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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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Preparation of Pseudopeptides Building Blocks with Retro-Thioamide Bond Mediated via Thiocarbamoyl Meldrum's Acid
PublicationAn easy and efficient synthesis of pseudo tripeptide containing a thiomalonamide moiety was developed. Isothiocyanate derivatives of amino acids react smoothly with 2,2-dimethyl-1,3-dioxane-4,6-dione yielding new thiocarbamoyl Meldrum's acids. Thermal decomposition of this new Meldrum's acid derivatives generate thiocarbamoyl ketenes, which acylate amino acid esters to give pseudo tripeptides.
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Development of Safirinium dyes for new applications: fluorescent staining of bacteria, human kidney cells, and the horny layer of the epidermis
PublicationLow-molecular synthetic fluorophores are convenient tools in bioimaging applications. Several derivatives of Safirinium dyes as well as their reactive N-hydroxysuccinimide (NHS) esters bearing diverse substituents were synthesized and evaluated experimentally in terms of their lipophilicity by means of reverse-phase and immobilized artificial membrane high-performance liquid chromatography. Subsequently, the selected compounds...
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Mechanism of selective anticancer activity of isothiocyanates relies on differences in DNA damage repair between cancer and healthy cells
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Alkanethiolates of Group 1,2, and 13-15 Metals
PublicationThis manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of alkanethiolates of group 1, 2, and 13-15 metals. Alkanethiolates can be converted into S-alkyl thiocarboxylic acid esters, 1-thioglycosides, S-alkyl thiosulfinates, tetrahydro-1,4-thiazine-3-ones, sulfides, disulfides, sulfonium salts, dithioacetals and dithioketals, etc. These transformations are accomplished by...
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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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Greener organic solvents in analytical chemistry
PublicationThe paper presents the most recent advances in analytical applications of greener organic solvents. Substitution of problematic solvents with more benign organic ones is much easier than shifting to technique applying alternative solvents, such as ionic liquids or supercritical fluids. In the area of liquid chromatography greener mobile phases, much attention is given to application ethanol or acetone instead of acetonitrile. Solvent-based...
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Synthesis and biological activity of mycophenolic acid-amino acid derivatives
PublicationIn search of new immunosuppressants, mycophenolic acid (MPA) was coupled with amino acid methyl esters followed by hydrolysis to analogs bearing free carboxylic groups. The obtained compunds were tested in vitro as growth inhibitors of lymphoid cell line (Jurkat) and human peripheral blood mononuclear cells (PBMC) from healthy donors. According to obtained results recovering of free carboxylic group increased their activity. Additionally,...
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Extensive Drug Resistance of Strong Biofilm-Producing Acinetobacter baumannii Strains Isolated from Infections and Colonization Hospitalized Patients in Southern Poland
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Transition-Metal-Promoted Oxidative Cyclization To Give 1,2,4-Trisubstituted Carbazole Scaffolds
PublicationHerein, we describe the synthesis of a 1,2,4-trisubstituted carbazole core from 5-(1H-indol-3-yl)-3-oxopentanoic acid esters or amides. For oxidative cyclization, we tested two different approaches. First, we used manganese triacetate as a conventional moderate oxidizer to ensure the radical course of the reaction. Second, we examined the use of a more complex oxidizing agent I2/Me(OTf)3. In both cases, formation of a fused-ring...
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Rapeseed oil methyl ester production in an individual household
PublicationFatty acid methyl esters, commonly known as biodiesel, are a cheap and environmental-friendly fuel substitute for diesel engines. Aside from industrial production, individual biodiesel manufacturing is also and important method of fulfilling the requirements of EU Parliament directive no. 2003/30/WE about supporting the use of renewable fuels in transport. Individual FAME production guarantees easy access to the main raw material...
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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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Anticancer Properties of Amino Acid and Peptide Derivatives of Mycophenolic Acid
PublicationBackground: Although Mycophenolic Acid (MPA) is applied as prodrugs in clinic as an immunosuppressant, it also possesses anticancer activity. MPA acts as Inosine-5’-Monophosphate Dehydrogenase (IMPDH) inhibitor, where the carboxylic group at the end of the side chain interacts with Ser 276 of the enzyme via hydrogen bonds. Therefore, MPA derivatives with other polar groups indicated high inhibition too. On the other hand, potent...
