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Search results for: HETEROCYCLIC AROMATIC AMINES
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Approaches Towards Better Immunosuppressive Agents
PublicationSeveral classes of compounds are applied in clinics due to their immunosuppressive properties in transplantology and the treatment of autoimmune diseases. Derivatives of mycophe-nolic acid, corticosteroids and chemotherapeutics bearing heterocyclic moieties like methotrexate, azathioprine, mizoribine, and ruxolitinib are active substances with investigated mechanisms of action. However, improved synthetic approaches of known drugs...
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Dissociative photo-double-ionization of the isoxazole molecules
PublicationThe five-membered heterocyclic rings are incorporated into a wide variety of structures that play a vital role in many biochemical processes. In particular, the isoxazole molecule appears in many bioactive compounds due to its unique ring structure that consists of one oxygen atom and one nitrogen atom at adjacent positions. The unique atomic composition and bond arrangement of isoxazole imply its specific electronic properties...
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Structural Factors Affecting Cytotoxic Activity of (E)-1-(Benzo[d ][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives
PublicationDerivatives of (E)-1-(5-alkoxybenzo[d][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one (1) demonstrated exceptionally high in vitro cytotoxic activity, with IC50 values of the most active derivatives in the nanomolar range. To identify structural fragments necessary for the activity, several analogs deprived of selected fragments were prepared, and their cytotoxic activity was tested. It was found that the activity depends on combined effects...
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Hopping or Tunneling? Tailoring the Electron Transport Mechanisms through Hydrogen Bonding Geometry in the Boron-Doped Diamond Molecular Junctions
PublicationMechanisms of charge transport in molecular junctions involving hydrogen bonds are complex and remain mostly unclear. This study is focused on the elucidation of the electron transfer in a molecular device consisting of two boron-doped diamond interfaces bound with an aromatic linker and a hydrogen bonding surrogating molecule. The projected local density of states (PLODS) analysis coupled with transmission spectra and current−voltage...
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Practical Method for the Preparation of 2,2-Dimethyl-5- {aryl[(hetero)aryl]methyl}-1,3-dioxane-4,6-diones: Synthesis and Mechanistic Study
PublicationAn efficient practical synthetic procedure has been developed for the synthesis of 2,2-dimethyl-5-{aryl[(hetero)aryl]methyl}- 1,3-dioxane-4,6-diones through Friedel–Crafts alkylation. The scope and limitation of the reaction of 2,2-dimethyl-5-arylidene-1,3-dioxane- 4,6-diones with π-excess aromatic systems have been delineated.
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Enhancement of PUR/PIR foam thermal stability after addition of Zostera marina biomass component investigated via thermal analysis and isoconversional kinetics
PublicationIn the present work, a thorough thermogravimetric (TG) analysis of bio-based polyurethane–polyisocyanurate (PUR–PIR) foams in both nitrogen and oxygen atmosphere is performed. A sustainable element of the foam is a biopolyol obtained via acid-catalyzed liquefaction of Zostera marina and Enteromorpha Algae biomass. Based on isoconversional analysis and apparent activation energies, several conclusions are obtained. In contradiction...
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Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery
PublicationAbstract: Five-membered 1,2,4-oxadiazole heterocyclic ring has received considerable attention because of its unique bioisosteric properties and an unusually wide spectrum of biological activities. Thus, it is a perfect framework for the novel drug development. After a century since the 1,2,4-oxadiazole have been discovered, the uncommon potential attracted medicinal chemists’ attention, leading to the discovery of a few presently...
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Heteroleptic tri-tert-butoxysilanethiolate complexes of manganese(II) - thermal studies
PublicationThe thermal behavior of Mn(II) silanethiolate series [Mn(SR)2L(MeOH)n], where R=SSi(OBut)3, L=heterocyclic nitrogen base and n=0, 1 or 2 has been comparatively investigated using differential scanning calorimetry (DSC), thermogravimetry (TG) and TG-infrared spectoscopy (IR) techniques. The TG curves indicate the differences in the thermal decomposition due to presence of distinct N-donor ligands and labile MeOH molecules coordinated...
