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Application of safirinium N-hydroxysuccinimide esters to derivatization of peptides for high-resolution mass spectrometry, tandem mass spectrometry, and fluorescent labeling of bacterial cells
PublicationMass spectrometry methods are commonly used in the identification of peptides and biomarkers. Due to a relatively low abundance of proteins in biological samples, there is a need for the development of novel derivatization methods that would improve MS detection limits. Hence, novel fluorescent N-hydroxysuccinimide esters of dihydro-[1,2,4]triazolo[4,3-a]pyridin-2-ium carboxylates (Safirinium P dyes) have been synthesized. The...
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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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Nuclear Magnetic Resonance data for the synthesis of esterase cleavable antifungal conjugates containing fatty acids as molecular carriers
Open Research DataNMR data for novel organic compounds - conjugates composed of C2-18 fatty acid (FA) residues as a molecular carrier and 5-fluorocytosine (5-FC) as an active agent, released upon the action of intracellular esterases on the ester bond between FA and “trimethyl lock” intramolecular linker.
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The imidazoacridinone C-1311 induces p53-dependent senescence or p53-independent apoptosis and sensitizes cancer cells to radiation
PublicationC-1311 is a small molecule, which has shown promise in a number of preclinical and clinical studies. However, the biological response to C-1311 exposure is complicated and has been reported to involve a number of cell fates. Here, we investigated the molecular signaling which determines the response to C-1311 in both cancer and non-cancer cell lines. For the first time we demonstrate that the tumor suppressor, p53 plays a key role...
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Electrospinning as a useful technique for the encapsulation of living bifidobacteria in food hydrocolloids
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Electromodulation of monomer and excimer phosphorescence in vacuum-evaporated films of platinum (II) complexes of 1,3-di(2-pyridyl)benzenes
PublicationElectric field-modulated photoluminescence (EML) measurements are presented for vacuum-evaporated films of cyclometallated Pt (II) complexes of 1,3-di(2-pyridyl) benzenes used as triplet emitters in organic light-emitting diodes (OLEDs). The excimer phosphorescence is quenched by the external electric field of 2.5 MV/cm up to 25% but the same effect on monomer phosphorescence is one order of magnitude smaller. The higher quenching...
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Development and validation of a method for the simultaneous analysis of fatty acid ethyl esters, ethyl sulfate and ethyl glucuronide in neonatal meconium: application in two cases of alcohol consumption during pregnancy
PublicationAlcohol consumption during pregnancy constitutes one of the leading preventable causes of birth defects and neurodevelopmental disorders in the exposed children. Fatty acid ethyl esters (FAEEs), ethyl glucuronide (EtG) and ethyl sulfate (EtS) have been studied as potential biomarkers of alcohol consumption. However, most analytical approaches proposed for their analysis in meconium samples consist of separated extraction procedures...
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The activity of latent benzoperimidine esters to inhibit P-glycoprotein and multidrug resistance-associated protein 1 dependent efflux of pirarubicin from several lines of multidrug resistant tumor cells.
PublicationZaprezentowano wyniki badań biologicznych przeprowadzonych dla nowej grupy związków: estrów benzoperymidyny z zastosowaniem wybranych linii komórek nowotworowych: wrażliwych i opornych o oporności P-gp-zależnej, MRP1-zależnej i o oporności związanej z nadekspresją białek MRP1/LRP. Metodą spektrofluorymetryczną zbadano zdolność estrów benzoperymidyny do hamowania eksportu aktywnego pirarubicyny z komórek opornych. Estry benzoperymidyny...
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Evaluation of the geranyl esters-containing pheromone traps used for monitoring Elateridae family beetles in crops Ocena pułapek feromonowych zawierających estry geranylu stosowanych do monitorowania chrząszczy z rodziny Elateridae w uprawach
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Anticancer Imidazoacridinone C-1311 is Effective in Androgen-Dependent and Androgen-Independent Prostate Cancer Cells
PublicationAndrogen receptor (AR) plays a crutial role in prostate cancer (PCa) development and metastasis. Here, we reported potent anti-PCa activity of a small molecule imidazoacridinone C-1311. In AR-positive PCa cells, C-1311 was found to inhibit the transcriptional activity of AR uncovering a novel mechanism that may be relevant for its anticancer effect. Mechanistically, C-1311 decreased AR binding to prostate-specific antigen (PSA)...