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Selected Methods for the Chemical Phosphorylation and Thiophosphorylation of Phenols
PublicationThis Focus Review gathers together a selection of methods for the chemical phosphorylation of phenols that employ three‐ and four‐coordinate phosphorus compounds. Phosphorylated scaffolds can exhibit enhanced properties compared to their non‐phosphorylated analogues, such as increased biological activity and increased/decreased solubility; as such, phosphorus compounds have gained more and more interest in organic and medicinal...
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Analytical chemistry with biosolvents
PublicationOne of the current trends in green analytical chemistry is the introduction of green solvents, some of which are biobased. At the same time, the development of the biorefinery concept has allowed more biochemicals to be obtained with increased efficiency and from a wider range of feedstocks. The first examples of the use of biosolvents in analytical applications included extractions performed with alcohols, esters, and terpenes....
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Dual functionality of amphiphilic 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids: surfactants with catalytic function
PublicationA series of amphiphilic 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids were synthesized. Acidic hydrogen sulfate ionic liquids with the alkyl chains C6–C14 are characterized by good surface properties. Their surface properties (adsorption and micellization parameters, degree of ionization of micelles, Krafft temperatures and thermodynamic parameters) were determined. Synthesized ionic liquids were applied as a co-catalyst...
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Kobieta ciężarna i alkohol-toksyczny związek. Smółka noworodków jako materiał w diagnostyce spożywania alkoholu w czasie ciąży
PublicationKażda ilość alkoholu spożyta przez ciężarną kobietę może spowodować poronienie, przedwczesny poród, patologię łożyska, zahamowanie wzrostu wewnątrzmacicznego płodu i wystąpienie licznych wad wrodzonych wywołanych alkoholem, określanych wspólnie mianem spektrum płodowych zaburzeń alkoholowych - FASD. Mogą one objawiać się zaburzeniami psychicznymi i/lub fizycznymi. Współczesna diagnostyka u noworodków zespołu FASD opiera się najczęściej...
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Separation and determination of the group-type composition of modern base and lubricating oils with a wide range of polarity, especially emitted to the environment
PublicationLubricating oils are composed of base oils (>85% v/v) and enriching additives (<15% v/v). Three types of base oils may be distinguished: 1) traditional bases (obtained by low-volatile fractions from crude oil distillation refining), 2) synthetic bases (mainly poly-alpha-olefins, sometimes esters, especially succinic acid esters), 3) bases of natural origin (especially obtained from refined plant oils). The bases of natural origin...
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1,3-alternate calix[4]arene-bonded silica stationary phases. Effect of calixarene skeleton substituents on the retention mechanism and column selectivity
PublicationFour novel 1,3-alternate calix[4]arene-bonded silica gel stationary phases possessing different aromatic and aliphatic substituents at the upper rim (CalixNph, CalixBph, CalixHex and CalixDdc) were prepared and structurally characterized. The comparison and selectivity of these phases was done by using alkylbenzenes, fatty acid p-bromophenacyl esters, aromatic positional isomers and polynuclear aromatic hydrocarbons as analytes....
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Cuticular lipids of insects as potential biofungicides
PublicationThe term ''lipids'' refers to fatty acids, their derivatives and substances related with them biochemically or by the functions in the body. Lipids include compounds with different chemical structure. There are lipids with structures based on long-chain carboxylic acids and their direct derivatives, namely: fatty acids, alkanes, some alkenes, aldehydes and long chain alcohols and their derivatives (esters). The variety of lipid...
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Environmental risk- based ranking of solvents by the combination of multimedia model and multi-criteria decision analysis
PublicationA novel procedure for assessing the environmental risk related to solvents emissions has been developed. The assessment of risk is based on hazard and exposure detailed investigations. The potential exposure related to different environmental phases is calculated with basic multimedia model, that gives the percentage distribution of solvent in environmental compartments as a result. Specific hazards– toxicological, environmental...
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TMSCL as a rate accelerating additive in acylations of amines with 5-(α- amino-α'-hydroxy)methylene meldrum's acids
PublicationAspects are presented of the acylation of amines, alcohols and thiols with 5-(α-amino- α'-hydroxy)methylene Meldrum's acids. We placed special emphasis on the acylation reaction of secondary amines with 5-(α-amino- α'-hydroxy)methylene Meldrum's acids, which, due to their basicity, caused problems concerning salt formation with a Meldrum acid derivative. We found that secondary amines, which react at the slowest rate and with a...
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Synthesis and polymerisation techniques of molecularly imprinted polymers
PublicationMolecularly Imprinted Polymers (MIPs) are materials that has been processed using the molecular imprinting technique which permit to obtain well-defined three-dimensional cavities, with affinity to a template molecule, in the polymer matrix. Technology involves three strategies, i.e., covalent, non-covalent and semi-covalent approach, but the most popular is non-covalent approach. The most important components for the synthesis...