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Exploring the cocrystallization potential of urea and benzamide
PublicationThe cocrystallization landscape of benzamide and urea interacting with aliphatic and aromatic carboxylic acids was studied both experimentally and theoretically. Ten new cocrystals of benzamide were synthesized using an oriented samples approach via a fast dropped evaporation technique. Information about types of known bi-component cocrystals augmented with knowledge of simple binary eutectic mixtures was used for the analysis...
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Synthesis of new antrapyridazone derivatives - a novel group of anticancer agents active on a multidrugresistant(MDR) tumor cell lines
PublicationNovel antrapyridazone derivatives were synthesized and biologically evaluated in order tobroaden the data on structure-activity relationship of this class of cytostatics. Recent literaturedata prove that acetamides react better with aryl chlorides. A new approach based onintroduction of other amides form into aromatic ring in Ullmann was tested. This new methodcould give better yields and make purification step more convenient.
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Synthesis and crystal structure of ferrocenyl benzothiazole derivatives
PublicationNovel ferrocenyl-containing benzothiazole derivatives were synthesised in moderate yields by one-pot α-amidoalkylation of ferrocene. The reaction conditions were critically evaluated and the crystal structure of one of the amidoalkylated ferrocenes was resolved. Oxidation of the obtained compounds led to known fully aromatic 2-ferrocenylbenzothiazole in 81 % yield, which represents a convenient alternative to earlier methods utilizing...
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Detection and removal of priority substances and emerging pollutants from stormwater: case study of the Kołobrzeska collector, Gdańsk, Poland
PublicationProgressive urban development affects environmental balance and disrupts the hydrologic cycle, in which rainfall plays a significant role. Since rainwater is considered a valuable resource of the environment, many technical solutions are implemented that enable effective rainwater management. On the other hand, stormwater runoff from urban areas contains numerous (also toxic) substances, and therefore should be properly treated....
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Polychlorinated biphenyls (PCBs) in bottom sediments: Identification of sources
PublicationPolychlorinated biphenyls (PCBs) can enter the environment from various sources. They are synthetic chemicals and as such are present in the environment mainly as mixtures containing various amounts of PCB congeners. It is therefore difficult to pinpoint the source of PCB emissions into the environment and the pathways along which they migrate there. The situation is different where locating the emission sources of polycyclic aromatic...
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Saccharides
PublicationSaccharides are widely distributed in nature as the major component of fruits and vegetables (primarily monosaccharides), milk and malt (mainly disaccharides), and grains (mostly polysaccharides). They are an important source of energy, structural material, as well as flavor and taste factors. Molecules of this class of compounds contain mainly carbon, hydrogen, and oxygen atoms; however, most natural saccha- rides do not have...
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Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties
PublicationGlucosamine-6-phosphate synthase (GlcN-6-P synthase) is known as a promising target for antimicrobial agents and antidiabetics. Several compounds of natural or synthetic origin have been identified as inhibitors of this enzyme. This set comprises highly selective L-glutamine, amino sugar phosphate or transition state intermediate cis-enolamine analogues. Relatively low antimicrobial activity of these inhibitors, poorly penetrating...
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Polyurethane-based aerogels: Preparation, properties, and applications
PublicationPolyurethane aerogels (PUAs) are interesting materials because of their high porosity, low density, and low thermal conductivity, which result in their application as thermal insulations. PUAs are mainly synthesized using di- and polyisocyanates, diols or polyols, catalysts (tertiary amines and organometallic), and solvents (which are used as reaction medium, purifying of obtained semiproducts). Preparation procedure involves several...
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Multi-Decision Analysis for selection of the best procedure for PAHs determination in smoked food.
PublicationMaking a proper decision in multifacitated situation is very challenging task. Especially, if there are many alternatives and criteria, even contradictory ones. The support tools may be application of MultiCriteria Decision Analysis methods. In this study the application of PROMETHEE...
