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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 -
Journal of Food Protection Sep 2021Essential foods as part of a daily meal may include numerous kinds of biogenic amines (BAs) at various concentrations. BAs have a variety of toxicological effects on... (Review)
Review
ABSTRACT
Essential foods as part of a daily meal may include numerous kinds of biogenic amines (BAs) at various concentrations. BAs have a variety of toxicological effects on human health and have been linked to multiple outbreaks of foodborne disease. BAs also are known to cause cancer based on their ability to react with nitrite salts, resulting in the production of carcinogenic organic compounds (nitrosamines). Ingestion of large quantities of BAs in food causes toxicological effects and health disorders, including psychoactive, vasoactive, and hypertensive effects and respiratory, gastrointestinal, cardiovascular, and neurological disorders. The toxicity of BAs is linked closely to the BAs histamine and tyramine. Other amines, such as phenylethylamine, putrescine, and cadaverine, are important because they can increase the negative effects of histamine. The key method for reducing BA concentrations and thus foodborne illness is management of the bacterial load in foods. Basic good handling and hygiene practices should be used to control the formation of histamine and other BAs and reduce the toxicity histamine and tyramine. A better understanding of BAs is essential to enhance food safety and quality. This review also includes a discussion of the public health implications of BAs in foods.
Topics: Biogenic Amines; Cadaverine; Food Contamination; Histamine; Humans; Putrescine; Tyramine
PubMed: 34375430
DOI: 10.4315/JFP-21-047 -
Journal of the American Chemical Society Dec 2019The enantioselective, vicinal diamination of alkenes represents one of the stereocontrolled additions that remains an outstanding challenge in organic synthesis. A...
The enantioselective, vicinal diamination of alkenes represents one of the stereocontrolled additions that remains an outstanding challenge in organic synthesis. A general solution to this problem would enable the efficient and selective preparation of widely useful, enantioenriched diamines for applications in medicinal chemistry and catalysis. In this article, we describe the first enantioselective, diamination of simple alkenes mediated by a chiral, enantioenriched organoselenium catalyst together with a bistosyl urea as the bifunctional nucleophile and fluorocollidinium tetrafluoroborate as the stoichiometric oxidant. Diaryl, aryl-alkyl, and alkyl-alkyl olefins bearing a variety of substituents are all diaminated in consistently high enantioselectivities but variable yields. The reaction likely proceeds through a Se(II)/Se(IV) redox catalytic cycle reminiscent of the dichlorination reported previously. Furthermore, the -stereospecificity of the transformation shows promise for highly enantioselective diaminations of alkenes with no strong steric or electronic bias.
Topics: Alkenes; Amination; Catalysis; Diamines; Organoselenium Compounds; Oxidants; Oxidation-Reduction; Stereoisomerism; Urea
PubMed: 31742399
DOI: 10.1021/jacs.9b11261 -
Nature Communications Oct 2019The 1,2-diamine motif is widely present in natural products, pharmaceutical compounds, and catalysts used in asymmetric synthesis. The simultaneous introduction of two...
The 1,2-diamine motif is widely present in natural products, pharmaceutical compounds, and catalysts used in asymmetric synthesis. The simultaneous introduction of two amino groups across an alkene feedstock is an appealing yet challenging approach for the synthesis of 1,2-diamines, primarily due to the inhibitory effect of the diamine products to transition metal catalysts and the difficulty in controlling reaction diastereoselectivity and regioselectivity. Herein we report a scalable electrocatalytic 1,2-diamination reaction that can be used to convert stable, easily available aryl alkenes and sulfamides to 1,2-diamines with excellent diastereoselectivity. Monosubstituted sulfamides react in a regioselective manner to afford 1,2-diamines bearing different substituents on the two amino groups. The combination of an organic redox catalyst and electricity not only obviates the use of any transition metal catalyst and oxidizing reagent, but also ensures broad reaction compatibility with a variety of electronically and sterically diverse substrates.
PubMed: 31672991
DOI: 10.1038/s41467-019-13024-5 -
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 -
Environmental Science & Technology Oct 2023-(1,3-Dimethylbutyl)-'-phenyl--phenylenediamine (6-PPD) is a widely used antioxidant in tire rubber known to enter the aquatic environment via road runoff. The...