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Monetary values estimates of solvents emissions
PublicationThe impact values for environmental emissions of 52 solvents are estimated and expressed in monetary units. The impact values of solvents present in the air are calculated on the basis of 13 impact indicators and for solvents present in water on additional 2 impact indicators. These impact values are weighted with the results obtained with multi-compartment distribution model, allowing to calculate the fraction of solvent emitted...
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Tmscl as a rate accelerating additive in acylations of amines with 5-(α-amino- α'-hydroxy)methylene meldrum's acids
PublicationAspects are presented of the acylation of amines, alcohols and thiols with 5-(α-amino- α'-hydroxy)methylene Meldrum's acids. We placed special emphasis on the acylation reaction of secondary amines with 5-(α-amino- α'-hydroxy)methylene Meldrum's acids, which, due to their basicity, caused problems concerning salt formation with a Meldrum acid derivative. We found that secondary amines, which react at the slowest rate and with a...
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Synthesis of amides under microwave irradiation
PublicationAmides belong to the most important carboxylic acid derivatives. They are constituents of natural compounds like peptides and proteins. They found applications in many branches of science and industry, especially in pharmaceutical and polymer science. Conventional procedures for amide preparation involve reaction between amine and carboxylic acid or their more active derivatives such as acid chlorides, acid anhydrides or esters....
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Selected Aspects of Biofuels Market and the Electromobility Development in Poland: Current Trends and Forecasting Changes
PublicationThis work presents basic information associated with markets of selected alternative fuels used in transport, such as methyl esters, conventional bioethanol and lignocellulosic bioethanol, and the market of electrical vehicles. Legal conditions, which stimulate development and regulate the mode of functioning of the liquid biofuel market until 2020 are discussed, based on provisions of EU directives. Data on biofuel production...
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Studies on origin of Polish honeys by two-dimensional gas chromatography Ocena pochodzenia surowcowego polskich miodów przy użyciu dwuwymiarowej chromatografii gazowej
PublicationPolish acacia, linden, rapessed and buckwheat-derived honeys and a honydew were analysed for presence of hydrocarbons, alcs., ketones and esters by 2-dimensional gas chromatog. to establish the markers for the honey origin. PrOH was found characteristic for acacia honey, Me(CH2)11OH for linden honey, Me(CH2)6CHOMe for honeydew and Me(CH2)8COOEt for the rapeseed honey. Wykorzystano technikę dwuwymiarowej chromatografii gazowej sprzężonej...
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Non-volatile molecular composition and discrimination of single grape white of chardonnay, riesling, sauvignon blanc and silvaner using untargeted GC–MS analysis
PublicationThis study developed and applied a GC–MS method aiming at molecular fingerprinting of 120 commercial single grape white wines (Chardonnay, Riesling, Sauvignon Blanc and Silvaner) for possible authentication according to grape variety. The method allowed detection of 372 peaks and tentative identification of 146 metabolites including alcohols, organic acids, esters, amino acids and sugars. The grape variety effect explained 8.3%...
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A review on homogeneous and heterogeneous catalytic microalgal lipid extraction and transesterification for biofuel production
PublicationExtracting lipids from microalgal biomass presents significant potential as a cost-effective approach for clean energy generation. This can be achieved through the chemical conversion of lipids to produce fatty acid methyl esters via transesterification. The extraction mainly involves free fatty acids, phospholipids, and triglycerides, and requires less energy, making it an attractive option for satisfying the growing demand for...
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Virulence, antifungal susceptibility and molecular mechanisms of echinocandin resistance among Candida isolates recovered from clinical specimens
PublicationFungi of the genus Candida belong to the natural microflora of healthy individuals. However, they can also be a cause of opportunistic infections especially among patients with an impaired immune system. The first line therapy of Candida infections is based on triazoles. However, in recent years there an increase of azole resistant Candida spp., in particular C. glabrata and C. krusei, has been observed. For this reason, echinocandin...
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The Analysis of Vodka: A Review Paper
PublicationVodka is the most popular alcoholic beverage in Poland, Russia and other Eastern European countries, made from ethyl alcohol of agricultural origin that has been produced via fermentation of potatoes, grains or other agricultural products. Despite distillation and multiple filtering, it is not possible to produce 100 % ethanol. The solution with a minimum ethanol content of 96 %, which is used to produce vodkas, also contains trace amounts...