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Monitoring of Caged Bluefin Tuna Reactions to Ship and Offshore Wind Farm Operational Noises
PublicationUnderwater noise has been identified as a relevant pollution affecting marine ecosystems in different ways. Despite the numerous studies performed over the last few decades regarding the adverse effect of underwater noise on marine life, a lack of knowledge and methodological procedures still exists, and results are often tentative or qualitative. A monitoring methodology for the behavioral response of bluefin tuna (Thunnus thynnus)...
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A global multinational survey of cefotaxime-resistant coliforms in urban wastewater treatment plants
PublicationThe World Health Organization Global Action Plan recommends integrated surveillance programs as crucial strategies for monitoring antibiotic resistance. Although several national surveillance programs are in place for clinical and veterinary settings, no such schemes exist for monitoring antibiotic-resistant bacteria in the environment. In this transnational study, we developed, validated, and tested a low-cost surveillance and...
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The reactions of dialkyl phosphites and phosphine oxides with iodosylbenzene
PublicationThe reaction of iodosylbenzene with >P(O)H type of acids (dialkyl phosphites, secondary phosphine oxides) was studied. The acids of >P(O)H type add to iodosylbenzene to yield intermediate 6 which in the aprotic solvents yields oxidation products, it means >P(O)OH acids and/or anhydride of >P(O)OP(O)< type. On the other hand if the reaction is performed in alcohol as a solvent in the presence of sodium alcoholate >P(O)OR ester is...
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Fourier transform infrared spectroscopy (FTIR) of pre- PXBS (0 h) and PXBS during the crosslinking process (24 h–288 h)
Open Research DataThe goal of this research was developing biodegradable and biocompatibile xylitol-based copolymers with improved mechanical properties, and investigating the change in their thermal and chemical properties withprogress of the cross-linking process. Using a raw material of natural origin such as xylitol, a prepolymer wasobtained by esterification and...
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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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Products of Photo- and Thermochemical Rearrangement of 19-Membered di-tert-Butyl-Azoxybenzocrown
PublicationThe preparation and characterization of products of the photochemical and thermochemical rearrangements of 19-membered azoxybenzocrowns with two, bulky, tert-butyl substituents in benzene rings in the para positions to oligooxyethylene fragments (meta positions to azoxy group, i.e., t-Bu-19-Azo-O have been presented. In photochemical rearrangement, two colored typical products were expected, i.e., 19-membered o-hydroxy-m,m′-di-tert-butyl-azobenzocrown...
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2-Methylphenyl 2-methoxyacridine-9-carboxylate
PublicationThe title compound, C22H17NO3, crystallizes in the monoclinic space group P21/c with four molecules per unit cell. The molecules are arranged in centrosymmetric pairs, joined via the C and attached H atoms in the meta position relative to the methoxy group. These pairs are bonded in the crystalline phase as a result of non-specific dispersive interactions, and through a network of C—H⋯O interactions involving the non-bonded O...
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A novel chemiluminescent immunoassay for detection of Toxoplasma gondii IgG in human sera
PublicationThis study describes Toxoplasma gondii IgG chemiluminescent immunoassay (CLIA) based on the use of a novel immunochemical reagents in the form of the conjugates of original acridinium ester (AE) labels attached to antibodies and SAG2-GRA1-ROP1L chimeric antigen and shows that this test is useful for diagnostic purposes.
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Novel Polyurethanes as Antifouling Paint Matrices
PublicationThe new poly(ester-ether urethane)s (PEEUR) were prepared in two stage synthesis from formerly obtained oligo(alkylene ester-ether)diols (OAEE) and 4,4‘-diphenylmethane diisocyanate (MDI). PEEUR samples were subjected to crosslinking with styrene in the presence of radical polymerization initiators: methyl ethyl ketone peroxide (MEKPO) or cobalt 2-ethyl cyclohexanoate (EtHCo). Crosslinked PEEUR were characterized by their physicochemical...
