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World Journal of Microbiology &... Oct 2022The consumption of foods fraught with histamine can lead to various allergy-like symptoms if the histamine is not sufficiently degraded in the human body. The... (Review)
Review
The consumption of foods fraught with histamine can lead to various allergy-like symptoms if the histamine is not sufficiently degraded in the human body. The degradation occurs primarily in the small intestine, naturally catalyzed by the human diamine oxidase (DAO). An inherent or acquired deficiency in human DAO function causes the accumulation of histamine and subsequent intrusion of histamine into the bloodstream. The histamine exerts its effects acting on different histamine receptors all over the body but also directly in the intestinal lumen. The inability to degrade sufficient amounts of dietary histamine is known as the 'histamine intolerance'. It would be preferable to solve this problem initially by the production of histamine-free or -reduced foods and by the oral supplementation of exogenous DAO supporting the human DAO in the small intestine. For the latter, DAOs from mammalian, herbal and microbial sources may be applicable. Microbial DAOs seem to be the most promising choice due to their possibility of an efficient biotechnological production in suitable microbial hosts. However, their biochemical properties, such as activity and stability under process conditions and substrate selectivity, play important roles for their successful application. This review deals with the advances and challenges of DAOs and other histamine-oxidizing enzymes for their potential application as processing aids for the production of histamine-reduced foods or as orally administered adjuvants to humans who have been eating food fraught with histamine.
Topics: Amine Oxidase (Copper-Containing); Animals; Diamines; Histamine; Humans; Mammals; Oxidation-Reduction; Receptors, Histamine
PubMed: 36208352
DOI: 10.1007/s11274-022-03421-2 -
Angewandte Chemie (International Ed. in... Oct 2022Cytochrome P450s and Galactose Oxidases exploit redox active ligands to form reactive high valent intermediates for oxidation reactions. This strategy works well for the...
Cytochrome P450s and Galactose Oxidases exploit redox active ligands to form reactive high valent intermediates for oxidation reactions. This strategy works well for the late 3d metals where accessing high valent states is rather challenging. Herein, we report the oxidation of Ni (salen) (salen=N,N'-bis(3,5-di-tert-butyl-salicylidene)-1,2-cyclohexane-(1R,2R)-diamine) with mCPBA (meta-chloroperoxybenzoic acid) to form a fleeting Ni bisphenoxyl diradical species, in CH CN and CH Cl at -40 °C. Electrochemical and spectroscopic analyses using UV/Vis, EPR, and resonance Raman spectroscopies revealed oxidation events both on the ligand and the metal centre to yield a Ni bisphenoxyl diradical species. DFT calculations found the electronic structure of the ligand and the d-configuration of the metal center to be consistent with a Ni bisphenoxyl diradical species. This three electron oxidized species can perform hydrogen atom abstraction and oxygen atom transfer reactions.
Topics: Chlorobenzoates; Cyclohexanes; Cytochromes; Diamines; Ethylenediamines; Galactose; Galactose Oxidase; Hydrogen; Ligands; Metals; Nickel; Oxidation-Reduction; Oxygen
PubMed: 35978531
DOI: 10.1002/anie.202211345 -
Canadian Journal of Veterinary Research... Jan 2022The objective of this study was to describe the histological and histochemical characteristics of the lacrimal glands of beluga whales. The study was carried out on the...
The objective of this study was to describe the histological and histochemical characteristics of the lacrimal glands of beluga whales. The study was carried out on the formalin-fixed ocular globes from 96 carcasses of beluga whales found stranded in the St. Lawrence estuary in Quebec, Canada. Hematoxylin and eosin (H&E) stained slides from the eyes of each whale were examined for lacrimal glands. Histological description was done with H&E and Masson Trichrome (MT) stains. Period Acid-Schiff (PAS), Alcian blue (AB) pH 1.0 and 2.5, and High Iron Diamine (HID) stains were used for histochemical characterization of glycoproteins. Thirteen ocular samples from animals ranging from neonate to 48 y included sections of lacrimal glands. The H&E stain revealed a tubuloalveolar gland architecture, separated into lobules by dense connective tissue. Each lobule contained a mixture of acini and tubules with ductules. Small and large acini were composed of low and tall columnar cells, respectively. Acinar cells contained basophilic cytoplasmic granules. The ductules were lined with a bi-layered cuboidal-to-squamous epithelium. The MT stain highlighted the connective tissue separating ductules and acini. Large acini were positive for PAS and some small acini had patchy uptake. Positive staining for AB pH 1.0 and 2.5 was mainly seen in tall columnar cells as compared to small acini that had faint to no stain uptake. High Iron Diamine stain revealed 90% staining of all acinar cells, with 10% exhibiting a mixed blue-black tinge. It was concluded that the lacrimal glands of beluga whales have similar histological and histochemical findings to those of artiodactyla and carnivora orders.