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Occurrence of specific pollutants in a mixture of sewage and rainwater from an urbanized area
PublicationUrban runoff appears to be a pathway for transferring new emerging pollutants from land-based sources to the aquatic environment. This paper aimed to identify and describe the groups of pollutants present in rainwater surface runoff as well as their mixture with wastewater in the combined sewer system from urbanized catchments and to determine the correlations between these pollutants. Four leading groups of new emerging pollutants...
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Azo and azoxythiacrown ethers: synthesis and properties
PublicationA series of 16- and 18-membered azo- and azoxythiacrown ethers have been synthesized by reductive macrocyclization of the respective bis(nitrophenoxy)oxaalkanes. The aromatic residues located in the polyether region of the molecule were introduced to macrocyclic skeletons and their affinities toward different groups of metal cations in ion-selective electrodes were described. X-ray structures for one dinitropodand and one azoxybenzothiacrown...
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Novel and Efficient Synthesis of Unsymmetrical Trisulfides
PublicationWe have developed a convenient method for the synthesis of unsymmetrical trisulfides under mild conditions in very good yields. The designed method is based on the straightforward preparation of 1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane, sulfur dichloride (SCl2) and dodecane-1-thiol. The unsymmetrical trisulfides can...
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Hybrid biobateryy based on arylated carbon nanotubes and laccase
PublicationSingle-walled carbon nanotubes (SWCNT) were covalently modified with antracene and antraquinone and used for the construction of cathodes for biocatalytic reduction od dioxygen. The nanotubes with aromatic groups casted onto the electrode increased the working surface of the electrode and enabled efficient direct electron tarnsfer (DET) between the enzyme and the electrode. the aryl groups enter the hydrophobic pocket of the T1...
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Materials for Mediator-free Electron Transfer in the Enzymatic Electrodes of Biobatteries and Biofuel Cells
PublicationWe present functionalization of single-walled carbon nanotubes (SWCNTs) and their application in the enzymatic fuel cells construction. SWCNTs were covalently modified with different types of aromatic moieties. Free radical reaction was employed to create direct carbon-carbon bond between moiety and SWCNTs. In second approach functionalization takes place through amide bonding. Functionalized SWCNTs were characterized by spectroscopy...
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Development of novel smartphone-based methods of wine quality assessment
PublicationThe doctoral dissertation concerns the development of novel smartphone-based analytical methods of wine quality evaluation, which would be in line with the stipulations of green and equitable analytical chemistry. This solution is based on the analysis of biogenic amines and selected bioactive compounds. The dissertation is based on four articles containing the results of research which led to the development of smartphone-based...
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Crystal structures of aminotransferases Aro8 and Aro9 from Candida albicans and structural insights into their properties
PublicationAminotransferases catalyze reversibly the transamination reaction by a ping-pong bi-bi mechanism with pyridoxal 5′-phosphate (PLP) as a cofactor. Various aminotransferases acting on a range of substrates have been reported. Aromatic transaminases are able to catalyze the transamination reaction with both aromatic and acidic substrates. Two aminotransferases from C. albicans, Aro8p and Aro9p, have been identified recently, exhibiting...
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Perspektywy wykorzystania olfaktometrii i elektronicznego nosa w badaniach stanu środowiska
PublicationIn environmental state investigations the two approaches are dominate: field olfactometry and instrumental methods. In contradiction to classical chromatographic methods, both field olfactometry and electronic nose (e-nose) in based on the analysis of the aroma as a whole, without separating gaseous mixture (air) to individual aromatic compounds. With respect to simplicity of use and relatively short time of analysis, both systems...
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Novel and Efficient Methods for the Synthesis of Symmetrical Trisulfides
PublicationWe have developed a convenient methods for the synthesis of symmetrical trisulfides under mild conditions in very good yields. The described methods are based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinane-2-disulfanyl derivatives from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The symmetrical...