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Biobased Ultralow-Density Polyurethane Foams with Enhanced Recyclability
PublicationPolyurethane (PUR) foams are widely used in many engineering applications, but their efficient recycling has remained a major challenge for many years. This study presents a novel strategy of incorporating hydrolyzable ester units into the PUR structure to enhance PUR foam recyclability. The present ecodesign concept of PUR materials enables fully the replacement of petrochemical polyols with biobased alternatives and production...
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Bioactive polyurethanes applied as a surgical implants
PublicationSynthetic materials are applied in many branches of the industry, i.a. in medicine as a casing of apparatus, elements of artificial organs (hearts, blood vessels), catheters, wound healings, intra aortic balloons, mammary implants to mention but a few. Polymeric material used in such applications must be distinguished by a good biocompatybility. Since many years extensive research are employed to develop a new polymers that can...
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Diastereoselective Synthesis of Z‐Alkenyl Disulfides from α‐Thiophosphorylated Ketones and Thiosulfonates
PublicationWe developed a simple and efficient method for the synthesis of functionalized unsymmetrical Z‐alkenyl disulfides under mild conditions in moderate to good yields. The designed method is based on the reaction of α‐thiophosphorylated carbonyl compounds with thiotosylates in the presence of a base. The developed method allows the preparation of unsymmetrical Z‐alkenyl disulfides bearing additional hydroxy, carboxy, or ester functionalities
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Comprehensive two-dimensional gas chromatography and three-dimensional fluorometry for detection of volatile and bioactive substances in some berries
PublicationThe volatilefractionsofCapegooseberryandblueberryweredeterminedbyheadspacesolid-phase microextractioncoupledwithcomprehensivetwo-dimensionalgaschromatographywithtime-of-flight mass spectrometry(HS-SPME/GCGC-TOFMS).Thehighestamountofalcohol(51.8%),ester(32.8%)and carboxylicacid(6.9%)wasinblueberryincomparisonwithgooseberryandoppositelyketones(14.7%), aldehydes(9.9%)andterpenes(8%)werefoundingooseberry.Thebioactivecompoundsandantioxidant capacities...
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SYNTHESIS OF PHOSPHORUS TACRINE ANALOGUES AS A NEW POTENTIAL ANTI-ALZHEIMER’S DISEASE AGENTS
PublicationA series of novel phosphorus tacrine derivatives was obtained in three steps, including synthesis of 9-chlorotacrine, connection of 9-chlorotacrine with hexamethylenediamine, 1,8-diaminooctane and 1,12-diaminododecane linkers and reaction of obtained tacrine diamine analogues with corresponding acid ester to give nine tacrine organophosphorus compounds. All of the obtained final structures were characterized by 1H NMR, 13C NMR,...
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Do Phenyl Substituents Affect the Properties of Azobenzocrown Derivatives?
PublicationNew products of photo- and thermal rearrangements of 19-membered azoxybenzocrown with phenyl substituents in benzene rings in the para positions to oligooxyethylene fragments are characterized. The yields of photochemical transformations depend on the solvent. Para-hydroxyazocrown is formed with yields over 50% in propan-2-ol. Ortho-hydroxyazobenzocrown is obtained with yields up to 70% in toluene/acetic acid mixture. Macrocyclic...
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Waterborne polyesters partially based on renewable resources
PublicationA new experimental approach for preparing biobased, water-soluble polyesters via titanium(IV) n-butoxide-catalyzed bulk polycondensation is presented. In the described method polymers were obtained from isosorbide, maleic anhydride and poly(ethylene glycol). The chemical structure of the synthesized polyesters was confirmed using 2D NMR spectroscopy and by titration methods. Careful analysis of 2D NMR spectra viz. Correlation Spectra...
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Alternative method for the synthesis of imidazo[5,1-f][1,2,4]triazin-4(3H)-one—a substrate for the preparation of phosphodiesterase (5) inhibitors
PublicationImidazo[5,1-f][1,2,4]triazin-4(3H)-ones, as isosteres of purine, are of interest for pharmaceutical research as potential substrates for the synthesis of cGMP-PDE5 inhibitors. We present a novel, alternative method for the synthesis of imidazotriazinones, that differs from the previously reported ones with respect to the method of construction of the triazinone ring in the molecule. The key step in our approach is condensation...
