2016 - Repozytorium publikacji - Politechnika Gdańska

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Synthesis and biological evaluation of fluorinated 3-phenylcoumarin-7-O-sulfamate derivatives as steroid sulfatase inhibitors
- Sebastian Demkowicz
- Mateusz Daśko
- Witold Kozak
- Katarzyna Krawczyk
- Dariusz Witt
- Maciej Masłyk
- Konrad Kubiński
- Janusz Rachoń
2016 Chemical Biology & Drug Design
In the present work, we report the initial results of our study on a series of 3-phenylcoumarin sulfamate-based compounds containing C-F bonds as a novel inhibitors of steroid sulfatase (STS). The new compounds are potent STS inhibitors, possessing more than 10 times higher inhibitory potency than coumarin-7-O-sulfamate. In the course of our investigation, compounds 2b and 2c demonstrated the highest inhibitory effect in the enzymatic STS assay; both had IC50 values of 0.27 μM (the IC50 value of coumarin-7-O-sulfamate is 3.5 μM, used as a reference).
Synthesis and biological evaluation of novel analogues of batracylin with synthetic amino acids and adenosine: an unexpected effect on centromere segregation in tumor cells through a dual inhibition of topoisomerase IIa and Aurora B
- Wioleta Januchta
- Marcin Serocki
- Krystyna Dzierzbicka
- Grzegorz Cholewiński
- Monika Gensicka-Kowalewska
- Andrzej Składanowski
2016 Pełny tekst RSC Advances
In the search for new anticancer agents we designed and synthesized batracylin derivatives with linking synthetic amino acid side chains of different lengths and adenosine. Unexpectedly, we have found that in water and the culture media adenosine–amino acid–BAT conjugates form supramolecular structures and this prevents these compounds from entering cells. Consequently, these compounds exerted no biological activity when tested towards two human cell lines, lung adenocarcinoma (A549) and human leukemia (HL-60). In contrast, several amino acid–BAT precursors showed up to 25-fold enhanced cytotoxic activity compared to BAT and these compounds strongly interfered with DNA topoisomerase II activity and its cellular functions. In particular, these conjugates inhibited centromere segregation during mitosis in drug-treated tumor cells by preventing topoisomerase II-dependent Aurora B activation.
Synthesis and characterisation of polyurethane elastomers with semi-products obtained from polyurethane recycling
- Patrycja Jutrzenka Trzebiatowska
- Tamara Calvo-Correas
- Arantxa Eceiza
- Janusz Datta
2016 Pełny tekst EUROPEAN POLYMER JOURNAL
In this work polyurethane elastomers were synthesised by using different mixtures of a petrochemical and glycerolysate polyols and 4,4-diphenylmethane diisocyanate (MDI). Glycerolysate polyol was produced from polyurethane foam decomposition using crude glycerine as a decomposition agent. The structure and thermal properties of obtained semi-product were similar to the polyol used in the synthesis of original foam. Glycerolysate polyol was incorporated into polyurethane formulation as soft segment (SS). Since polyol is one of the major component in polyurethane system (>70%) introducing recycled components leads to lowering of consumption of petrochemicals and valorisation of recycled products. Polyurethane elastomers containing up to 16.4 wt.% of glycerolysate polyol were synthesised, soluble in dimethylformamide (DMF) up to ca. 12 wt.%. The effect of glycerolysate polyol content on the structure and properties was analysed by Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), dynamic mechanical analysis (DMA) and mechanical tests. Thermal properties did not worsen after using glycerolysate into polyurethane formulation. A slight increase in glass transition temperature is observed with the incorporation of glycerolysate polyol. Elastic modulus, tensile strength and hardness of polyurethane elastomers increased with recycled polyol content. Moreover they showed high elongation at break values.