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TBAF Promoted Formation of Symmetrical Trisulfides
PublicationWe have developed a new method for the synthesis of functionalized symmetrical trisulfides based on (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorin-2-yl)disulfanyl derivatives prepared from readily available 5,5-dimethyl-2-sul-fanyl-2-thioxo-1,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The symmetrical trisulfides can be obtained from aliphatic and aromatic thiols andL-cysteine derivatives...
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Synthesis of functionalized new conjugates of batracylin with tuftsin/ retro-tuftsin derivatives and their biological evaluation
PublicationNew batracylin conjugates with tuftsin/retro-tuftsin derivatives were designed and synthesized using T3P as a coupling agent. The conjugates possess an amide bond formed between the carboxyl group of heterocyclic molecule and the N-termini of the tuftsin/retro-tuftsin chain. The in vitro cytotoxic activity of the new analogues and their precursors was evaluated using a series of human and murine tumor cells. BAT conjugates containing...
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Chromatographic behavior of a new hybrid type RP material containing silica bonded 1,3-alternate 25,27-bis-[cyanopropyloxy]-26,28-bis-[3-propyloxy]-calix[4]arene
PublicationA novel 1,3-alternate 25,27-bis-[cyanopropyloxy]-26,28-bis-[3-propyloxy]-calix[4]arene-bonded silica gel stationary phase (CalixPrCN) was prepared and it's structure was confirmed by ATR-FTIR spectroscopy and elemental analysis. The CalixPrCN phase was characterized in terms of their surface coverage, hydrophobic selectivity, aromatic selectivity, shape selectivity, hydrogen bonding capacity, residue metal content, and silanol...
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Preparation and X-ray structures of selected aminium thiosulfates
PublicationVarious types of aminium thiosulfates (1–6), including hydrates and mixed salts, have been obtained by the reaction of ammonium thiosulfate with amines. Tertbutylamine, cyclo-hexylamine and 1,6-diaminohexane gave crystals of (t-BuNH3)2S2O3·H2O (1), (c-C6H11NH3)2S2O3 (3) and {(NH4)2(H3NC6H12NH3)(S2O3)2} (6), respectively, which were investigated by X-ray structural analysis. Extensive hydrogen bonding of the N-H…O and N-H…S type...
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Simple smartphone-based methods for the determination of bioactive compounds in wine
PublicationA set of simple smartphone-based methods of bioactive compounds determination were developed for wine analysis. Procedures for smartphone-based determination of the total content of phenolic compounds, flavonoids, anthocyanins and biogenic amines, as well as measurement of antioxidant activity were developed and fully validated. The experimental setup is based on smartphone and 3D-printed device, though it is very simple and can...
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A versatile and convenient preparation of unsymmetrical diaryl disulfides
PublicationWe have developed a convenient method for the synthesis of unsymmetrical diaryl disulfides under mild conditions in excellent yields. The described method is based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinane-2-sulfenyl bromide from readily available 5,5-dimethyl-2-thiolo-2-thioxo-1,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The unsymmetrical...
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The structure, including stereochemistry, of levorin A1
PublicationThe constitution and stereostructure of levorin A1 1, an aromatic heptaeneantifungal antibiotic, was established on the basis of NMR studies, which contained DQFCOSY,ROESY, HSQC and HMBC experiments. Mycosamine moiety was used as an internalchiral probe to determine the absolute configuration of levorin A1 stereogenic centers: 13S,15R, 17S, 18R, 19S, 21R. The relative configuration of the remaining stereogenic centers wasassigned...
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Funcionality assessment of Citrus Hysteria peel as a protective barrier using gas chromatography
PublicationThe aim of this study was to analyse the volatile fractions of fruit peel and pulp using two-dimensional gas chromatography technique coupled with mass spectrometry. The isolation of the compounds was achieved by microextraction to the stationary phase from the headspace of the sample (HS-SPME). Mass spectrometry with time-of-flight analyser (TOF-MS) was used to identify the chemical compounds. There are no reports in the literature...
