Search results for: ACTIVE COMPOUNDS
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Glutathione-mediated conjugation of anticancer drugs: an overview of reaction mechanisms and biological significance for drug detoxification and bioactivation.
PublicationThe effectiveness of many anticancer drugs depends on the creation of specific metabolites that may alter their therapeutic or toxic properties. One significant route of biotransformation is a conjugation of electrophilic compounds with reduced glutathione, which can be non-enzymatic and/or catalyzed by glutathione-dependent enzymes. Glutathione usually combines with anticancer drugs and/or their metabolites to form more polar...
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Understanding the origin of high corrosion inhibition efficiency of bee products towards aluminium alloys in alkaline environments
PublicationVarious bee products were found to be efficient corrosion inhibitors of aluminium in different environments. In particular, bee pollen was found to be highly effective in alkaline electrolytes, yet its highly complex composition and possible synergistic interactions hinder determination of the compounds acting as active corrosion inhibitors. The main purpose of the following work is to investigate the effect of solvents used for...
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Photosensitive and pH-dependent activity of pyrazine-functionalized carbazole derivative as promising antifungal and imaging agent
PublicationCarbazole skeleton plays a significant role as a structural scaffold of many pharmacologically active compounds. Pyrazine-functionalized carbazole derivative was constructed by coupling 2-amino-5-bromo-3-methylaminepyrazine (ABMAP) into 3 and 6 positions of the carbazole ring. Multi-experimental methods were used, e.g., potentiometric, spectroscopic (ATR, UV, XRD powder,1H and13C NMR), electrochemical (cyclic voltammetry), and...
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From tryptophan to novel mitochondria-disruptive agent, synthesis and biological evaluation of 1,2,3,6-tetrasubstituted carbazoles
PublicationMitochondrial targeting plays an important role in anticancer therapy. The Mn(III)-promoted cyclization of 5- (1H-indol-3-yl)-3-oxopentanoic acid allow to obtain novel substituted carbazole derivatives that can act as mitochondria-disruptive agents. The starting materials used for the synthesis of these new aminocarbazoles are oxopentanoate derivatives of tryptophan. The scope and limitation of this method of synthesis are determined...
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Family Tree for Aqueous Organic Redox Couples for Redox Flow Battery Electrolytes: A Conceptual Review
PublicationRedox flow batteries (RFBs) are an increasingly attractive option for renewable energy storage, thus providing flexibility for the supply of electrical energy. In recent years, research in this type of battery storage has been shifted from metal-ion based electrolytes to soluble organic redox-active compounds. Aqueous-based organic electrolytes are considered as more promising electrolytes to achieve “green”, safe, and low-cost...
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Personalized nutrition in ageing society: redox control of major-age related diseases through the NutRedOx Network (COST Action CA16112)
PublicationA healthy ageing process is important when it is considered that one-third of the population of Europe is already over 50 years old, although there are regional variations. This proportion is likely to increase in the future, and maintenance of vitality at an older age is not only an important measure of the quality of life but also key to participation and productivity. So, the binomial “nutrition and ageing” has different aspects...
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c-Myc Protein Level Affected by Unsymmetrical Bisacridines Influences Apoptosis and Senescence Induced in HCT116 Colorectal and H460 Lung Cancer Cells
PublicationUnsymmetrical bisacridines (UAs) are highly active antitumor compounds. They contain in their structure the drugs previously synthesized in our Department: C-1311 and C-1748. UAs exhibit different properties than their monomer components. They do not intercalate to dsDNA but stabilize the G-quadruplex structures, particularly those of the MYC and KRAS genes. Since MYC and KRAS are often mutated and constitutively expressed in cancer...
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Investigating the disease- modifying properties of sclerotiorin in Alzheimer's therapy using acetylcholinesterase inhibition
PublicationAlzheimer's disease (AD) is a progressive neurodegenerative disorder caused due to the damage and loss of neurons in specific brain regions. It is the most common form of dementia observed in older people. The symptoms start with memory loss and gradually cause the inability to speak and do day-to-day activities. The cost of caring for those affected individuals is huge and is probably beyond most developing countries capability....
