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Improvement of opipramol base solubility by complexation with β-cyclodextrin
PublicationOpipramol (OPI), a tricyclic antidepressant and anxiolytic compound, is administered orally in the form of a dihydrochloride. Salt form of the drug has a higher solubility in water and hence bioavailability and stability. A similar effect can be achieved by closing the hydrophobic part of the drug molecule in the cyclodextrin cavity. The paper presents opipramol inclusion complexes with beta-cyclodextrin (β-CD) in 1:1 molar ratio....
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1,3,4-Thiadiazole-based diamides: Synthesis and complexation properties
PublicationAromatic diamides, derivative of 2,6-pyridinedicarboxylic acid and isophthalic acid, bearing 1,3,4-thiadiazole residue were prepared with satisfactory yields in conventional procedures and microwave stimulated reactions. X-ray structure of N,N-bis (1,3,4-thiadiazol-2-yl)-2,6-pyridinedicarboxamide (2) DMSO solvate (2DMSO) was described. Selective zinc(II), lanthanum(III), terbium(III) and L-tyrosine recognition was found for N,N-bis(1,3,4-thiadiazol-2-yl)-2,6-pyridinedicarboxamide...
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Zinc(II) complexation by some biologically relevant pH buffers
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The template synthesis and complexation properties of the methoxypyrogal-lo[4]arene
PublicationZaprezentowano metodę syntezy templatowej MPA. Obserwowano kompleksowanie silnych akceptorów elektronów przez MPA. Analiza widm ESI-MS wykazała właściwości kompleksujące w stosunku do kationów metali alkalicznych. Właściwości jonoforowe związku badano w membranowych elektrodach jonoselektywnych.
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Effect of Hydroxypropylation and Beta-Amylase Treatment on Complexation of Debranched Starch With Naringenin
PublicationNaringenin exhibits many health benefits but it has limited water solubility and consequently low bioavailability. The objective of this study is to investigate the effect of hydroxypropylation and enzymatic treatments on starch complexation with naringenin. Potato starch and Hylon VII are hydroxypropylated to two substitution degrees and then debranched or debranched/β‐amylase treated prior to complexing with naringenin. Both...
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Effect of Acetylation and Beta‐Amylase Treatment on Complexation of Debranched Starch with Naringenin
PublicationStarch inclusion complexation has been shown to improve solubility of water insoluble molecules. Potato starch and Hylon VII are acetylated at two levels and then debranched alone or combined with β‐amylase hydrolysis, and its complexes with naringenin are prepared in aqueous conditions and characterized in this study. Both soluble and insoluble complexes are formed with the soluble complex present in the supernatant and the insoluble...
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Azomacrocyclic derivatives of imidazole: synthesis, structure, and metal ion complexation properties
PublicationNew azocrown ethers comprising imidazoles in the macrocycle have been synthesized. Imidazole, 2-methyl-, 4-methyl-, and 4-phenylimidazole were incorporated to form macrocyclic units by coupling with the appropriate bis-diazonium salts. The syntheseswere performed under high dilution conditions. The X-ray structure of a water adduct of the 21-membered crown ether derivative of 4-methylimidazole 8 has been solved. Metal...
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Helicity Discrimination in Diaryl Dichalcogenides Generateded by Inclusion Complexation with Chiral Hosts
PublicationNiektóre z molekuł pozbawione centrum stereogenicznego mogą przyjmować chiralną konformację na skutek wewnętrznej rotacji wzdłuż odpowiedniego wiązania. Do grupy tej należą badane przez nas diarylodichalogenki; diarylodisiarczki, diarylodiselenki i diaryloditellurki. Niska bariera rotacji wokół wiązania chalogen-chalogen skutkuje szybką racemizacją molekuł tych związków w roztworze i uniemożliwia badanie czynności optycznej. Wykazaliśmy,...