Synthesis and Characterization of Monometallic (Ag, Cu) and Bimetallic Ag-Cu Particles for Antibacterial and Antifungal Applications
- Marta Paszkiewicz
- Anna Gołąbiewska
- Łukasz Rajski
- Ewelina Kowal
- Agnieszka Sajdak
- Adriana Zaleska-Medynska
- Anna Golabiewska
2016 Pełny tekst Journal of Nanomaterials
In this paper, the experimental studies are concerned with the effect of the synthesis parameters on the formation of monometallic Ag and Cu nanoparticles (NPs). We consider the synthesis strategies verification for the bimetallic core-shell and alloy particles preparation. It was successfully obtained by chemical reduction method. The obtained colloidal solution is characterized by the transmission electron microscopy (TEM) with energy-dispersive X-ray spectroscopy (EDX) data, UV-Vis spectra, particle size distribution, and zeta potential. This work presents a comprehensive overview of experimental studies of the most stable colloidal solutions to impregnate fabrics that will exhibit a bactericidal and fungicidal activity against Candida albicans, Escherichia coli, and Staphylococcus aureus
Synthesis and characterization of ruthenium and rhenium dyes with phosphonate anchoring groups
- Markus Braumüller
- Martin Schulz
- Magdalena Staniszewska
- Dieter Sorsche
- Markus Wunderlin
- Jürgen Popp
- Julien Guthmuller
- Benjamin Dietzek
- Sven Rau
2016 DALTON TRANSACTIONS
Re(L1)–Re(L3), a series of rhenium(I) tricarbonyl chloride complexes with bpy-R2 derivatives L1–L3 (bpy = 2,2′-bipyridine, R represents the substitution at the 4- and 4′-positions), and their corresponding trishomoleptic Ru(L1)3–Ru(L3)3 as well as heteroleptic ruthenium(II) complexes Ru(tbbpy)2(L1) and Ru(tbbpy)2(L2) have been synthesized and characterized. Their applicability as immobilizable metal–organic chromophores in solar and photosynthesis cells is enabled by R, since it includes phosphonic ester groups as precursors for potent phosphonate anchoring groups. Conjugated linkers (phenylene and triazole moieties) serve as distance control between bpy and the anchor. Photophysical and electrochemical studies reveal pronounced effects of the aryl substitution. These effects were further investigated using resonance Raman experiments and supported by theoretical calculations. After hydrolysis the triazole containing Re(L2) was successfully immobilized on NiO, suggesting that its application in photovoltaic cells is feasible. The solid state structures of Re(L0), Re(L0hydrolyzed), Re(L1) and Re(L2) are reported in this paper, enabling the determination of the distances and intermolecular interactions.
Synthesis and photoelectrochemical behaviour of hydrogenated titania nanotubes modified with conducting polymer infiltrated by redox active network
- Katarzyna Siuzdak
- Mariusz Szkoda
- Jakub Karczewski
- Jacek Ryl
- Anna Lisowska-Oleksiak
2016 ELECTROCHIMICA ACTA
In this work, we show preparation of ordered inorganic-organic composite electrode material where hydrogenated titania nanotubes H-TiO2 with tubularly developed surface modified with poly(3,4-ethylenedioxythiophene) matrix permeated by Prussian Blue (PB) inorganic redox network in order to reach highly photoactive heterojunction. The polymer deposition was realized via two subsequent processes covering: i) potentiostatic polymerization carried out at H-TiO2 electrode immersed in solution of EDOT monomer and Fe[(CN)6]3−/4− ions and ii) cyclic voltammetry routs in iron chloride solution. The inorganic-organic hybrids were characterized by scanning electron microscopy, spectroscopic techniques (UV-Vis, Raman, Fourier transform infrared and X-ray photoelectron spectroscopy) and using electrochemical methods. Cyclic voltammetry curves registered for inorganic-organic composite exhibit clear reversible reduction/oxidation peaks attributed to the high spin (HS) FeII/FeIII redox activity when low spin (LS) FeII/FeIII redox activity overlaps with the water oxidation process. The LS FeII/FeIII redox center of PB imbedded in pEDOT matrix plays crucial role in high increase of photocurrent recorded for composite H-TiO2NTs/pEDOT:BP that is 3.7 times higher in comparison to photocurrent measured for H-TiO2NT at anodic polarization of electrode.
Synthesis and properties of carboxy derivative of Epidian 6 monomethacrylate (in English)
- Mykhailo Bratychak
- Ostap Iatsyshyn
- Piotr Bruździak
- Jacek Namieśnik
- O. Shyshchak
2016 Pełny tekst Polimery
We present the synthesis of an oligomer with carboxy and methacrylic groups based on Epidian 6. The effect of the catalyst nature and amount, solvent nature and process temperature on the rate of the reaction between Epidian6 monomethacrylate and adipic acid was examined at 313, 323 and 333 K in the presence of 4-dimethylaminopyridine, 1,4-diazobicyclo[2.2.2]octane, and benzyltriammonium chloride. The synthesized oligomer was characterized using chemical and IR-spectroscopic analyses. We suggest the use of the synthesized product as an active additive to epoxy-oligoesteric blends based on Epidian 5. The chemistry of the film forming process has been determined using IR-spectroscopy.