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Functionalized azobenzocrown ethers as sensor materials—The synthesis and ion binding properties
PublicationNew 13- and 16-membered azobenzocrown ethers with aromatic amino, amide, ether–ester or ether–amide residue in para position to an azo moiety were obtained. Acid–base properties and ion binding ability of the colored compounds were studied by spectroscopic methods: UV–vis, fluorimetry and 1H NMR spectroscopy. Selected azobenzocrowns were tested as ionophores in ion-selective membrane electrodes (ISEs) – classic and miniature all...
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Solid Phase Synthesis and Biological Activity of Tuftsin Conjugates
PublicationNew tuftsin/retro-tuftsin conjugates were designed and synthesized using a classical fluorenylmethoxycarbonyl (Fmoc) solid phase procedure. All the peptide conjugates were divided into three series: 1,4-dihydroxyanthraquinone (type A), 1-nitroacridine (type B), and 4-carboxyacridone (type C) derivatives. In type A conjugates, the N-terminal group of the peptide chain is directly connected to the anthraquinone ring at C1 (Scheme...
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Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles in the Presence of Heterogeneous Catalyst
PublicationTetrazoles are five-membered heterocyclic compounds containing in their rings four nitrogen atoms. They have wide applications as corrosion inhibitors, analytical reagents, high-energy materials and gas generating compositions. Tetrazoles also play important role in coordination chemistry as ligands and in medicinal chemistry as metabolically stable surrogates for carboxylic acids. In recent years, investigation of new method of...
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Molecular modeling and evaluation of novel dibenzopyrrole derivatives as telomerase inhibitors and potential drug for cancer therapy
PublicationDuring previous years, many studies on synthesis, as well as on anti-tumor, anti-inflammatory and anti-bacterial activities of the pyrazole derivatives have been described. Certain pyrazole derivatives exhibit important pharmacological activities and have proved to be useful template in drug research. Considering importance of pyrazole template, in current work the series of novel inhibitors were designed by replacing central...
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Chromogeniczne pochodne azoli jako składniki warstw receptorowych czujników optycznych
PublicationGłównym celem badań prowadzonych w ramach studium doktoranckiego była synteza oraz badanie właściwości chromogenicznych pochodnych azoli, makrocyklicznych i acyklicznych, jako składników warstw receptorowych czujników optycznych. Otrzymane związki zawierają w swojej strukturze resztę heterocykliczną – azol, który może uczestniczyć w tworzeniu kompleksów z jonami metali ciężkich oraz co najmniej jedno ugrupowanie azowe. Obecność...
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Botanical and geographical origin characterization of polish honeys by headspace SPME-GCxGC-TOFMS
PublicationVolatile organic compounds (VOCs) composition of Polish honeys obtained from various geographical regions was studied. Headspace solid phase microextraction (HS-SPME) using Divinylbenzene/Carboxen/Polydimethylsiloxane-coated fibers was used in combination with comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GC× GC-TOFMS) because of the complexity of the samples. Acacia, linden, rapeseed, buckwheat...
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The New Test Procedure for Group-Type Composition of Base Oils of Lubricating Oils, Especially Emitted into the Environment
PublicationMineral base oil, a product of multistep fine refining of the relevant fractions from vacuum distillation of crude oil, is a main component of so-called mineral lubricating oils containing aliphatic and alicyclic substituted aromatic hydrocarbons, i.e., derivatives of benzene and biphenyl. Mineral lubricating oil is composed mostly of mineral base oil and a low amount of enriching additives, most often products of advanced organic...
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Synthesis and antimicrobial activity of amino acid and peptide derivatives of mycophenolic acid
PublicationThe series of 16 novel amino acid and peptide mycophenolic acid (MPA) derivatives was obtained as potential antibacterial agents. Coupling of MPA with respective amines was optimized with condensing reagents such as EDCI/DMAP and T3P/TEA. Amino acid analogs were received both as methyl esters and also with the free carboxylic group. The biological activity of the products was tested on five references bacterial strains: Klebsiella...