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Kinetic studies of complexation reaction of polyoxaalkyl phosphates with Fe(III) in ethanol
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Studies of complexation of metal cations by tris(3,6-dioxaheptyl)amine in solution
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Azomacrocyclic derivatives of imidazole: synthesis, structure, and metal ion complexation properties
PublicationOtrzymano nowe azokorony zawierające resztę imidazolu w makropierścieniu. Na drodze sprzęgania z solami diazoniowymiotrzymano pochodne imidazolu 2-metylo, 4-metylo oraz 4-fenyloimidazolu. Synteza była prowadzona w warunkach wysokiego ciśnienia. Dla 21-członowej pochodnej 4-metyloimidazolu określono strukturę jej adduktu z wodą przy pomocy metod rentgenograficznych.Zdolność kompleksowania jonów metali badano spektrofotometrycznie...
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Complexation of amino acids derivatives in water by calix[4]arene phosphonic acids
PublicationSeries of the calix[4]arene phosphonic acids with various substituents at the lower rim was synthesized. Complexing properties of these receptors towards methyl esters of six amino acids strongly depended on the calix[4]arene conformation flexibility. The complex formation processes were monitored using 1H NMR spectroscopy (deuterated phosphate buffer at pD 7.3, 22 oC) and association constant values were evaluated. Inherently...
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Effect of chemical structure on complexation efficiency of aromatic drugs with cyclodextrins: The example of dibenzazepine derivatives
PublicationIt is widely believed that the hydrophobic effect governs the binding of guest molecules to cyclodextrins (CDs). However, it is also known that high hydrophobicity of guest molecules does not always translate to the formation of stable inclusion complexes with CDs. Indeed, a plethora of other factors can play a role in the efficiency of guest–CD interactions, rendering structure-based prediction of the complexation efficiency with...
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Complexation studies of 3-substituted β-diketones with selected d- and f-metal ions
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Optical activity of the guest azobenzene molecule generated by inclusion complexation with steroidal bile acids.
PublicationZsyntetyzowano krystaliczne kompleksy inkluzyjne azobenzenu z kwasami cholowym i deoksycholowym. Otrzymane związki inkluzyjne poddano badaniom przy wykorzystaniu spektroskopii dichroizmu kołowego w fazie stałej (KBr). Dodatni efekt Cottona, odpowiadający niskoenergetycznemu przejściu elektronowemu n-pi*, skorelowano z helikalnością M,M skręconej cząsteczki azobenzenu. Ponadto w celach porównawczych zmierzono dichroizm kołowy w...
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Optical activity of benzophenone and thiobenzophenone generated by spontaneous crystallization and inclusion complexation with cholic acid.
PublicationOtrzymano związki inkluzyjne benzofenonu i jego tioanalogu z kwasem cholowym. W zależności od stosowanej metody syntezy kompleksów inkluzyjnych benzofenonu powstawały one w dwóch różnych postaciach polimorficznych. Jedna z nich wykazuje istnienie cząsteczek gościa w czterech konformacjach, przy czym dominuje konformer o helikalności M. Struktura krystalograficzna kompleksu tiobenzofenonu z kwasem cholowym ujawniła obecność tylko...
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Pyrrole azocrown ethers. Synthesis, complexation, selective lead transport and ion-selective membrane electrode studies
PublicationOtrzymano nowe, 21-członowe, lipofilowe etery koronowe z jednostką pirolową i dwoma grupami azowymi jako składowymi makrocyklu. Właściwości kompleksujące tych nowych oraz dwóch wcześniej otrzymanych makrocykli zbadano w acetonitrylu. Ligandy te zostały użyte jako jonofory w badaniach konkurencyjnego transportu równomolowej mieszaniny jonów metali: Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Ag2+, Pb2+ w układzie woda(pH 4.9)/chloroform/woda(pH...
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Determination of pyridine and adenine nucleotide metabolites in Bacillus subtilis cell extract by sweeping borate complexation capillary electrophoresis
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The synthesis, x-ray structure and metal cation complexation properties of colored crown with two heterocyclic residues as a part of macrocycle
PublicationZsyntezowano nowy eter koronowy zawierający ugrupowanie azowe, resztę pirolu i pirydyny w pierścieniu makrocyklicznym. Badano zdolność kompleksowania kationów metali w acetonitrylu oraz mieszaninę acetonitryl-woda. Do pomiarów wykorzystano spektrofotometrię UV-Vis. Ustalono strukturę krystalograficzną otrzymanego związku.