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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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Acid–Base Equilibrium and Self-Association in Relation to High Antitumor Activity of Selected Unsymmetrical Bisacridines Established by Extensive Chemometric Analysis
PublicationUnsymmetrical bisacridines (UAs) represent a novel class of anticancer agents previously synthesized by our group. Our recent studies have demonstrated their high antitumor potential against multiple cancer cell lines and human tumor xenografts in nude mice. At the cellular level, these compounds affected 3D cancer spheroid growth and their cellular uptake was selectively modulated by quantum dots. UAs were shown to undergo metabolic...
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Potential of Silver Nanoparticles in Overcoming the Intrinsic Resistance of Pseudomonas aeruginosa to Secondary Metabolites from Carnivorous Plants
PublicationCarnivorous plants are exemplary natural sources of secondary metabolites with biological activity. However, the therapeutic antimicrobial potential of these compounds is limited due to intrinsic resistance of selected bacterial pathogens, among which Pseudomonas aeruginosa represents an extreme example. The objective of the study was to overcome the intrinsic resistance of P. aeruginosa by combining silver nanoparticles (AgNPs)...
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The chemistry of river–lake systems in the context of permafrost occurrence (Mongolia, Valley of the Lakes) Part II. Spatial trends and possible sources of organic composition
PublicationThe chemistry of river–lake systems located in Central Mongolia near the southern border of permafrost occurrence has not been well studied. The main aim of this paper is to summarize patterns in water chemistry in supply springs, rivers and lakes in relation to permafrost occurrence, as well as other natural and anthropogenic impacts. The analyses involved water samples taken from two river–lake systems: the Baydrag River–Böön...
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The Distribution of Glucosinolates in Different Phenotypes of Lepidium peruvianum and Their Role as Acetyl- and Butyrylcholinesterase Inhibitors—In Silico and In Vitro Studies
PublicationThe aim of the study was to present the fingerprint of different Lepidium peruvianum tu- ber extracts showing glucosinolates-containing substances possibly playing an important role in preventinting dementia and other memory disorders. Different phenotypes of Lepidium peruvianum (Brassicaceae) tubers were analysed for their glucosinolate profile using a liquid chromatograph coupled with mass spectrometer (HPLC-ESI-QTOF-MS/MS platform)....
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Release systems based on self-assembling RADA16-I hydrogels with a signal sequence which improves wound healing processes
PublicationSelf-assembling peptides can be used for the regeneration of severely damaged skin. They can act as scaffolds for skin cells and as a reservoir of active compounds, to accelerate scarless wound healing. To overcome repeated administration of peptides which accelerate healing, we report development of three new peptide biomaterials based on the RADA16-I hydrogel functionalized with a sequence (AAPV) cleaved by human neutrophil elastase...
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Synthesis of 3-(2-Alkylthio-4-chloro-5-methylbenzenesulfonyl)-2-(1-phenyl-3-arylprop-2-enylideneamino)guanidine Derivatives with Pro-Apoptotic Activity against Cancer Cells
PublicationThe untypical course of reaction between chalcones and benzenesulfonylaminoguanidines led to the new 3-(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-2-(1-phenyl-3-arylprop-2- enylideneamino)guanidine derivatives 8–33. The new compounds were tested in vitro for their impact on the growth of breast cancer cells MCF-7, cervical cancer cells HeLa and colon cancer cells HCT-116 by MTT assay. The results revealed that the activity of...
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Biochemical, Structural Analysis, and Docking Studies of Spiropyrazoline Derivatives
PublicationIn this study, we evaluated the antiproliferative potential, DNA damage, crystal struc‐ tures, and docking calculation of two spiropyrazoline derivatives. The main focus of the research was to evaluate the antiproliferative potential of synthesized compounds towards eight cancer cell lines. Compound I demonstrated promising antiproliferative properties, especially toward the HL60 cell line, for which IC50 was equal to 9.4 μM/L....
