energy homeostasis. Many of its lipid genes are conserved in humans and are associated with metabolic syndrome or other diseases. Examination of lipid accumulation in this organism can be carried out by fixative dyes or label-free methods. Fixative stains like Nile red and oil red O are inexpensive, reliable ways to quantitatively measure lipid levels and to qualitatively observe lipid distribution across tissues, respectively. Moreover, these stains allow for high-throughput screening of various lipid metabolism genes and pathways. Additionally, their hydrophobic nature facilitates lipid solubility, reduces interaction with surrounding tissues, and prevents dissociation into the solvent. Though these methods are effective at examining general lipid content, they do not provide detailed information about the chemical composition and diversity of lipid deposits. For these purposes, label-free methods such as GC-MS and CARS microscopy are better suited, their costs notwithstanding.
Topics: Animals; Azo Compounds; Caenorhabditis elegans; Lipid Metabolism; Lipids; Oxazines; Staining and Labeling
PubMed: 29553519
DOI: 10.3791/57352 -
The Journal of Histochemistry and... Oct 2021Collagen has a major role in the structural organization of tendons. Picrosirius red (PSR) staining viewed under polarized light microscopy is the standard method to...
Collagen has a major role in the structural organization of tendons. Picrosirius red (PSR) staining viewed under polarized light microscopy is the standard method to evaluate the organization of collagen fibers in tissues. It is also used to distinguish between type I and type III collagen in tissue sections. However, accurate analysis and interpretation of PSR images are challenging because of technical factors and historical misconceptions. The aim of this study was to clarify whether collagen types I and III can be distinguished by PSR staining in rat Achilles tendons, using double immunohistochemistry as the positive control. Our findings showed that PSR staining viewed with polarized light microscopy was suitable for qualitative and quantitative assessment of total collagen but was not able to distinguish collagen types. We found it critical to use a polarizing microscope equipped with a rotating stage; tendon section orientation at 45° with respect to crossed polarizers was optimal for the qualitative and quantitative assessment of collagen organization. Immunohistochemistry was superior to PSR staining for detection of collagen type III. We also compared formalin and Bouin solution as fixatives. Both produced similar birefringence, but formalin-fixed tendons provided higher quality histological detail with both hematoxylin-eosin and immunostaining.
Topics: Animals; Azo Compounds; Collagen Type I; Collagen Type III; Rats; Rats, Sprague-Dawley; Staining and Labeling; Tendons
PubMed: 34549650
DOI: 10.1369/00221554211046777 -
Molecules (Basel, Switzerland) Jan 2020Several series of natural polyphenols are described for their biological and therapeutic potential. Natural stilbenoid polyphenols, such as trans-resveratrol,... (Review)
Review
Several series of natural polyphenols are described for their biological and therapeutic potential. Natural stilbenoid polyphenols, such as trans-resveratrol, pterostilbene and piceatannol are well-known for their numerous biological activities. However, their moderate bio-availabilities, especially for trans-resveratrol, prompted numerous research groups to investigate innovative and relevant synthetic resveratrol derivatives. This review is focused on isosteric resveratrol analogs aza-stilbenes and azo-stilbenes in which the C=C bond between both aromatic rings was replaced with C=N or N=N bonds, respectively. In each series, synthetic ways will be displayed, and structural sights will be highlighted and compared with those of resveratrol. The biological activities of some of these molecules will be presented as well as their potential therapeutic applications. In some cases, structure-activity relationships will be discussed.
Topics: Antioxidants; Aza Compounds; Azo Compounds; Molecular Structure; Resveratrol; Stereoisomerism; Stilbenes; Structure-Activity Relationship
PubMed: 32019195
DOI: 10.3390/molecules25030605 -
International Journal of Environmental... Apr 2022Azo dyes have become a staple in various industries, as colors play an important role in consumer choices. However, these dyes pose various health and environmental... (Review)
Review
Azo dyes have become a staple in various industries, as colors play an important role in consumer choices. However, these dyes pose various health and environmental risks. Although different wastewater treatments are available, the search for more eco-friendly options persists. Bioremediation utilizing microorganisms has been of great interest to researchers and industries, as the transition toward greener solutions has become more in demand through the years. This review tackles the health and environmental repercussions of azo dyes and its metabolites, available biological approaches to eliminate such dyes from the environment with a focus on the use of different microorganisms, enzymes that are involved in the degradation of azo dyes, and recent trends that could be applied for the treatment of azo dyes.
Topics: Azo Compounds; Biodegradation, Environmental; Coloring Agents
PubMed: 35457607
DOI: 10.3390/ijerph19084740 -
Chemical & Pharmaceutical Bulletin 2021The ability to control the reactions of highly active chemical species to enable straightforward synthesis of valuable compounds such as bioactive natural products and... (Review)
Review
The ability to control the reactions of highly active chemical species to enable straightforward synthesis of valuable compounds such as bioactive natural products and pharmaceuticals is a continuing challenge in synthetic organic chemistry. This review describes the development of a methodology using reactive metal-carbene species and its synthetic application in our laboratory. First, regioselective synthesis of γ-amino acid equivalents to take advantage of their metal-dependent reactivities and the mechanistic rationale are presented. Chemoselective and enantioselective dearomatization reactions of several arenes with silver-carbene are also discussed. In the second half of the review, we discuss a carbene-insertion reaction into an amide and urea C-N bond for the assembly of nitrogen-bridged cyclic molecules.
Topics: Azo Compounds; Catalysis; Metals, Heavy; Methane
PubMed: 34853283
DOI: 10.1248/cpb.c21-00757 -
Contact Dermatitis Oct 2022Azobenzene disperse dyes (azo DDs) are well-known as textile allergens, but the knowledge of their occurrence in garments is low. The numerous azo DDs and dye components...
BACKGROUND
Azobenzene disperse dyes (azo DDs) are well-known as textile allergens, but the knowledge of their occurrence in garments is low. The numerous azo DDs and dye components found in textiles constitute a potential health risk, but only seven azo DDs are included in the European baseline patch test series (EBS).
OBJECTIVES
To investigate non-regulated azo DDs and dye components in synthetic garments on the Swedish market.
METHODS
High-performance liquid chromatography/mass spectrometry, gas chromatography/mass spectrometry and computerized data mining.
RESULTS
Sixty-two azo DDs were detected, with Disperse Red 167:1 occurring in 67%, and 14 other DDs each found in >20% of the garments. Notably, the EBS dyes were less common, three even not detected, while arylamines were frequently detected and exceeded 1 mg/g in several garments. Also, halogenated dinitrobenzenes were identified in 25% of the textiles.
CONCLUSION
Azo DDs and dye components, in complex compositions and with large variations, occurred frequently in the synthetic garments. The arylamines were shown to occur at much higher levels compared to the azo DDs, suggesting the former constitute a potentially higher health risk. The role of arylamines and halogenated dinitrobenzenes in textile allergy has to be further investigated.
Topics: Allergens; Amines; Azo Compounds; Clothing; Coloring Agents; Dermatitis, Allergic Contact; Dinitrobenzenes; Humans; Patch Tests; Sweden; Textiles
PubMed: 35611449
DOI: 10.1111/cod.14163 -
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