OPEN Repository

Welcome to OPEN - the Repository of Open Scientific Publications, run by the Interdisciplinary Centre for Mathematical and Computational Modelling, University of Warsaw, previously operating as the CeON Repository. The Repository enables Polish researchers from all fields to openly share their articles, books, conference materials, reports, doctoral theses, and other scientific texts.

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22799 archived items

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Evaluation of Antibacterial Activity against Nosocomial Pathogens of an Enzymatically Derived α-Aminophosphonates Possessing Coumarin Scaffold
(MDPI, 2023) Kowalczyk, Paweł; Koszelewski, Dominik; Brodzka, Anna; Kramkowski, Karol; Ostaszewski, Ryszard; Holban, Alina-Maria; Institute of Organic Chemistry, Polish Academy of Sciences; Department of Animal Nutrition, The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciences; Department of Physical Chemistry, Medical University of Bialystok
The purpose of the present study was to evaluate the synergistic effect of two important pharmacophores, coumarin and α-amino dimethyl phosphonate moieties, on antimicrobial activity against selected strains of multidrug-resistant nosocomial pathogenic bacteria. The previously developed enzyme-catalysed Kabachnik–Fields protocol allowed us to obtain the studied compounds with high yields which were free from metal impurities. The structure–activity relationship revealed that inhibitory activity is strongly related to the presence of the trifluoromethyl group (CF3−) in the coumarin scaffold. MIC and MBC studies carried out on six selected pathogenic bacterial strains (Gram-positive pathogenic Staphylococcus aureus (ATCC 23235) strain, as well as on Gram-negative Acinetobacter baumannii (ATCC 17978), Pseudomonas aeruginosa (ATCC 15442), Enterobacter cloacae (ATCC 49141), Porphyromonas gingivalis (ATCC 33277), and Treponema denticola (ATCC 35405)) have shown that tested compounds show a strong bactericidal effect at low concentrations. Among all agents investigated, five exhibit higher antimicrobial activity than those observed for commonly used antibiotics. It should be noted that all the compounds tested showed very high activity against S. aureus, which is the main source of nosocomial infections that cause numerous fatalities. Furthermore, we have shown that the studied coumarin-based α-aminophosphonates, depending on their structural characteristics, are non-selective and act efficiently against various Gram-positive and Gram-negative pathogens, which is of great importance for hospitalised patients.
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Enzymatic Synthesis of a Novel Coumarin Aminophosphonates: Antibacterial Effects and Oxidative Stress Modulation on Selected E. coli Strains
(MDPI, 2023) Koszelewski, Dominik; Kowalczyk, Paweł; Brodzka, Anna; Hrunyk, Anastasiia; Kramkowski, Karol; Ostaszewski, Ryszard; Fernández-García, Marta; Institute of Organic Chemistry, Polish Academy of Sciences; Department of Animal Nutrition, The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciences; Department of Physical Chemistry, Medical University of Bialystok
The objective of the present study was to evaluate the synergistic effect of two important pharmacophores, coumarin and -amino dimethyl phosphonate moieties, on antimicrobial activity toward selected LPS-varied E. coli strains. Studied antimicrobial agents were prepared via a Kabachnik–Fields reaction promoted by lipases. The products were provided with an excellent yield (up to 92%) under mild, solvent- and metal-free conditions. A preliminary exploration of coumarin -amino dimethyl phosphonate analogs as novel antimicrobial agents was carried out to determine the basic features of the structure responsible for the observed biological activity. The structure–activity relationship revealed that an inhibitory activity of the synthesized compounds is strongly related to the type of the substituents located in the phenyl ring. The collected data demonstrated that coumarin-based -aminophosphonates can be potential antimicrobial drug candidates, which is particularly crucial due to the constantly increasing resistance of bacteria to commonly used antibiotics.
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Chitosan with Natural Additives as a Potential Food Packaging
(MDPI, 2023-02-14) Stefanowska, Karolina; Woźniak, Magdalena; Dobrucka, Renata; Ratajczak, Izabela; Department of Chemistry, Faculty of Forestry and Wood Technology, Poznań University of Life Sciences, Poznań, Poland; Department of Industrial Products and Packaging Quality, Institute of Quality Science, Poznań University of Economics and Business, Poznań, Poland
