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Rok 2024
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Synteza małocząsteczkowych pochodnych 2-pirydonu wykazujących właściwości przeciwnowotworowe oraz przeciwbakteryjne
PublikacjaTematyka i cel badawczy niniejszej rozprawy doktorskiej dotyczy syntezy chemicznej związków heterocyklicznych z grupy 2-pirydonu wykazujących potencjał przeciwbakteryjny oraz przeciwnowotworowy. W części teoretycznej podjęto tematykę znanych fluorochinolonów oraz chinolonów wykazujących aktywność przeciwnowotworową. Dodatkowo przedstawiono nowe metody syntezy chinolonów niewymagające stosowania katalizatorów metali przejściowych...
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Multi-Analytical Techniques for the Study of Burial Clothes of Polish King Sigismund III Vasa (1566–1633) and His Wife Constance Habsburg (1588–1631)
PublikacjaThe subjects of this research are the burial clothes of Polish King Sigismund III Vasa and his wife Constance, which were woven and embroidered with silk and metal threads. Fragments of the textiles underwent spectroscopic, spectrometric, and thermogravimetric analyses. The hydrofluoric acid extraction method was improved to isolate various classes of dyes from the textile samples that had direct contact with human remains. High-performance...
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Meldrum’s acid assisted formation of tetrahydroquinolin‑2‑one derivatives a short synthetic pathway to the biologically useful scaffold
PublikacjaA new method for the preparation of tetrahydroquinolin-2-one derivatives is presented. This approach involves a two-step reaction between enaminones and acylating agents, immediately followed by electrophilic cyclization, all within a single synthesis procedure, eliminating the need to isolate intermediates. The entire process is facilitated by the use of acyl Meldrum’s acids which not only shortens the preparation time of the...
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Human carnosinases: A brief history, medicinal relevance, and in silico analyses
PublikacjaCarnosine, an endogenous dipeptide, has been found to have a plethora of medicinal properties, such as antioxidant, antiageing, and chelating effects, but with one downside: a short half-life. Carnosinases and two hydrolytic enzymes, which remain enigmatic, are responsible for these features. Hence, here we emphasize why research is valuable for better understanding crucial concepts like ageing, neurodegradation, and cancerogenesis,...
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Development of potent and effective SARS-CoV-2 main protease inhibitors based on maleimide analogs for the potential treatment of COVID-19
PublikacjaIn the present work, we report a new series of potent SARS-CoV-2 Main Protease (Mpro) inhibitors based on maleimide derivatives. The inhibitory activities were tested in an enzymatic assay using recombinant Mpro (3CL Protease from coronavirus SARS-CoV-2). Within the set of new Mpro inhibitors, 6e demonstrated the highest activity in the enzymatic assay with an IC50 value of 8.52 ± 0.44 mM. The IC50 value for Nirmatrelvir (PF-07321332,...
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Convenient and efficient N-methylation of secondary amines under solvent-free ball milling conditions
PublikacjaIn the present work, we report the development of a rapid, efcient, and solvent-free procedure for the N-methylation of secondary amines under mechanochemical conditions. After optimization of the milling parameters, a vibrational ball mill was used to synthesize 26 tertiary N-methylated amine derivatives in a short time of 20 min (30 Hz frequency) and high yields ranging from 78 to 95%. An exception was compounds having a hydroxyl...
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Bioactive and biodegradable cotton fabrics produced via synergic effect of plant extracts and essential oils in chitosan coating system
PublikacjaFunctional antibacterial textile materials are in great demand in the medical sector. In this paper, we propose a facile, eco-friendly approach to the design of antibacterial biodegradable cotton fabrics. Cotton fiber fabrics were enhanced with a chitosan coating loaded with plant extracts and essential oils. We employed Fourier-transform infrared (FTIR) and X-ray photoelectron spectroscopy (XPS), UV–Vis spectrophotometry, optical...
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A palatal prosthesis from archaeological research in the St Francis of Assisi church in Cracow (Poland)
PublikacjaThe hard palate is a septum that not only prevents food from entering between the oral and nasal cavity, but also plays an important role during breathing or speech. The presence of cavities within it negatively affects the comfort of life of people with this type of impairment. Hence, in the literature one can find examples of the use of hard palate prostheses to restore the separation between the nasal and oral cavity. During...
Rok 2023
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Substancje groźne, niebezpieczne i pożyteczne. Tom 2. Związki organiczne
PublikacjaStreszczenie W drugim tomie prezentowanej książki przedstawione zostały informacje nt. związków organicznych, ich występowania, otrzymywania, właściwości oraz zagrożeń jakie one stwarzają, a także korzyści, jakich dostarczają. Do związków organicznych zaliczane są te substancje, które zawierają atom lub atomy węgla, z pewnymi wyjątkami (szczegóły w książce). Szacunkowo, liczba znanych związków organicznych sięga kilkudziesięciu...