Topics: Animals; Beluga Whale; Coloring Agents; Diamines; Iron; Lacrimal Apparatus
PubMed: 34975225
DOI: No ID Found -
European Journal of Medicinal Chemistry Nov 2022N,6-Substituted 1,3,5-triazine-2,4-diamines (N-substituted guanamines) attracted significant interest due to their potential in the development of bioactive molecules.... (Review)
Review
N,6-Substituted 1,3,5-triazine-2,4-diamines (N-substituted guanamines) attracted significant interest due to their potential in the development of bioactive molecules. With just two points of diversity, this scaffold is proved to be suitable for constructing compounds targeting various enzymes, receptors, transporters, and nucleic acids with an array of therapeutic applications, particularly in cancer, inflammation, and CNS disorders. This review discusses progress in the synthesis of N,6-substituted 1,3,5-triazine-2,4-diamines and their biological activities ranging from the inhibition of cancer-related enzymes (e.g. DNA topoisomerase IIα, carbonic anhydrases, ubiquitin-conjugating enzyme 2B, lysophosphatidic acid acyltransferase β and various kinases) to the binding to CNS-relevant receptors (e.g. histamine H, serotonin 5-HT, adenosine A, and α7 nicotinic acetylcholine receptors).
Topics: Diamines; Triazines; alpha7 Nicotinic Acetylcholine Receptor
PubMed: 35981459
DOI: 10.1016/j.ejmech.2022.114645 -
The Annals of Occupational Hygiene Oct 2015Efficient, comfortable, yet affordable personal protective equipment (PPE) is needed to decrease the high incidence of allergic contact dermatitis arising from epoxy...
Efficient, comfortable, yet affordable personal protective equipment (PPE) is needed to decrease the high incidence of allergic contact dermatitis arising from epoxy resin systems (ERSs) in industrial countries. The aim of this study was to find affordable, user-friendly glove and clothing materials that provide adequate skin protection against splashes and during the short contact with ERS that often occurs before full cure. We studied the penetration of epoxy resin and diamine hardeners through 12 glove or clothing materials using a newly developed test method. The tests were carried out with two ERS test mixtures that had a high content of epoxy resin and frequently used diamine hardeners of different molar masses. A drop (50 µl) of test mixture was placed on the outer surface of the glove/clothing material, which had a piece of Fixomull tape or Harmony protection sheet attached to the inner surface as the collection medium. The test times were 10 and 30 min. The collecting material was removed after the test was finished and immersed into acetone. The amounts of diglycidyl ether of bisphenol A (DGEBA), isophorone diamine (IPDA), and m-xylylenediamine (XDA) in the acetone solution were determined by gas chromatography with mass spectrometric detection. The limit for acceptable penetration of XDA, IPDA, and DGEBA through glove materials was set at 2 µg cm(-2). Penetration through the glove materials was 1.4 µg cm(-2) or less. The three tested chemical protective gloves showed no detectable penetration (<0.5 µg cm(-2)). Several affordable glove and clothing materials were found to provide adequate protection during short contact with ERS, in the form of, for example, disposable gloves or clothing materials suitable for aprons and as additional protective layers on the most exposed parts of clothing, such as the front of the legs and thighs and under the forearms. Every ERS combination in use should be tested separately to find the best skin protection material, and this can be done by using this simple test method.
Topics: Dermatitis, Occupational; Diamines; Epoxy Resins; Gloves, Protective; Humans; Materials Testing; Occupational Exposure; Permeability
PubMed: 26130079
DOI: 10.1093/annhyg/mev040 -
Advances in Colloid and Interface... Jun 2022The highly selective chemical reaction of carbon dioxide with organic amines is considered to a mature technology and a feasible initial path for carbon capture. In... (Review)
Review
The highly selective chemical reaction of carbon dioxide with organic amines is considered to a mature technology and a feasible initial path for carbon capture. In order to solve the disadvantages of high volatility, equipment corrosion and high energy consumption of traditional organic amines, amine alcohol "mixture based" solution has been developed and showed excellent carbon dioxide absorption capacity, which is due to the positive effect of intermolecular interaction in amine alcohol "mixture based" solution system on thermodynamic properties. However, the influencing factors of the intermolecular force in multicomponent solution system are complex, including the chemical, physical, structural effects. Therefore, it is necessary to comprehensively use a variety of characterization methods to systematically understand the form of intermolecular interaction in multicomponent solution system. This review systematically discusses the determination of intermolecular interactions in diamine-diol multicomponent solutions by three mainstream research methods, theoretical calculation method, spectral method, and thermodynamic method, aiming to provide a theoretical reference for the industrial production, the supplement to experimental data, and construction and understanding of theoretical models of multicomponent solution system.
Topics: Amines; Carbon Dioxide; Diamines; Thermodynamics
PubMed: 35453067
DOI: 10.1016/j.cis.2022.102662 -
Scientific Reports Oct 2022Monitoring nicotinamide adenine dinucleotide (NADH) is important because NADH is involved in cellular redox reactions and cellular energy production. Currently, few...