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Fatty acids as molecular carriers in cleavable antifungal conjugates
PublicationConjugates composed of C2-18 fatty acid (FA) residues as a molecular carrier and 5-fluorocytosine (5-FC) as an active agent, released upon the action of intracellular esterases on the ester bond between FA and “trimethyl lock” intramolecular linker, demonstrate good in vitro activity against human pathogenic yeasts of Candida spp. The minimal inhibitory concentrations (MIC) values for the most active conjugates containing caprylic...
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Investigations on the immunosuppressive activity of derivatives of mycophenolic acid in immature dendritic cell
PublicationThe main activity of mycophenolic acid (MPA) and its analogs is the inhibition of proliferation of T cells. Here, we hypothesized that MPA and its conjugates inhibits also the activity of antigen-presenting cells (APC) including dendritic cells (DCs). We tested the effect of novel amino acid derivatives of MPA and conjugates of MPA with acridines/acridones on DCs by flow cytometry, ELISA and MLR assay. Both acridines/acridone derivatives...
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Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction
PublicationThe simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of S-vinyl phosphorodithioate with thiotosylates or S-vinyl thiotosylate with thiols. The designed methods allow for the synthesis of unsymmetrical vinyl disulfides with additional functionalities...
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Immunosuppressive properties of amino acid and peptide derivatives of mycophenolic acid
PublicationMycophenolic acid (MPA) was coupled with amino acids and biologically active peptides including derivatives of tuftsin to modify its immunosuppressive properties. Both amino acid unit in the case of simple MPA amides and modifications within peptide moiety of MPA - tuftsin conjugates influenced the observed activity. Antiproliferative potential of the obtained conjugates was investigated in vitro and MPA amides with threonine methyl...
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Emulsifi ers from renewable materials: an eco-friendly synthesis and properties
PublicationThe focus of this study was the preparation of novel bio based polyglycerol emulsifiers characterized by a one pot synthesis, thus by modified properties with respect to interfacial activity and effectiveness as emulsion stabilizers. The final products of the esterification process, carried out in the presence of carboxylates were used directly as emulsifiers (without purification or fractionation). Polyglycerol emulsifiers obtained...
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A simple access to o-acyl bicyne
PublicationW publikacji przedstawiono prostą metodę otrzymywania o-acylowych pochodnych bicyny. Substratem do syntezy była n,n-bis(2-hydroksyetylo)glicyna - bicyna. Bicynę najpierw przeprowadzano w ester benzylowy w reakcji z alkoholem benzylowym i kwasem p-toluenosulfonowym w temp. 75 st. C. Tak otrzymany związek, acylowano kwasami organicznymi w obecności DCC ( dicyklokeksylokarbodiimid)i DMAP (dimetyloaminopirydyna), otrzymując o-acylowe...
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Phosphate and Thiophosphate Biphenyl Analogs as Steroid Sulfatase Inhibitors
PublicationIn the present work, we report convenient methods for the synthesis and biological evaluation of phosphate and thiophosphate biphenyl derivatives exhibiting steroid sulfatase (STS) activity. The described synthesis is based on straightforward preparation of biphenyl-4-ol and 40-hydroxybiphenyl- 4-carboxylic acid ethyl ester modified with various phosphate or thiophosphate moieties. The inhibitory effects of these compounds were...
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Boron-doped TiO2: Characteristics and photoactivity under visible light
PublicationOtrzymano TiO2 domieszkowany borem aktywny w reakcjach fotodegradacji pod wpływem światła widzialnego (λ>400 nm). Fotokatalizatory otrzymano poprzez hydrolizę tytanianu(IV) izopropylu w obecności związków boru lub poprzez ucieranie TiO2 (ST-01, P25 i A11) z prekursorami B i następnie kalcynację w zakresie temperatur 200-600oC. Jako źródło boru zastosowano kwas borowy lub ester trietylowy kwasu borowego. Najwyższą aktywność pod...