Recently, the development of materials based on natural polymers have been observed. This is the result of increasing environmental degradation, as well as increased awareness and consumer expectations. Many industries, especially the packaging industry, face challenges resulting from legal regulations. Chitin is the most common biopolymer right after cellulose and is used to produce chitosan. Due to the properties of chitosan, such as non-toxicity, biocompatibility, as well as antimicrobial properties, chitosan-based materials are used in many industries. Many studies have been conducted to determine the suitability of chitosan materials as food packaging, and their advantages and limitations have been identified. Thanks to the possibility of modifying the chitosan matrix by using natural additives, it is possible to strengthen the antioxidant and antimicrobial activity of chitosan films, which means that, in the near future, chitosan-based materials will be a more environmentally friendly alternative to the plastic packaging used so far. The article presents literature data on the most commonly used natural additives, such as essential oils, plant extracts, or polysaccharides, and their effects on antimicrobial, antioxidant, mechanical, barrier, and optical properties. The application of chitosan as a natural biopolymer in food packaging extends the shelf life of various food products while simultaneously reducing the use of synthetic plastics, which in turn will have a positive impact on the natural environment. However, further research on chitosan and its combinations with various materials is still needed to extent the application of chitosan in food packaging and bring its application to industrial levels.
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Synthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones
(MDPI, 2023) Koszelewski, Dominik; Kowalczyk, Paweł; Samsonowicz-Górski, Jan; Hrunyk, Anastasiia; Brodzka, Anna; Łęcka, Justyna; Kramkowski, Karol; Ostaszewski, Ryszard; Hadjikakou, Sotiris K.; Institute of Organic Chemistry, Polish Academy of Sciences; Department of Animal Nutrition, The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciences; Department of Physical Chemistry, Medical University of Bialystok
A mild and efficient protocol for the synthesis of p-quinols under aqueous conditions was developed. The pivotal role of additives in the copper-catalyzed addition of aryl boronic and heteroaryl boronic acids to benzoquinones was observed. It was found that polyvinylpyrrolidone (PVP) was the most efficient additive used for the studied reaction. The noteworthy advantages of this procedure include its broad substrate scope, high yields up to 91%, atom economy, and usage of readily available starting materials. Another benefit of this method is the reusability of the catalytic system up to four times. Further, the obtained p-quinols were characterized on the basis of their antimicrobial activities against E. coli. Antimicrobial activity was further compared with the corresponding 4-benzoquinones and 4-hydroquinones. Among tested compounds, seven derivatives showed an antimicrobial activity profile similar to that observed for commonly used antibiotics such as ciprofloxacin, bleomycin, and cloxacillin. In addition, the obtained p-quinols constitute a suitable platform for further modifications, allowing for a convenient change in their biological activity profile.
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Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates
(MDPI, 2022) Samsonowicz-Górski, Jan; Koszelewski, Dominik; Kowalczyk, Paweł; Śmigielski, Paweł; Hrunyk, Anastasiia; Kramkowski, Karol; Wypych, Aleksandra; Szymczak, Mateusz; Lizut, Rafał; Ostaszewski, Ryszard; Vereshchagin, Anatoly N.; Institute of Organic Chemistry, Polish Academy of Sciences; Department of Animal Nutrition, The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciences; Department of Physical Chemistry, Medical University of Bialystok; Centre for Modern Interdisciplinary Technologies, Nicolaus Copernicus University, Toruń; Department of Molecular Virology, Institute of Microbiology, Faculty of Biology, University of Warsaw; Institute of Mathematics, Informatics and Landscape Architecture, The John Paul II Catholic University of Lublin
An enzymatic route for phosphorous–carbon bond formation was developed by discovering new promiscuous activity of lipase. We reported a new metal-free biocatalytic method for the synthesis of pharmacologically relevant β-phosphonomalononitriles via a lipase-catalyzed one-pot Knoevenagel–phospha–Michael reaction. We carefully analyzed the best conditions for the given reaction: the type of enzyme, temperature, and type of solvent. A series of target compounds was synthesized, with yields ranging from 43% to 93% by enzymatic reaction with Candida cylindracea (CcL) lipase as recyclable and, a few times, reusable catalyst. The advantages of this protocol are excellent yields, mild reaction conditions, low costs, and sustainability. The applicability of the same catalyst in the synthesis of β-phosphononitriles is also described. Further, the obtained compounds were validated as new potential antimicrobial agents with characteristic E. coli bacterial strains. The pivotal role of such a group of phosphonate derivatives on inhibitory activity against selected pathogenic E. coli strains was revealed. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics. The impact of the β-phosphono malonate chemical structure on antimicrobial activity was demonstrated. The crucial role of the substituents attached to the aromatic ring on the inhibitory action against selected pathogenic E. coli strains was revealed. Among tested compounds, four β-phosphonate derivatives showed an antimicrobial activity profile similar to that obtained with currently used antibiotics such as ciprofloxacin, bleomycin, and cloxacillin. In addition, the obtained compounds constitute a convenient platform for further chemical functionalization, allowing for a convenient change in their biological activity profile. It should also be noted that the cost of the compounds obtained is low, which may be an attractive alternative to the currently used antimicrobial agents. The observed results are especially important because of the increasing resistance of bacteria to various drugs and antibiotics.