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Acetate-Induced Disassembly of Spherical Iron Oxide Nanoparticle Clusters into Monodispersed Core−Shell Structures upon Nanoemulsion Fusion
PublicationIt has been long known that the physical encapsulation of oleic acid-capped iron oxide nanoparticles (OA−IONPs) with the etyltrimethylammonium (CTA+) surfactant induces the formation of spherical iron oxide nanoparticle clusters (IONPCs). However, the behavior and functional properties of IONPCs in chemical reactions have been largely neglected and are still not well-understood. Herein, we report an unconventional ligand-exchange...
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Photoelectrochemically Active N‐Adsorbing Ultrathin TiO2 Layers for Water‐Splitting Applications Prepared by Pyrolysis of Oleic Acid on Iron Oxide Nanoparticle Surfaces under Nitrogen Environment
PublicationHighly performing photocatalytic surfaces are nowadays highly desirable in energy fields, mainly due to their applicability as photo water‐splitting electrodes. One of the current challenges in this field is the production of highly controllable and efficient photoactive surfaces on many substrates. Atomic layer deposition has allowed the deposition of photoactive TiO2 layers over wide range of materials and surfaces. However,...
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In-tube extraction for the determination of the main volatile compounds in Physalis peruviana L
PublicationAn analytical procedure based on in-tube extraction followed by gas chromatography with mass spectrometry has been developed for the analysis of 24 main volatile components in cape gooseberry (Physalis peruviana L.) samples. According to their chemical structure, the compounds were organized into different groups: one hydrocarbon, one aldehyde, four alcohols, four esters, and 14 monoterpenes. By single-factor experiments, incubation...
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Betaine and L-carnitine ester bromides: Synthesis and comparative study of their thermal behaviour and surface activity
PublicationSix esters of both betaine and L-carnitine bromides, featuring alkyl groups ranging from C8 to C18 in length, have been synthesized. The thermal behaviour of these twelve bio-based salts has been analyzed and compared by thermal gravimetric analysis and differential scanning calorimetry. The L-carnitine alkyl ester bromides melted below 100 C and can hence be considered ionic liquids (ILs) with full rights. Conversely, the betaine...
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Phenolic compounds from Nerium oleander leaves: microwave assisted extraction, characterization, antiproliferative and cytotoxic activities
PublicationA microwave-assisted extraction (MAE) method was used for the extraction of phenolic compounds from Nerium oleander leaves. The influence of variables such as ethanol concentration, microwave power, irradiation time and liquid/solid ratio on polyphenol extraction was modelled using a second-order regression equation based on response surface methodology (RSM). The optimal conditions for MAE were: extraction solvent 35% ethanol...
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Vaccinium Species—Unexplored Sources of Active Constituents for Cosmeceuticals
PublicationThe genus Vaccinium is represented by shrubs growing in a temperate climate that have been used for ages as traditional remedies in the treatment of digestive problems, in diabetes, renal stones or as antiseptics due to the presence of polyphenols (anthocyanins, flavonoids and tannins) in their fruits and leaves. Recent studies confirm their marked potential in the treatment of skin disorders and as skin care cosmetics. The aim...
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Biomarkers of alcohol consumption in body fluids - possibilities and limitations of application in toxicological analysis
PublicationEthyl alcohol is the most popular legal drug, but its excessive consumption causes social problems. Despite many public campaigns against alcohol use, car accidents, instances of aggressive behaviour, sexual assaults and deterioration in labor productivity caused by inebriated people is still commonplace. Fast and easy diagnosis of alcohol consumption is required in order to introduce proper and effective therapy, and is crucial...
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RAPESEED PELLET - A BYPRODUCT OF BIODIESEL PRODUCTION - AS AN EXCELLENT RENEWABLE ENERGY SOURCE
PublicationVegetable oils are renewable feedstock currently being used for production of biofuels from sustainable biomass resources. The existing technology for producing diesel fuel from plant oils, such as rapeseed, soybean, canola and palm oil are largely centered on transesterification of oils with methanol to produce fatty acid methyl esters (FAME) or biodiesel. Rapeseed pellet - crushed seed residue from oil extraction is a byproduct...
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Authenticity Assessment of the "Onisiówka" Nalewka Liqueurs Using Two-Dimensional Gas Chromatography and Sensory Evaluation
PublicationThe “Onisiówka” nalewka liqueur is a regional Polish alcoholic beverage, which is inscribed on the list of regional and traditional products of the Ministry of Agriculture and Rural Development in Poland. It is produced from multiflower honey, black elderberry flower syrup, and spirit. Due to fact that the “Onisiówka” nalewka liqueur has never been investigated, these studies are the foundation for further work on this regional...