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Water sorption and blistering of GFRP laminates with varying structures
PublicationThe microstructures, water absorption as well as blistering was studied for bi- and tri- axial glass fibre vinyl ester and polyester -matrix laminates coated with gel coat layer and uncoated. The effect of manufacturing technique on water sorption characteristics was considered. It was found that water sorption characteristics of GFRP depend on manufacturing methods. The least water intake was found for specimens having perfect...
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Preparation and photocatalytic activity of B-doped titanium dioxide
PublicationOtrzymano TiO2 domieszkowany borem, aktywny w reakcjach fotodegradacji pod wpływem światła widzialnego (λ>400 nm). Fotokatalizatory otrzymano poprzez hydrolizę tytanianu(IV) izopropylu w obecności związków boru lub poprzez ucieranie ST-01 z prekursorami B i następnie kalcynację w temperaturze 450stC. Jako źródło boru zastosowano kwas borowy (0,5 i 10%wag.) lub trietylo ester kwasu borowego (0,5; 1; 5 i 10%wag.). Najwyższą aktywność...
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Hydro Lubricants: Water-based lubricants for hydropower applications
PublicationSeveral different base oil types exist in the market including mineral and synthetic oils (e.g. polyalphaolefins, ester, polyglycol, etc.) and are currently widely in use. Although synthetic oils have drawn great attention over the past few decades in terms of their tribological benefits, mineral oils are still widely used in hydropower applications due primarily to their low cost and easy miscibility with other oils. However,...
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Antifungal Activity of Homoaconitate and Homoisocitrate Analogs
PublicationThirteen structural analogs of two initial intermediates of the L-alpha-aminoadipate pathway of L-lysine biosynthesis in fungi have been designed and synthesized, including fluoro- and epoxy-derivatives of homoaconitate and homoisocitrate. Some of the obtainedcompounds exhibited at milimolar range moderate enzyme inhibitory properties against homoaconitase and/or homoisocitrate dehydrogenase of Candida albicans. The structural...
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Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives
Publication6-Sulfo-6-deoxy-D-glucosamine (GlcN6S), 6-sulfo-6-deoxy-D-glucosaminitol (ADGS) and their N-acetyl and methyl ester derivatives have been synthesized and tested as inhibitors of enzymes catalyzing reactions of the UDP-GlcNAc pathway in bacteria and yeasts. GlcN6S and ADGS at micromolar concentrations inhibited glucosamine-6-phosphate (GlcN6P) synthase of microbial origin. The former was also inhibitory towards fungal GlcN6P N-acetyl...
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Anti-cancer effect of Rumex obtusifolius in combination with arginase/nitric oxide synthase inhibitors via downregulation of oxidative stress, inflammation, and polyamine synthesis
PublicationCancer continues to be a leading cause of death worldwide, making the development of new treatment methods crucial in the fight against it. With cancer incidence rates increasing worldwide, ongoing research must focus on identifying new and effective ways to prevent and treat the disease. The combination of herbal extracts with chemotherapeutic agents has gained much interest as a novel strategy to combat cancer. Rumex obtusifolius...
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Chemiluminogenic acridinium salts: A comparison study. Detection of intermediate entities appearing upon light generation
PublicationThe nine derivatives of acridine-9-carboxylic acid (CMADs) capable for chemiluminescence (CL), representing various classes of compounds were isolated in a chemically pure state (assessed by RP-HPLC) and identified using high resolution mass spectrometry (ESI-QTOF) and magnetic resonance (1H NMR) techniques. Among them are aryl acridinium esters, containing certainly selected and located substituents in both aromatic systems, an...
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Photocatalytic activity of boron-modified TiO2 under visible light: The effect of boron content, calcination temperature and TiO2 matrix
PublicationPrzedstawiono wpływ temperatury kalcynacji (200, 300, 350, 400, 450 oraz 600oC) na fotoaktywność w świetle widzialnym (l> 400 nm) oraz właściwości powierzchniowe TiO2 modyfikowanego borem. B-TiO2 został przygotowany metodą impregnacji powierzchniowej. Jako prekursor bory wykorzystano ester trietylowy kwasu borowego (BATE). Charakterystyka otrzymywanych fotokatalizatorów obejmowała wyznaczenie powierzchni właściwej, właściwości...