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Helicity discrimination in N,N'-dibenzoyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthrolines and their thiono- and selenocarbonyl analogues by inclusion complexation with chiral diols
PublicationX-ray crystallographic analysis of the title compounds revealed that they assume a folded helical con- formation of an approximate C2 symmetry in the solid state. Dithioamide, diselenoamide and monoselenoamide were resolved to enantiomers by inclusion crystallization with optically active diols (TADDOLs). The absolute configuration of the guest molecules in the complexes was assigned as P. The optical activity of the resolved compounds...
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Molecular geometry and optical activity of N-nitroso-2,2,6,6-tetramethylpiperidines generated by spontaneous crystallization and inclusion complexation with optically active diols
PublicationTrzy N-nitrozo-2,2,6,6-tetrametylopiperydyny, których chiralność wynika z utrudnionej rotacji wokół wiązania N-N posiadającego częściowy charakter wiązania podwójnego poddano badaniom stereochemicznym i spektroskopowym. Badane związki tworzą kompleksy inkluzyjne z optycznie czynnymi gospodarzami - Taddolami, w których N-nitrozo-2,2,6,6-tetrametylopiperydyny przyjmują chiralną konformację co dowodzą ich widma CD wykonane w ciele...
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Thioamides and selenoamides with chirality solely due to hindered rotation about the C-N bond: enantioselective complexation with optically active hosts
PublicationBariera rotacji wokół wiązania C-N w tioamidach jest średnio o 3-5 kcal/mol wyższa niż w odpowiednich amidach, a w analogicznych selenoamidach wzrasta jeszcze o 1 kcal/mol. Dzięki temu związki te występują w dwu enancjomerycznych formach, których wzajemna przemiana zachodzi w wyniku rotacji wokół wiązań C-N. Bariera rotacji jest wystarczająco wysoka, aby można było podjąć próbę ich rozdziału na enancjomery w temperaturze pokojowej....
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Co-microprecipitation/flotation of trace amounts of cadmium from environmental samples through its complexation with iodide and neutralization with cetyltrimethylammonium bromide in the presence of perchlorate ions
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Lower Rim Substituted p-tert-Butyl Calix[4]arenes(V). Synthesis of New 5,11,17,22-tetrakis-p-tert-Butyl-25-27-bis(dialkoxyphosphorylmethoxy)calix[4] arenes and Cation Complexation Studies in Ion Selective Membrane Electrodes.
PublicationZaprezentowano syntezę i właściwości trzech nowych związków (2-4), bis podstawionych na dolnym obrzeżu grupami z resztą fosforylową. Związki te były badane jako jonofory w membranowych elektrodach jonoselektywnych (ISE) wykazując selektywność na kationy Rb+,K+ oraz duży i płaski kation guanidyniowyG+). Badano korelację pomiędzy stereo-strukturą związków a ich selektywnością w ISE. Stałe trwałości kompleksów z kationami metali...
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Induction of chirality in 4,4'-azopyridine by halogen-bonding interaction with optically active ditopic donors
PublicationOptically active ditopic halogen bond donors bearing two 4-iodotetrafluorophenyl groups were obtained by reaction of chiral diols with iodopentafluorobenzene. Co-crystallization of these donors with anti-4,4′-azopyridine afforded binary complexes containing infinite chains of the alternating component molecules connected by halogen bonds. The solid state CD measurements confirmed that complexation induces optical activity of the...
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Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters
PublicationThe biological activity of Cd compounds has been investigated scarce since Cd has been recognized as a human carcinogen. However, the toxicity of cadmium is comparable to the toxicity of noble metals such as Pt and Pd. The paradigm of metal toxicity has been challenged suggesting that metal toxicity is not a constant property, yet it depends on many factors like the presence of appropriate ligands. Studies on anticancer activity...