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Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N'-(2-arylmethylthio-4-chloro-5- methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII
PublicationA series of novel N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines 9 e41 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and cancer-associated isozymes CA IX and XII. Against the human CA I investigated compounds showed KI in the range of 87e6506 nM, toward hCA II ranging from 7.8 to 4500 nM,...
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A new 1-nitro-9-aminoacridine derivative targeting yeast topoisomerase II able to overcome fluconazole-resistance
PublicationFungal resistance remains a significant threat and a leading cause of death worldwide. Thus, overcoming microbial infections have again become a serious clinical problem. Although acridine derivatives are widely analyzed as anticancer agents, only a few reports have demonstrated their antifungal activity. In an effort to develop biologically active antifungals, twelve novel C-857 (9-(2′ -hydroxyethylamino)-1-nitroacridine) and...
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9,10-Dioxoanthracenyldithiocarbamates effectively inhibit the proliferation of non-small cell lung cancer by targeting multiple protein tyrosine kinases
PublicationAnthraquinones have attracted considerable interest in the realm of cancer treatment owing to their potent anticancer properties. This study evaluates the potential of a series of new anthraquinone derivatives as anticancer agents for non-small-cell lung cancer (NSCLC). The compounds were subjected to a range of tests to assess their cytotoxic and apoptotic properties, ability to inhibit colony formation, pro-DNA damage functions,...
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SURFACTANTS IN KLODNICA RIVER (KATOWICE, POLAND). PART I. LINEAR ALKYLBENZENE SULPHONATES (LAS)
PublicationSurfactants are a group of compounds with specific physico-chemical properties and therefore they are used in many spheres of human activity. Surface-active substances undergo various physico-chemical transformations, what enables their migration between different elements of the environment and may lead to its pollution. Selected anionic surfactants were determined in samples of water from the Klodnica river (25 samples) and bottom...
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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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Hybrid electrode materials for fast performance devices
PublicationEnergy storage devices such as Electrochemical Double Layer Capacitors and other types of the electrochemical capacitors require chemically stable, non-soluble, electrochemically active electrode materials compatible with appropriate electrolytes. Factors which determine their applicability are derived from so called electrochemical window of electroltes, nature of charge accumulation and their kinetics. On the other hand technological...
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Metabolic transformation of antitumor acridinone C-1305 but not C-1311 via selective cellular expression of UGT1A10 increases cytotoxic response: implications for clinical use.
PublicationThe acridinone derivates C-1305 and C-1311 are promising antitumor agents with high activity against several experimental cellular and tumor models and which are under evaluation in pre-clinical and early phase clinical trials. Recent evidence from our laboratories has indicated that both compounds were conjugated by several UGT isoforms with the most active being extrahepatic UGT1A10. The present studies were designed to test...
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Photocatalytic degradation and pollutant-oriented structure-activity analysis of carbamazepine, ibuprofen and acetaminophen over faceted TiO2
PublicationPhotocatalytic degradation of carbamazepine, ibuprofen, acetaminophen and phenol was studied in the presence of anatase photocatalyst, exposing three different crystal facets in the majority of {0 0 1}, {1 0 0} or {1 0 1}. It was found that octahedral anatase particles exposing {1 0 1} facets allow to achieve the best degradation and mineralization of all persistent organic pollutants. This confirms that the previous findings,...
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Synthesis of functionalized new conjugates of batracylin with tuftsin/ retro-tuftsin derivatives and their biological evaluation
PublicationNew batracylin conjugates with tuftsin/retro-tuftsin derivatives were designed and synthesized using T3P as a coupling agent. The conjugates possess an amide bond formed between the carboxyl group of heterocyclic molecule and the N-termini of the tuftsin/retro-tuftsin chain. The in vitro cytotoxic activity of the new analogues and their precursors was evaluated using a series of human and murine tumor cells. BAT conjugates containing...