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Application of microturbines in CHP systems with reciprocating engines
PublicationThe analysis was carried out for Combined Heat and Power generation systems with micro-turbines power plants working on heat rejected from the reciprocating engine. The calculations were performed for GE Jerbacher engines of J320 GS- C05, J320 GS- C25 and J416 GS- B05 types. We considered different working media (both wet and dry fluids): water, ammonia, ethanol, methanol, methylacetylene (propyne), dimethyloether, sulphur dioxide,...
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Electronic state spectroscopy by high-resolution vacuum ultraviolet photoabsorption, He(I) photoelectron spectroscopy and ab initio calculations of ethyl acetate
PublicationThe high-resolution vacuum ultraviolet photoabsorption spectrum of ethyl acetate, C4H8O2, is presented over the energy range 4.5−10.7 eV (275.5−116.0 nm). Valence and Rydberg transitions and their associated vibronic series observed in the photoabsorption spectrum, have been assigned in accordance with new ab initio calculations of the vertical excitation energies and oscillator strengths. Also, the photoabsorption cross sections...
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The structure of novel polyurethanes containing synthetic poly[(R,S)-3-hydroxybutyrate]
PublicationThe aim of this study was to estimate the structure of new polyurethanes with the potential to be used in medicine. Atactic poly[(R,S)-3-hydroxybutyrate], obtained via a ring-opening polymerization, and polycaprolactonediol or polyoxytetramethylenediol were used to built the soft segments. 4,4'-methylene dicyclohexyl diisocyanate and 1,4-butanediol were the components to form hard segments. Polyurethanes with low-molecular weight...
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Isobutyl acetate: electronic state spectroscopy by high-resolution vacuum ultraviolet photoabsorption, He(I) photoelectron spectroscopy and ab initio calculations
PublicationThe high-resolution vacuum ultraviolet photoabsorption spectrum of isobutyl acetate, C6H12O2, is presented here and was measured over the energy range 4.3–10.8 eV (290–115 nm). Valence and Rydberg transitions with their associated vibronic series have been observed in the photoabsorption spectrum and are assigned in accordance with new ab initio calculations of the vertical excitation energies and oscillator strengths. The measured...
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Collagen and hyaluronic acid hydrogel in water-in-oil microemulsion delivery systems
PublicationThe efficacy of microemul-sion in dermal and transdermal delivery of active ingredients. Here, we assessed the water-in-oilmicroemulsion capacity to incorporate two natural polymers, i.e. collagen and hyaluronic acid withlow and high molecular weight. Systems were extensively characterized in terms of conductivity, phaseinversion studies, droplet diameter, polydispersity index and rheological properties. The results of thisresearch...
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Topochemical, Single‐Crystal‐to‐Single‐Crystal [2+2] Photocycloadditions Driven by Chalcogen‐Bonding Interactions
PublicationThe face-to-face association of (E)-1,2-di(4-pyridyl)ethylene (bpen) molecules into rectangular motifs stabilized for the first time by chalcogen bonding (ChB) interactions is shown to provide photoreactive systems leading to cyclobutane formation through single-crystal-to-single-crystal [2+2] photodimerizations. The chelating chalcogen bond donors are based on original aromatic, ortho-substituted bis(selenocyanato)benzene derivatives...
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Preparation and photocatalytic activity of boron-modified TiO2 under UV and visible light
PublicationOtrzymano TiO2 domieszkowany borem i wyznaczono jego aktywność fotokatalityczną w zakresie światła UV i Vis. Katalizatory otrzymano metodą zol-żel lub poprzez ucieranie dwutlenku tytanu z prekursorami B. Jako źródło boru zastosowano kwas borowy lub ester trietylowy kwasu borowego. Fotoaktywność próbek badano w reakcji degradacji fenolu (Co = 0,21 mmol/dm3 ) w zakresie światła Vis lub UV. Obecność węgla i boru we wszystkich przygotowanych...