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Chromogenic derivatives of new bis(phenylhydrazono-1H-tetrazol-5-yl-acetonitriles) - synthesis and properties
PublicationDerivatives of bis(phenylhydrazono-1H-tetrazol-5-yl-acetonitriles) with oxygen and sulphur atoms in the structure of aliphatic chains were successfully synthesised. The correlation between the ligand structure and its complexation properties was investigated by absorption spectroscopy. The formation of complexes of presented compounds with metal cations (Cu2+, Ni2+, Zn2+, Co2+, Fe2+ and Pb2+) was studied. Ligands 5-8 were additionally...
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Azo group(s) in selected macrocyclic compounds
PublicationAzobenzene derivatives due to their photo- and electroactive properties are an important group of compounds finding applications in diverse fields. Due to the possibility of controlling the trans–cis isomerization, azo-bearing structures are ideal building blocks for development of e.g. nanomaterials, smart polymers, molecular containers, photoswitches, and sensors. Important role play also macrocyclic compounds well known for...
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Cation sensing by diphenyl-azobenzocrowns
PublicationMetal cations complexation and proton binding by 13- and 16-membered diphenyl-azobenzocrowns and diphenyl-hydroxyazobenzocrowns were studied in acetonitrile using spectroscopic methods: UV–vis spectroscopy, spectrofluorimetry, and 1H NMR spectroscopy. Phenyl moieties in benzene rings were found to affect binding strength alkali and alkaline earth metal cations and hydrogen ion, and affect tautomeric equilibrium of hydroxyazobenzocrowns....
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Novel Diazocrowns with Pyrrole Residue as Lead(II) Colorimetric Probes
PublicationNovel 18- and 23-membered diazomacrocycles were obtained with satisfactory yields by diazocoupling of aromatic diamines with pyrrole in reactions carried under high dilution conditions. X-ray structure of macrocycle bearing five carbon atoms linkage was determined and described. Compounds were characterized as chromogenic heavy metal ions receptors. Selective color and spectral response for lead(II) was found in acetonitrile and...
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Development of a vortex-assisted switchable-hydrophilicity solvent-based liquid phase microextraction for fast and reliable extraction of Zn (II), Fe (II), Pb (II), and Cd (II) from various baby food products
PublicationThis manuscript describes the development of a novel liquid phase microextraction (LPME) method for the extraction and determination of Zn (II), Fe (II), Pb (II), and Cd (II) in various infant/baby food and supplements products. The method is based on vortex-assisted extraction combined with a switchable-hydrophilicity solvent (SHS) sample preparation. The SHS, which undergoes reversible phase changes triggered by pH change, enables...
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Chromogenic azomacrocycles with imidazole residue: Structure vs. properties
PublicationNew diazo macrocycles linked by hydrocarbon chain bearing imidazole or 4-methylimidazole residue have been synthetized with satisfactory yield (24–55%). The structure of macrocycles was confirmed by X-ray analysis and spectroscopic methods (1H NMR, MS, FTIR). Metal cation complexation studies were carried out in acetonitrile and acetonitrile-water system. It was found that azomacrocyles form triple-decker complexes with lead(II)....
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Chromogenic amides of pyridine-2,6-dicarboxylic acid as anion receptors
PublicationThe synthesis of simple, chromogenic pyridine-2,6-dicarboxylic acid amides, derivates of isomeric nitroanilines and aminonitrophenols, and their ion binding properties are described. The ligands' response to ionic species was examined by naked eye and was studied with the use of UV-Vis spectroscopy in DMSO and its mixture with water. The effect of the localisation and the type of the substituents in aromatic rings were discussed....
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Propensity of salicylamide and ethenzamide cocrystallization with aromatic carboxylic acids
PublicationThe cocrystallization of salicylamide (2-hydroxybenzamide, SMD) and ethenzamide (2-ethoxybenzamide, EMD) with aromatic carboxylic acids was examined both experimentally and theoretically. The supramolecular synthesis taking advantage of the droplet evaporative crystallization (DEC) technique was combined with powder diffraction and vibrational spectroscopy as the analytical tools. This led to identification of eleven new cocrystals...