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Dietary antioxidants as a source of hydrogen peroxide
PublicationStudies of 54 antioxidants revealed that 27 of them, mainly polyphenols, generated hydrogen peroxide (H2O2) when added to Dulbecco’s modified Eagle’s medium (DMEM), other media used for culture of mammalian and yeast cells and phosphate-buffered saline. The most active antioxidants were: propyl gallate (PG), (−)-epigallocatechin gallate (EGCG) and quercetin (Q). Chelex treatment and iron chelators decreased H2O2 generation suggesting...
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Voriconazole-Based Salts Are Active against Multidrug-Resistant Human Pathogenic Yeasts
PublicationVoriconazole (VOR) hydrochloride is unequivocally converted into VOR lactates and valinates upon reaction with silver salts of organic acids. This study found that the anticandidal in vitro activity of these compounds was comparable or slightly better than that of VOR. The Candida albicans clinical isolate overexpressing CaCDR1/CaCDR2 genes, highly resistant to VOR, was apparently more susceptible to VOR salts. On the other hand,...
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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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Biosynthetic and synthetic access to amino sugars.
PublicationAmino sugars are important constituents of a number of biomacromolecules and products of mi crobial secondary metabolism, including antibiotics. For most of them, the amino group is located at the positions C1, C2 or C3 of the hexose or pentose ring. In biological systems, amino sugars are formed due to the catalytic activity of specific aminotransferases or amidotransferases by introducing an amino functionality derived from L-glutamate...
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Analytical studies on the environmental state of the Svalbard archipelago - critical source of information about anthropogenic global impact
PublicationThe Svalbard archipelago differs from other polar regions due to its specific environmental conditions and geographic location which make the area gather pollution from long-range transport. Due to the recent development in analytical techniques it is possible to determine the concentration of pollutants at the level present there. This paper collates and discusses the information from the literature about: pollutants present in...
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New conjugates of tuftsin and muramyl dipeptide as stimulators of human monocytes-derived dendritic cells
PublicationMuramyl dipeptide (MDP) and tuftsin are known biologically active compound displaying a significant influence on various cell populations of innate immune response. MDP, as a fragment of bacterial cell wall, stimulates not only macrophages and monocytes, but also dendritic cells. In contrast, little is known about tuftsin influence on these cells. Therefore it seemed vital to access whether tuftsin or its derivatives conjugated...
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The Interplay between Endogenous and Foodborne Pro-Oxidants and Antioxidants in Shaping Redox Homeostasis
PublicationOxidative stress has been known about in biological sciences for several decades; however, the understanding of this concept has evolved greatly since its foundation. Over the past years, reactive oxygen species, once viewed as solely deleterious, have become recognized as intrinsic components of life. In contrast, antioxidants, initially believed to be cure-all remedies, have failed to prove their efficacy in clinical trials....
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Peptide conjugates of lactoferricin analogues and antimicrobials—Design, chemical synthesis, evaluation of antimicrobial activity and mammalian cytotoxicity
PublicationEight new peptide conjugates composed of modified bovine lactoferricin truncated analogues (LFcinB) and oneof the three antimicrobials — ciprofloxacin (CIP), levofloxacin (LVX), and fluconazole (FLC) — were synthesized. Four different linkers were applied to connect a peptide and an antimicrobial agent. The FLC-containing peptidic conjugates were synthesized using the “click chemistry” method. This novel approach is reported here...
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Mapping the Structural and Dynamic Determinants of pH-Sensitive Heparin Binding to Granulocyte Macrophage Colony Stimulating Factor
PublicationGranulocyte macrophage colony stimulating factor (GMCSF) is an immunomodulatory cytokine that is harnessed as a therapeutic. GMCSF is known to interact with other clinically important molecules, such as heparin, suggesting that endogenous and administered GMCSF has the potential to modulate orthogonal treatment outcomes. Thus, molecular level characterization of GMCSF and its interactions with biologically active compounds is critical...