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Przegląd metod zagospodarowania odcieku glicerynowego z procesu produkcji biopaliwa rzepakowego
PublicationZagospodarowanie fazy glicerynowej - produktu odpadowego powstającego podczas wytwarzania estrów metylowych oleju rzepakowego (RME - Rapeseed Methyl Esters), jest ważnym elementem wspierającym produkcję biopaliw zarówno w aspekcie ekonomicznym, jak i ekologicznym. Rafinerie wytwarzające biodiesla na skalę przemysłową stosują najczęściej technologie oczyszczania fazy glicerynowej do postaci czystej gliceryny, możliwej do zastosowania...
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Estimating the Impact of Inflow on the Chemistry of Two Different Caldera Type Lakes Located on the Bali Island (Indonesia)
PublicationThis paper is a preliminary attempt to assess the composition of pollutants in two different caldera lakes situated in the Indonesian Archipelago: Batur and Bratan. Both lakes are characterized by largely different physico-chemical regimes; Batur Lake is located in an area that is currently volcanically active, unlike Bratan Lake. The latter is much smaller and shallower than Batur Lake. The concentration of pollutants in the Indonesian...
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Sample preparation procedure using extraction and derivatization of carboxylic acids from aqueous samples by means of deep eutectic solvents for gas chromatographic-mass spectrometric analysis
PublicationThe paper presents a new procedure for the determination of organic acids in a complex aqueous matrixusing ultrasound-assisted dispersive liquid–liquid microextraction followed by injection port derivati-zation and GC–MS analysis. A deep eutectic solvent (choline chloride: 4-methylphenol in a 1:2 mol ratio)was used both as an extracting solvent and as a derivatizing agent to yield ion pairs which were next con-verted to methyl...
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Renewable Resources for Polyurethanes and Polyurethane Composites: A Review
PublicationEach year, more than two million tons of polyurethane is produced in the EU by reacting isocyanates with polyols made from fossil fuel. In addition, there are appreciable quantities of petroleum based functional additives applied in the industry nowadays for both polyols and polyurethane materials. It is therefore of key importance to develop sustainable economically viable polyols with enhanced functionalities, and thereby reducing...
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Synthesis of phosphono and phosphate derivatives of hydroxyimino-D-alditols as new potential antifungal agents
PublicationIn search for new effective we antyfungals we focus on two enzymes involved in biosynthesis of the fungal cell wall. The first enzyme is glucosamine-6-phosphate (GlmS), which catalyzes transformation of D-fructose-6-phosphate (Fru-6P) to D-glucosamine-6-phodphate (GlcN-6P) in the chitin biosynthesis pathway. The second enzyme is phosphomannose isomerase (PMI) repored to play a crucial role in biosynthesis of many mannosylated structures,...
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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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Volatile Compound Emissions from Stereolithography Three-Dimensional Printed Cured Resin Models for Biomedical Applications
PublicationStereolithography three-dimensional printing is used increasingly in biomedical applications to create components for use in healthcare and therapy. The exposure of patients to volatile organic compounds (VOCs) emitted from cured resins represents an element of concern in such applications. Here, we investigate the biocompatibility in relation to inhalation exposure of volatile emissions of three different cured commercial resins...
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New 2-[(4-Amino-6-N-substituted-1,3,5-triazin-2-yl)methylthio]-N-(imidazolidin-2-ylidene)-4-chloro-5-methylbenzenesulfonamide Derivatives, Design, Synthesis and Anticancer Evaluation
PublicationIn the search for new compounds with antitumor activity, new potential anticancer agents were designed as molecular hybrids containing the structures of a triazine ring and a sulfonamide fragment. Applying the synthesis in solution, a base of new sulfonamide derivatives 20–162 was obtained by the reaction of the corresponding esters 11–19 with appropriate biguanide hydrochlorides. The structures of the compounds were confirmed...
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No Evidence for Sex-specificity in Vitamin C, E and Fatty Acid Content of Human Milk from Healthy Polish Mothers
PublicationHuman milk (HM) is a complex fluid that meets the nutritional needs of infants. Its composition idrfs associated with environmental, maternal, and foetal variables. It provides nutrients and bioactive substances, including cytokines, immunoglobulins, and constituents with antioxidative properties. Boys are reportedly more susceptible to oxidative stress. This study aimed to determine the relationship between infant sex and the...