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Specific Binding of Cholesterol to the Amyloid Precursor Protein: Structure of the Complex and Driving Forces Characterized in Molecular Detail
PublicationC99 is the C-terminal membrane-bound fragment of the amyloid precursor protein that is cleaved by γ-secretase to release Aβ peptides, the hallmark of Alzheimer’s disease (AD). Specific interactions of C99 with cholesterol have been proposed to underlie the recognized role of cholesterol in promoting amyloidogenesis. By using molecular dynamics simulations, we studied cholesterol binding to C99 in a lipid bilayer. We determined...
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Supramolecular Synthesis Based on a Combination of Se···N Secondary Bonding Interactions with Hydrogen and Halogen Bonds
PublicationExamination of the solid state structures of 2,1,3-benzoselenadiazole complexes with hydrogen or halogen bond donors has demonstrated that the 2,1,3-benzoselenadiazole molecules preferably form centrosymmetric dimers with use of [Se–N]2 supramolecular synthon, whereas the two remaining nitrogen atoms not involved in the [Se–N]2 supramolecular interactions can act as acceptors of hydrogen or halogen bonds. Cocrystallization of selenadiazoles...
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Mobility and bioavailability of mercury in sediments of the southern Baltic sea in relation to the chemical fractions of iron: Spatial and temporal patterns
PublicationMarine sediments play a significant role as reservoirs for mercury (Hg), a bioaccumulative toxic pollutant that poses risks to human and ecosystem health. Iron (Fe) has been recognized as an influential factor in the complexation and bioavailability of Hg in sediments. However, limited studies have investigated the interactions between the chemical fractions of these elements in natural settings. This study aims to examine the...
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Molecular dynamics simulations of the affinity of chitin and chitosan for collagen: the effect of pH and the presence of sodium and calcium cations
PublicationChitosan and chitin are promising biopolymers used in many areas including biomedical applications, such as tissue engineering and viscosupplementation. Chitosan shares similar properties with hyaluronan, a natural component of synovial fluid, making it a good candidate for joint disease treatment. The structural and energetic consequences of intermolecular interactions are crucial for understanding the biolubrication phenomenon...
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Photochemical Rearrangement of a 19-Membered Azoxybenzocrown: Products and their Properties
PublicationThe preparation and characterization of products of the chemical and photochemical rearrangements of a 19-membered o,o'-azoxybenzocrown were presented. In photochemical rearrangement, besides expected product i.e. 19-membered o-hydroxy-o,o'-azobenzocrown (19-o-OH), obtained under defined conditions with 75% yield, also other macrocyclic products were isolated and identified, namely: 19-membered p-hydroxy-o,o'-azobenzocrown (19-p-OH),...
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Investigation of vortex assisted magnetic deep eutectic solvent based dispersive liquid–liquid microextraction for separation and determination of vanadium from water and food matrices: Multivariate analysis
PublicationA new and simple vortex assisted magnetic deep eutectic solvent dispersive liquid–liquid microextraction procedure (VA-MDES-DLLME) was developed for the determination of vanadium (V) in food and water samples by flame atomic absorption spectrometry (FAAS). In the extraction medium, a bis(acetylpivalylmethane) ethylenediimine (H2APM2en) was used for the complexation of V(V) in sample solution at pH 6. The VA-MDES-DLLME was optimized...
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Hierarchical MnO2 nanoflowers blooming on 3D nickel foam: A novel micro-macro catalyst for peroxymonosulfate activation
PublicationIn this work, birnessite-type δ-MnO2 nanoflowers were uniformly deposited on 3D nickel foam (NF) by one-step hydrothermal route for high-efficient activation of peroxymonosulfate (PMS) towards degradation of acid orange 7 (AO7). High specific surface area, large pore volume and 3D hierarchical structure promotes the mass and electron transfer for great catalytic activity. Low reaction energy barrier (Ea=27.5 kJ/mol) and outstanding...