Monitoring nicotinamide adenine dinucleotide (NADH) is important because NADH is involved in cellular redox reactions and cellular energy production. Currently, few biosensors quantify NADH in whole blood. However, they still have limitations due to several defects, including poor repeatability, long analysis time, and their requirement of extra sample pretreatment. In this study, we developed electrocatalytic sensors using screen-printed electrodes with a redox-active monolayer 4'-mercapto-N-phenylquinone diamine formed by a self-assembled monolayer of a 4-aminothiophenol (4-ATP). We exhibited their behavior as electrocatalysts toward the oxidation of NADH in whole blood. Finally, the electrocatalytic sensors maintained stability and exhibited 3.5 µM limit of detection, with 0.0076 ± 0.0006 µM/µA sensitivity in a mouse's whole blood. As proof of concept, a polyhexamethylene guanidine phosphate-treated mouse model was used to induce inflammatory and fibrotic responses, and NADH level was measured for 45 days. This work demonstrates the potential of electrocatalytic sensors to analyze NADH in whole blood and to be developed for extensive applications.
Topics: Adenosine Triphosphate; Animals; Biosensing Techniques; Diamines; Electrochemistry; Electrodes; Mice; NAD; Oxidation-Reduction
PubMed: 36202932
DOI: 10.1038/s41598-022-20995-x -
ChemistryOpen Jun 2022Studies have been performed aimed at the synthesis of N-heteroacenes via substitution reactions of 4,5-difluoro-1,2-dinitrobenzene with a diamine. The fluorine atoms are...
Studies have been performed aimed at the synthesis of N-heteroacenes via substitution reactions of 4,5-difluoro-1,2-dinitrobenzene with a diamine. The fluorine atoms are displaced first, followed by an activated nitro group. Two intermediates have been characterised by X-ray single-crystal structure determinations. Their intermolecular interactions were examined by Hirshfeld surfaces to assess their suitability for organic molecular electronics. The high reactivity of the phenazine, which is prone to oxidise and rearrange, as are displacement products prepared from it, is explained by the formation of a cis-aci-nitro form from the secondary amine of the phenazine and a nitro group.
Topics: Crystallography, X-Ray; Diamines; Fluorine; Molecular Structure; Phenazines
PubMed: 35674450
DOI: 10.1002/open.202200092 -
Journal of Medicinal Chemistry Apr 2016Antibiotic resistance is a growing threat to human health exacerbated by a lack of new antibiotics. We now describe a series of substituted diamines that produce rapid...
Antibiotic resistance is a growing threat to human health exacerbated by a lack of new antibiotics. We now describe a series of substituted diamines that produce rapid bactericidal activity against both Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus and stationary-phase bacteria. These compounds reduce biofilm formation and promote biofilm dispersal in Pseudomonas aeruginosa. The most potent analogue, 3 (1,13-bis{[(2,2-diphenyl)-1-ethyl]thioureido}-4,10-diazatridecane), primarily acts by depolarization of the cytoplasmic membrane and permeabilization of the bacterial outer membrane. Transmission electron microscopy confirmed that 3 disrupts membrane integrity rapidly. Compound 3 is also synergistic with kanamycin, demonstrated by the checkerboard method and by time-kill kinetic experiments. In human cell toxicity assays, 3 showed limited adverse effects against the HEK293T human kidney embryonic cells and A549 human adenocarcinoma cells. In addition, 3 produced no adverse effects on Caenorhabditis elegans development, survival, and reproduction. Collectively, diamines related to 3 represent a new class of broad-spectrum antibacterials against drug-resistant pathogens.
Topics: Animals; Anti-Bacterial Agents; Biofilms; Caenorhabditis elegans; Cell Membrane; Cell Membrane Permeability; Chemistry Techniques, Synthetic; Diamines; Drug Evaluation, Preclinical; Drug Interactions; Escherichia coli; HEK293 Cells; Humans; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Pseudomonas aeruginosa; Staphylococcus aureus
PubMed: 26964758
DOI: 10.1021/acs.jmedchem.5b01912 -
Bioscience, Biotechnology, and... Jul 2022The aromatic diamine 2-(4-aminophenyl)ethylamine (4APEA) is a potential monomer for polymers and advanced materials. Here, 4APEA was produced by fermentation using...
The aromatic diamine 2-(4-aminophenyl)ethylamine (4APEA) is a potential monomer for polymers and advanced materials. Here, 4APEA was produced by fermentation using genetically engineered Escherichia coli (Masuo et al.2016). Optimizing fed-batch cultures of this strain produced the highest reported yield to date of 4APEA (7.2%; 3.5 g/L versus glucose) within 72 h. Appropriate aeration was important to maximize production and avoid unfavorable 4APEA degradation. Fermented 4APEA was purified from culture medium and polymerized with methylene diphenyldiisocyanate and hexamethylene diisocyanate to produce polyureas PU-1 and PU-2, respectively. The decomposition temperatures for 10% weight loss (Td10) of PU-1 and PU-2 were 276 °C and 302 °C, respectively, and were comparable with that of other thermostable aromatic polyureas. This study is the first to synthesize polyureas from the microbial aromatic diamine. Their excellent thermostability will be useful for the industrial production of heat-resistant polymer materials.
Topics: Diamines; Escherichia coli; Fermentation; Glucose; Hot Temperature; Metabolic Engineering; Phenethylamines
PubMed: 35612977
DOI: 10.1093/bbb/zbac077