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Effective Drug Concentration and Selectivity Depends on Fraction of Primitive Cells
PublicationPoor efficiency of chemotherapeutics in the eradication of Cancer Stem Cells (CSCs) has been driving the search for more active and specific compounds. In this work, we show how cell density-dependent stage culture profiles can be used in drug development workflows to achieve more robust drug activity (IC50 and EC50) results. Using flow cytometry and light microscopy, we characterized the cytological stage profiles of the HL-60-,...
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Teloxantron inhibits the processivity of telomerase with preferential DNA damage on telomeres
PublicationTelomerase reactivation is one of the hallmarks of cancer, which plays an important role in cellular immortalization and the development and progression of the tumor. Chemical telomerase inhibitors have been shown to trigger replicative senescence and apoptotic cell death both in vitro and in vivo. Due to its upregulation in various cancers, telomerase is considered a potential target in cancer therapy. In this study, we identified...
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Relationship between the betalain composition in Opuntia ficus indica and Beta vulgaris varieties and biological activity of their extracts
PublicationBetalains are a class of pigments that are much less com- monly found in nature than anthocyanins or carotenoids. They occur only in a few edible plants such as red beetroot (Beta vulgaris), prickly pears (Opuntia ficus indica), amaranth (Amaranthus sp.) and some mushrooms. This group of pig- ments can be divided into two major groups: yellow vulgax- anthins and red betanins. Despite their structural similarity to compounds from...
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Recent progress in the development of steroid sulfatase inhibitors – examples of the novel and most promising compounds from the last decade
PublicationThe purpose of this review article is to provide an overview of recent achievements in the synthesis of novel steroid sulfatase (STS) inhibitors. STS is a crucial enzyme in the biosynthesis of active hormones (including estrogens and androgens) and, therefore, represents an extremely attractive molecular target for the development of hormone-dependent cancer therapies. The inhibition of STS may effectively reduce the availability...
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Electrochemical simulation of enzymatic transformations studied for the selected antitumor acridine derivatives
PublicationThe elucidation of the metabolic pathways and the biotransformation mechanisms of potential drugs is a crucial point in drug development. It allows to know the activation routes of the new biologically active compounds, especially in respect to their possible toxicity. Generally, in vivo or in vitro experiments with liver microsomes or hepatocytes are performed. However, these testing schemes are tedious, time consuming and of...
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Enabling simultaneous redox transformation of toxic chromium(VI) and arsenic(III) in aqueous media—A review
PublicationSimultaneous conversion of most harmful As(III) and Cr(VI) to their less toxic counterparts is environmentally desirable and cost-effective. It has been confirmed that simultaneous oxidation of As(III) to As(V) and reduction of Cr(VI) to Cr(III) can occur via free radical or mediated electron transfer processes. While Cr(VI) is reduced by reacting with H•, eaq−, photoelectron directly or undergoing ligand exchange with H2O2 and...
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Ipertrofan Revisited—The Proposal of the Complete Stereochemistry of Mepartricin A and B
PublicationBeing a methyl ester of partricin, the mepartricin complex is the active substance of a drug called Ipertrofan (Tricandil), which was proven to be useful in treatment of benign prostatic hyperplasia and chronic nonbacterial prostatitis/chronic pelvic pain syndrome. Nevertheless, no direct structural evidence on the stereochemistry of its components has been presented to date. In this contribution, we have conducted detailed, NMR-driven...
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Unexpected Z/E isomerism of N-methyl-O-phosphothioyl benzohydroxamic acids, their oxyphilic reactivity and inertness to amines
PublicationThiophosphinoylation of N-methyl p-substituted benzohydroxamic acids using disulfanes (method A) or diphenylphosphinothioyl chloride (method B) provides only one conformer of the respective O-phosphothioyl derivative (Xray and NMR analysis). Undergoing the P-transamidoxylation reaction is an evidence of the reversibility of thiophosphinoylation. Only those products containing strong EWG substituents in the aroyl residue or bulky...