Synthesis and properties of new 'N,'N-phenyltetrazole podand
- Agnieszka Pazik
- Beata Kamińska
- Anna Skwierawska
- Sandra Nakonieczna
- Tadeusz Ossowski
2016 CHEMICAL PAPERS
The synthesis of a new chromogenic N,N-phenyltetrazole receptor is reported here. The cationbinding properties of this receptor in solution were investigated by naked-eye colour change, electrochemical methods and UV-Vis spectroscopy in various solvents (CH3CN, dimethylsulphoxide (DMSO), DMSO/H2O, CH3CN/H2O and CH3CN/MeOH). In addition, the receptor was used as a sensing material in ion-selective membrane electrodes. The selectivity and sensitivity of these electrodes towards alkali, alkali-earth, transition and heavy metal cations in aqueous solution were tested. The relation between the carrier structure and membrane plasticisers was investigated.
SYNTHESIS AND PROPERTIES OF OLIGOMERS WITH HYDROXY END-GROUPS
- Ostap Ivashkiv
- Jacek Namieśnik
- Olena Shyshchak
- Polyuzhyn Igor
- Mykhailo Bratychak
2016 Pełny tekst Chemistry & Chemical Technology
Methods of oligomers (polymers) with hydroxy end-groups obtaining are examined. The synthesis of hydroxy-containing oligomers based on epoxy resins is of special attention. The molecules of mentioned oligomers apart from free primary and secondary hydroxy groups contain epoxy, peroxy, carboxy or acrylic groups.
Synthesis and steroid sulfatase inhibitory activities of N-phosphorylated 3-(4-aminophenyl)-coumarin-7-O-sulfamates
- Mateusz Daśko
- Maciej Masłyk
- Konrad Kubiński
- Justyna Aszyk
- Janusz Rachoń
- Sebastian Demkowicz
2016 MedChemComm
In the present work, we report convenient methods for the synthesis and biological evaluation of N-phosphorylated derivatives of 3-(4-aminophenyl)-coumarin-7-O-sulfamate as potential steroid sulfatase (STS) inhibitors. Their binding modes were modeled using docking techniques. The inhibitory effects of the synthesized compounds were tested on STS isolated from human placenta. All of the newly synthesised coumarin derivatives were powerful inhibitors of STS with IC50 values ranging between 0.19 and 0.78 μM. In particular, we found that 3-[4-(diphenoxy-phosphorylamino)-phenyl]-coumarin-7-O-sulfamate 10e and 3-[4-(dibenzyloxy-phosphorylamino)-phenyl]-coumarin-7-O-sulfamate 10f produced the highest inhibitory effects, with IC50 values of 0.19 and 0.24 μM, respectively (IC50 values of 1.38 μM for coumarin-7-O-sulfamate 2 and 1.03 μM for coumate 3 used as reference). The structure–activity relationships of the synthesized coumarin derivatives toward the STS enzyme were discussed.
Synthesis and structural properties of (Y, Sr)(Ti, Fe, Nb)O3−δ perovskite nanoparticles fabricated by modified polymer precursor method
- Tadeusz Miruszewski
- Paweł Gdaniec
- Jakub Karczewski
- Beata Bochentyn
- Krystyna Szaniawska
- Piotr Kupracz
- Marta Prześniak-Welenc
- Bogusław Kusz
2016 SOLID STATE SCIENCES
The yttrium, iron and niobium doped-SrTiO3 powders have been successfully fabricated by a modified low–temperature synthesis method from a polymer complex. The usage of strontium hydroxide precursor instead of conventional strontium nitrate or strontium carbonate provides to the possibility of significant decrease of annealing temperature. It allows to prepare a material with sphere-shape grains of nanometric size (15–70 nm). The results of thermal analysis indicate that the crystallization of precursor takes place at different stages. The product after heat treatment at 600 °C for 3 h in air was also characterized by X-Ray diffraction method (XRD) and Fourier transform – infrared spectroscopy (FT-IR). After the crystallization and the impurity removal process, a single-phase material was obtained in case of all analyzed samples. The morphology of obtained nano-powders was also studied by a scanning electron microscopy (SEM). It can be concluded, that this method allows obtaining a perovskite phase of a metal doped SrTiO3 with nanometric particles.