-(1,3-Dimethylbutyl)-'-phenyl--phenylenediamine (6-PPD) is a widely used antioxidant in tire rubber known to enter the aquatic environment via road runoff. The associated transformation product (TP) 6-PPD quinone (6-PPDQ) causes extreme acute toxicity in some fish species (e.g., coho salmon). To interpret the species-specific toxicity, information about biotransformation products of 6-PPDQ would be relevant. This study investigated toxicokinetics of 6-PPD and 6-PPDQ in the zebrafish embryo (ZFE) model. Over 96 h of exposure, 6-PPD and 6-PPDQ accumulated in the ZFE with concentration factors ranging from 140 to 2500 for 6-PPD and 70 to 220 for 6-PPDQ. A total of 22 TPs of 6-PPD and 12 TPs of 6-PPDQ were tentatively identified using liquid chromatography coupled to high-resolution mass spectrometry. After 96 h of exposure to 6-PPD, the TPs of 6-PPD comprised 47% of the total peak area (TPA), with 4-hydroxydiphenylamine being the most prominent in the ZFE. Upon 6-PPDQ exposure, >95% of 6-PPDQ taken up in the ZFE was biotransformed, with 6-PPDQ + O + glucuronide dominating (>80% of the TPA). Among other TPs of 6-PPD, a reactive -phenyl--benzoquinone imine was found. The knowledge of TPs of 6-PPD and 6-PPDQ from this study may support biotransformation studies in other organisms.
Topics: Animals; Biotransformation; Chromatography, Liquid; Rubber; Zebrafish; Embryo, Nonmammalian; Toxicokinetics; Phenylenediamines; Benzoquinones
PubMed: 37782849
DOI: 10.1021/acs.est.3c02819 -
American Journal of Rhinology & Allergy Nov 2023COVID-19 has been associated with olfactory dysfunction in many infected patients. The rise of calcium levels in the nasal secretions plays an essential role in the... (Randomized Controlled Trial)
Randomized Controlled Trial
BACKGROUND
COVID-19 has been associated with olfactory dysfunction in many infected patients. The rise of calcium levels in the nasal secretions plays an essential role in the olfaction process with a desensitization effect on the olfactory receptor neurons and a negative impact on the olfaction transmission. Ethylene diamine tetra acetic acid (EDTA) is a chelating agent that can bind free calcium in the nasal secretions, thereby reducing the adverse effects of calcium on olfactory function.
OBJECTIVES
The objective of this work is to demonstrate the effect of intranasal EDTA on improving olfactory dysfunction following COVID-19.
METHODS
Fifty patients with a history of COVID-19 and olfactory dysfunction that persisted for more than 6 months were enrolled in the current prospective randomized clinical trial. Participants were randomized into 2 equal groups. Twenty-five patients were treated with olfactory training only, while the remaining 25 patients received treatment with olfactory training and a topical nasal spray of ethylene diamine tetra acetic acid. The olfactory function was assessed before treatment and 3 months later using the Sniffin' Sticks test. Additionally, the determination of calcium level in the nasal secretions was performed using an ion-selective electrode before treatment and 3 months later.
RESULTS
Eighty-eight percent of the patients treated with olfactory training in addition to EDTA exhibited clinical improvement, while 60% showed improvement in patients treated with olfactory training only. Furthermore, a significant decrease in the measured calcium level in the nasal secretions was demonstrated after the use of ethylene diamine tetra compared to patients treated with olfactory training only.
CONCLUSION
Ethylene diamine tetra acetic acid may be associated with an improvement of the olfactory function post-COVID-19.
Topics: Humans; Smell; Olfaction Disorders; Acetic Acid; Calcium; Edetic Acid; COVID-19; Ethylenes
PubMed: 37786364
DOI: 10.1177/19458924231184055 -
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 -
International Journal of Environmental... Jun 2022This systematic review aimed to compare the efficacy of herbal agents with ethylene diamine tetraacetic acid (EDTA) in removing the smear layer during root canal... (Review)
Review
This systematic review aimed to compare the efficacy of herbal agents with ethylene diamine tetraacetic acid (EDTA) in removing the smear layer during root canal instrumentation. The research question in the present study was to assess: "Is there a significant difference in reducing smear layer comparing EDTA and herbal agents?" Electronic databases (PubMed, Scopus, and Web of Science) were searched from their start dates to April 2022 using strict inclusion and exclusion criteria, and reviewed following PRISMA (Preferred Reporting Items for Systematic Reviews and Meta-Analyses) 2020 guidelines. Only in vitro studies comparing herbal agents with EDTA were included in the current systematic review. Two reviewers independently assessed the included articles. A total of 625 articles were obtained from an electronic database. Eighteen papers were included for review of the full text, out of which, ten papers were excluded because they did not meet the inclusion criteria. Finally, eight articles were included in the systematic review. The present systematic review considered only in vitro studies; hence, the result cannot be completely translated to strict clinical conditions. The results of the present systematic review have shown that extract, and neem show better smear layer removal compared to other herbal agents, whereas they showed reduced smear layer removal when compared with EDTA. Although, it was seen that most of the included studies did not report a high quality of evidence. Hence, the present systematic review concludes that herbal agents have reported to show inferior smear layer removal when compared to EDTA. Thus, as far as herbal based alternatives are concerned, there is no highest level of evidence to state its real benefit when used as a chelating root canal irrigant.
Topics: Acetic Acid; Chelating Agents; Edetic Acid; Ethylenes; Humans; Microscopy, Electron, Scanning; Root Canal Preparation; Smear Layer; Sodium Hypochlorite
PubMed: 35682452
DOI: 10.3390/ijerph19116870