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Direct determination of cadaverine in the volatile fraction of aerobically stored chicken breast samples
PublicationTo supplement the currently used methods for poultry meat shelf life assessment, it might be necessary to develop a technique for rapid headspace analysis of volatiles with no prior sample preparation step. Biogenic amines, in particular cadaverine, are considered meat spoilage indicators. Described in this article are the results of a preliminary investigation of the applicability of proton transfer reaction mass spectrometry...
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Cure kinetics of epoxy/MWCNTs nanocomposites: Isothermal calorimetric and rheological analyses
PublicationA combinatorial route has been applied in cure kinetics study of epoxy nanocomposites containing multi-walled carbon nanotubes (MWCNTs) based on differential scanning calorimetry and rheokinetic analyses under isothermal conditions. Pristine and amine-modified MWCNTs bearing primary and secondary amines were used at very low concentrations (0.1 and 0.3 wt.% based on epoxy weight). Model-free and model-fitting methods were applied...
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Monitoring and efficiency assessment of biofilter air deodorization using electronic nose prototype
PublicationBiofiltration is one of the techniques used to reduce odorants in the air. It is based on the aerobic degradation of pollutants by microorganisms located in the filter bed. The research presents the possibility of using the electronic nose prototype for monitoring and efficiency assessment of air biofiltration. The study was conducted using model gas mixtures containing representatives of three groups of chemical compounds: n-hexane...
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Selected symmetrically substituted carbazoles: Investigation of anticancer activity and mechanisms of action at the cellular and molecular levels
PublicationDNA topoisomerases play a critical role as essential enzymes in controlling alterations in the topology of DNA. They achieve this by orchestrating the coordinated process of breaking and rejoining DNA strands, which is crucial for maintaining the proper structure of DNA during regular cellular development. The search for and development of new potential anticancer drugs is a challenging yet immensely important area of research...
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Characterization of 1,3-alternate calix[4]arene-silica bonded stationary phases and their comparison to selected commercial columns by using principal component analysis
PublicationTwelve calix[4]arene stationary phases in 1,3-alternate conformation, synthesized in the authors laboratory, were characterized in terms of their surface coverage, hydrophobic selectivity, aromatic selectivity, shape selectivity, hydrogen bonding capacity and ion-exchange capacity. The set of tests commonly used for evaluation of commercially available stationary phases was applied to assess fundamental chromatographic properties...
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Analysis of MArkers of Exposure to Constituents of Environmental Tobacco Smoke (ETS)
PublicationTobacco smoke is a complex mixture of more than 4000 chemical compounds, many of which are harmful to human health. These compounds belong to various chemical classes, including amides, imides, lactams, carboxylic acids, aldehydes, ketones, alcohols, phenols, amines, hydrocarbons, ethers, and inorganic compounds. There are three types of tobacco smoke streams: the mainstream, the sidestream, and environmental tobacco smoke (ETS)....
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Unusual behavior of secondary amine group as a leaving group
PublicationIn our recent project we focused on reactivity of2,2-dimethyl-4,6-dioxane-1,3-dione carbamoilo- and thiocarbamoylo- derivatives as a ketenesource. Meldrum`s acid derivatives after thermal decomposition gives substituted keteneswith stoichiometric yield, that can be trapped with various spectrum of nucleophiles likealcohols, thiols, amine, imines etc. In case of5-[3-(dimethylamino)-sulfanyl-propyliden]-2,2-dimethyl-1,3-dioxane-4,6-dione...
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Chromatographic lipophilicity determination using large volume injections of the solvents non-miscible with the mobile phase
PublicationA new perspective in the lipophilicity evaluation through RP-HPLC is permitted by analysis of the retentionfactor (k) obtained by injecting large volumes of test samples prepared in solvents immiscible withmobile phase. The experiment is carried out on representative groups of compounds with increasedtoxicity (mycotoxins and alkaloids) and amines with important biological activity (naturally occurringmonoamine compounds and related...