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New Chalcones Derivatives With Potent Antitumor Activity And Their Metabolism In Vitro
PublicationChalcone derivatives exhibit a broad range of biological activities, with antioxidant and cytotoxic properties among the most studied. Despite numerous reports on chalcones as cytotoxic, and potentially anticancer agents, very little is know on their actual mechanism of activity. Generally, chalcones are considered as antimitotic agents, which interfere with tubulin assembly.We have recently developed a new class of chalcones with...
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Application of Multivariate Adaptive Regression Splines (MARSplines) Methodology for Screening of Dicarboxylic Acids Cocrystal Using 1D and 2D Molecular Descriptors
PublicationDicarboxylic acids (DiAs) are probably one of the most popular cocrystals formers. Due to the high hydrophilicity and non-toxicity, they are promising solubilizes of active pharmaceutical ingredients (APIs). Although DiAs appear to be highly capable of forming multicomponent crystals with various compounds, some systems reported in the literature are physical mixtures the solid state without forming stable intermolecular complex....
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Oxolane Ammonium Salts (Muscarine-Like)—Synthesis and Microbiological Activity
PublicationCommercially available 2-deoxy-D-ribose was used to synthesize the appropriate oxolane derivative—(2R,3S)-2-(hydroxymethyl)oxolan-3-ol—by reduction and dehydration/cyclization in an acidic aqueous solution. Its monotosyl derivative, as a result of the quaternization reaction, allowed us to obtain eight new muscarine-type derivatives containing a quaternary nitrogen atom and a hydroxyl group linked to the oxolane ring. Their structure...
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Synthesis, Molecular Structure, Anticancer Activity, and QSAR Study of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)Benzenesulfonamide Derivatives
PublicationA series of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)benzenesulfonamides were synthesized from 4-amino-N-(aryl/heteroaryl)benzenesulfonamides and 2,5-dimethoxytetrahydrofuran. All the synthesized compounds were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7 human tumor cell lines. Compound 28, bearing 8-quinolinyl moiety, exhibited the most potent anticancer activity against the HCT-116, MCF-7, and HeLa cell lines,...
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Analysis of catalitic reactors usefulness to reduce pollution generated by piston combustion engines with regard to ship main engines
PublicationThe article presents results which indicate that the use of catalytic reactors to reduce emissions of harmful compunds contained in the exhaust gas is important in the operation of vehicle motors operation. Efforts of the shipbuilding industry to reduce the toxicity of exhaust gas emitted by the main engines have been indicated and pointed to the desirability of the use of these catalysts in maritime transport. It has been pointed...
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Poszukiwanie nowych leków immunosupresyjnych (Quest for new immunosuppressive drugs)
PublicationTransplantology is getting more and more important in medicine. Development of surgical techniques and immunosuppressive treatment enabled to establish successful transplantations with various organs and tissues. However, allografts are recognized as foreign tissues and stimulate rejection, i.e. a strong immunological response which, if not stopped, results in complete destruction of the transplanted tissue. In order to prevent...
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In Silico Safety Assessment of Bacillus Isolated from Polish Bee Pollen and Bee Bread as Novel Probiotic Candidates
PublicationBacillus species isolated from Polish bee pollen (BP) and bee bread (BB) were characterized for in silico probiotic and safety attributes. A probiogenomics approach was used, and in-depth genomic analysis was performed using a wide array of bioinformatics tools to investigate the presence of virulence and antibiotic resistance properties, mobile genetic elements, and secondary metabolites. Functional annotation and Carbohydrate-Active...
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Protection and viability of fruit seeds oils by nanostructured lipid carrier (NLC) nanosuspensions
PublicationIn this paper, we focused on the development of nanostructured lipid carriers (NLCs) for dermal application. The NLC matrix was designed as a protective reservoir of biological active compounds that naturally occur in domestic fruit seed oils. Over the years, emulsions, as a popular physicochemical form of personal care products, were refined in order to obtain the best possible penetration into the skin of any bioactive compound...