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Photophysics of Untethered ZnTPP-Fullerene Complexes in Solution
PublicationThe spectroscopy and dynamic behavior of the self-assembled, Soret-excited zinc tetraphenylporphyrin (ZnTPP) plus fullerene (C60) model system in solution has been examined using steady state fluorescence quenching, nanosecond time-correlated single photon counting, picosecond fluorescence upconversion, and picosecond transient absorption methods. Evidence of ground state complexation is presented. Steady-state quenching of the...
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Metals and metal-binding ligands in wine: Analytical challenges in identification.
PublicationBackground Due to important role of metals in the vinification process as well as their impact on the human health, their content in this alcoholic beverage has been extensively studied by many researchers. It is already known that speciation of metals determines their toxicity and bioavailability as well as influences their activity. Understanding the chemistry and knowing the structures of metal complexes could have relevant...
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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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Tuning of photocatalytic activity by creating a tridentate coordination sphere for palladium
PublicationThe synthesis and characterisation of an asymmetric potential bridging ligand bmptpphz (bmptpphz = 2,17-bis(4-methoxyphenyl)tetrapyrido[3,2-a:2’,3’-c:3’’,2’’-h:2’’’,3’’’-j] phenazine) is presented. This ligand contains a 1,10-phenanthroline (phen) and a 2,9-disubstituted phen sphere and possesses a strong absorbance in the visible. Facile coordination of the phen sphere to a Ru(tbbpy)2 core leads to Ru(bmptpphz) ([(tbbpy)2Ru(bmptpphz)](PF6)2;...
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Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones
PublicationThiazolyl-hydrazones (THs) exhibit a wide spectrum of biological activity that can be enhanced by complexation with various metal ions. Zn(II) complexes with α-pyridine-1,3-TH ligands may represent an alternative to the standard platinum-based chemotherapeutics. In addition, they show photoluminescence properties and thus can be regarded as multifunctional materials. In this study, we synthesized and characterized three neutral...
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The Interaction of Heptakis (2,6-di-O-Methyl)-β-Cyclodextrin with Mianserin Hydrochloride and Its Influence on the Drug Toxicity
PublicationOne tetracyclic antidepressant, mianserin hydrochloride (MIA), has quite significant side effects on a patients’ health. Cyclodextrins, which are most commonly used to reduce the undesirable features of contained drugs within their hydrophobic interior, also have the potential to alter the toxic behavior of the drug. The present paper contains investigations and the characteristics of interaction mechanisms for MIA and the heptakis...
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Evaluation of the photoprotective effect of ˇ-cyclodextrin on the emission of volatile degradation products of ranitidine
PublicationThe process of the photo-excitation of ranitidine hydrochloride (RAN) in a solid state makes visible changes to its colour and generates an unpleasant odour. The purpose of the present study was to observe the protective effects of ˇ-cyclodextrin (CD) complexation as well as the effect of the mixture of two stoichiometries 1:1 and 1:2 (RAN:CD, IC) on the photostability of samples in a solid state. Sam- ples of inclusion complexes...
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Evaluation of the photoprotective effect of β-cyclodextrin on the emission of volatile degradation products of ranitidine
PublicationThe process of the photo-excitation of ranitidine hydrochloride (RAN) in a solid state makes visible changes to its colour and generates an unpleasant odour. The purpose of the present study was to observe the protective effects of ˇ-cyclodextrin (CD) complexation as well as the effect of the mixture of two stoichiometries 1:1 and 1:2 (RAN:CD, IC) on the photostability of samples in a solid state. Samples of inclusion complexes...
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Janusz Rachoń prof. dr hab. inż.
PeopleSprawował urząd rektora w latach 2002-2008 Urodził się 11 sierpnia 1946 r. w Nowym Sączu. Studia wyższe ukończył w 1969 r. na Wydziale Chemicznym Politechniki Gdańskiej, uzyskując tytuł magistra inżyniera chemika. W 1969 r. rozpoczął pracę na Wydziale Chemicznym Politechniki Gdańskiej, na którym uzyskał w 1975 r. doktorat, a w 1985 r. habilitację. Na stanowisko docenta został powołany w 1989 r., na stanowisko profesora nadzwyczajnego...