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Self-assembly of secondary aryl amides in cocrystals with perfluoroaryl coformers: structural analysis and synthon preferences
PublikacjaCooperation of aryl⋯perfluoroaryl stacking interactions and hydrogen bonds was utilized in the construction of six novel cocrystals of aromatic cis-amides with pentafluorobenzoic acid (pfba) and pentafluorophenol (pfp). They were obtained by crystallization from solution and structurally characterized. In four instances, the components form heterotetrameric motifs, in which amide:amide homodimer interacts symmetrically on two sides...
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Intramolecular Proton Transfer in the Radical Anion of Cytidine Monophosphate Sheds Light on the Sensitivities of Dry vs Wet DNA to Electron Attachment-Induced Damage
PublikacjaSingle-strand breaks (SSBs) induced via electron attachment were previously observed in dry DNA under ultrahigh vacuum (UHV), while hydrated electrons were found not able to induce this DNA damage in an aqueous solution. To explain these findings, crossed electron-molecular beam (CEMB) and anion photoelectron spectroscopy (aPES) experiments coupled to density functional theory (DFT) modeling were used to demonstrate the fundamental...
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Intermolecular Hydrogen Bonding Directed by Aryl–Perfluoroaryl π–π Stacking Interactions
PublikacjaThe crystal structures of five compounds capable of forming self-complementary hydrogen bonds but crystallizing as catemers or creating more complex crystal structures were compared with their complexes prepared by cocrystallization with perfluoroaryl compounds. The results of X-ray diffraction revealed that in all the cases the π–π stacking interactions caused reorganization of hydrogen bonds and induced creation of the expected...
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Fatty acids as molecular carriers in cleavable antifungal conjugates
PublikacjaConjugates 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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Electron-Induced Decomposition of 5-Bromo-4-thiouracil and 5-Bromo-4-thio-2′-deoxyuridine: The Effect of the Deoxyribose Moiety on Dissociative Electron Attachment
PublikacjaWhen modified uridine derivatives are incorporated into DNA, radical species may form that cause DNA damage. This category of molecules has been proposed as radiosensitizers and is currently being researched. Here, we study electron attachment to 5-bromo-4-thiouracil (BrSU), a uracil derivative, and 5-bromo-4-thio-20 -deoxyuridine (BrSdU), with an attached deoxyribose moiety via the N-glycosidic (N1-C) bond. Quadrupole mass spectrometry...
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Dissociative Electron Attachment to 5-Iodo-4-thio-2′-deoxyuridine: A Potential Radiosensitizer of Hypoxic Cells
PublikacjaIn the search for effective radiosensitizers for tumor cells, halogenated uracils have attracted more attention due to their large cross section for dissociation upon the attachment of low-energy electrons. In this study, we investigated dissociative electron attachment (DEA) to 5-iodo-4-thio-2'-deoxyuridine, a potential radiosensitizer using a crossed electron-molecule beam experiment coupled with quadrupole mass spectrometry....
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Chalcogen bonding interactions in a series of aromatic selenocyanates
PublikacjaSelenium atoms in aromatic selenocyanates are characterized by the occurrence of two σ-holes, a stronger one in the prolongation of the NC–Se bond and a weaker one in the prolongation of the Ar–Se bond. The crystal structures of several bis(selenocyanato) derivatives, prepared by a method originally developed for ortho bis-substituted derivatives, illustrate very well this difference, with a short NC–Se⋯NC ChB interaction organizing...
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A Novel [4+2] Cycloaddition Reaction Involving Lawesson’s Reagent. Structure and Specific Fragmentations of a New Cyclic 1,2-Thiaphosphinane-4-one
PublikacjaA crude morpholine enamine of acetone treated with Lawesson’s reagent unexpectedly yielded a six-membered thiaphosphinane-4-one. This compound is the first example of a new class of heterocycles. It has been proven that it is formed from 4-methyl-2-morpholino-1,3-pentadiene which is usually present in crude morpholine enamine batches. A mechanism of this regioselective reaction was postulated and a characteristic chair-like conformation...
Rok 2022
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Wykorzystanie wiązań niekowalencyjnych do otrzymywania jedno- i dwuskładnikowych struktur supramolekularnych
PublikacjaPrzedstawiona rozprawa doktorska dotyczy badań nad wykorzystaniem oddziaływań międzycząsteczkowych do projektowania i syntezy uporządkowanych struktur krystalicznych, ze szczególnym uwzględnieniem wiązań halogenowych i chalkogenowych jako stosunkowo nowych i bardzo atrakcyjnych z punktu widzenia inżynierii kryształu. Praca podzielona jest na kilka części. Pierwsza z nich stanowi wstęp teoretyczny obejmujący opis, założenia oraz...
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Topochemical, Single‐Crystal‐to‐Single‐Crystal [2+2] Photocycloadditions Driven by Chalcogen‐Bonding Interactions
PublikacjaThe 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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Tetrahydroquinolinone derivatives exert antiproliferative effect on lung cancer cells through apoptosis induction
PublikacjaThe anticancer properties of quinolones is a topic of interest among researchers in the scientific world. Because these compounds do not cause side effects, unlike the commonly used cytostatics, they are considered a promising source of new anticancer drugs. In this work, we designed a brief synthetic pathway and obtained a series of novel 8-phenyltetrahydroquinolinone derivatives functionalized with benzyl-type moieties at position...