Synthesis, crystal structure and cytotoxic activity of ruthenium(II) piano-stool complex with N,N-chelating ligand
- Patrycja Rogala
- Agnieszka Jabłońska-Wawrzycka
- Katarzyna Kazimierczuk
- Agnieszka Borek
- Agnieszka Błażejczyk
- Joanna Wietrzyk
- Barbara Barszcz
2016 JOURNAL OF MOLECULAR STRUCTURE
A mononuclear compound of the general formula [(η6-p-cymene)RuIICl(2,2′-PyBIm)]PF6 has been synthesized from a bidentate N,N-donor ligand, viz. 2,-(2′-pyridyl)benzimidazole (2,2′-PyBIm) and the corresponding chloro-complex [(η6-p-cymene)Ru(μ-Cl)Cl]2 (precursor). The isolated coordination compound was characterized by IR, UV–vis and 1H, 13C NMR spectroscopies. The single crystal X-ray analysis of the complex reveals that the asymmetric part of the unit cell consists of two symmetrically independent, [(η6-p-cymene)RuCl(2,2′-PyBIm)]+ cationic complexes. Each cation exhibits a pseudo-octahedral three-legged piano-stool geometry, in which three “legs” are occupied by one chloride ion and two nitrogen donor atoms of the chelating ligand 2,2′-PyBIm. The Hirshfeld surface analysis of obtained complex was determined, too. The ionic nature of the compound is identified by a strong band at around 830 cm−1 due to the νP−F stretching mode of the PF6− counter ion. The electronic spectrum of this monomeric complex displays high intensity bands in the ultraviolet region assignable to π→π*/n→π* transitions, as well as a band attributable to the metal-to-ligand charge transfer (MLCT) dπ(Ru)→π*(L) transition. Additionally, the complex has been screened for its cytotoxicity against three human cancer lines: non-small cell lung carcinoma (A549), colon adenocarcinoma (HT29) and breast adenocarcinoma (MCF-7) as well as normal mice fibroblast cells (BALB/3T3). The complex demonstrated a moderate antiproliferative activity against the cell lines tested.
Synthesis of Combretastatin A-4 Analogs and their Biological Activities
- Agnieszka Siebert
- Monika Gensicka-Kowalewska
- Grzegorz Cholewiński
- Krystyna Dzierzbicka
2016 Pełny tekst Anti-Cancer Agents in Medicinal Chemistry
Combretastatin A-4 (CA-4) is a natural product, which consists of two phenyl rings, linked by an ethylene bridge. CA-4, inhibitor of polymerization of tubulin to microtubules, possesses a strong antitumor and anti-vascular properties both in vitro and in vivo. Previous studies showed that disodium phosphate salt of CA-4, a water-soluble prodrug is well tolerated at therapeutically useful doses. However, it should be noted that the cis-configuration of the double bond and the 3,4,5-trimethoxy group on ring A is necessary for the biological activity of CA-4. Structure of CA-4 renders the compound readily susceptible to isomerization, which reduces the potency and bioavailability. To circumvent this problem, a lot of scientists in the world synthesized a series of cis-restricted CA-4 analogs, where the double bond has been replaced by introduction of non-heterocyclic groups or heterocyclic groups like β-lactam and oxadiazole. This paper reviews the most important approaches in analogs of combretastatin synthesis and presents structure-reactivity relationships for these compounds.
Synthesis, structural and spectroscopic properties of asymmetric schiff bases derived from 2,3-diaminopyridine
- Agnieszka Pazik
- Beata Kamińska
- Anna Skwierawska
- Łukasz Ponikiewski
2016 Pełny tekst CHEMICAL PAPERS
Two Schiff base derivatives, 4-(2-amino-3-pyridyliminomethyl)phenol (I) and 3-(2-amino-3- pyridyliminomethyl)nitrobenzene (II ), were synthesised and characterised by spectroscopy. The structure of I was determined by single crystal X-ray diffraction studies. The asymmetric Schiff base derived from 2,3-diaminopyridine selectively recognise transition and heavy metal cations, and some anion. Ligands I and II form stable complexes with Cu2+, Zn2+, Pb2+, Al3+ whereas ligand I also binds F− ions. The stoichiometry for the host : cation is 1 : 1 and 2 : 1. The addition of F− ion in CH3CN to ligand I causes a colour change of the solution from colourless to yellow. The binding behaviour of ligand I towards several ions was investigated using density functional theory calculations.
Synthesis, structure and properties of novel poly(hydroxyurethane)s obtained by non-isocyanate route
- Marcin Włoch
2016
Non-isocyanate polyurethanes (NIPUs) can be synthesized by polyaddition of five-membered bis(cyclic carbonate)s and primary diamines. NIPUs are an alternative for the commonly used (in the form of foams, elastomers, coatings or fibers) in the industry polyurethanes obtained using toxic and moisture sensitive diisocyanates, polyols and low-molecular weight chain extenders. The main aim of this work was to synthesize non-isocyanate polyurethanes using petrochemical and bio-based substrates. At the beginning the model hydroxyurethanes were synthesized using glycerol carbonate and selected diamines without the catalyst and the chemical structure of obtained products was investigated using 1HNMR and 13C NMR. The model study was performed to determine the yield of reaction, ratio of primary to secondary hydroxyl group, which are formed during the reaction and to indicate the side-products. The cyclic carbonate intermediates were synthesized by the reaction of diglycidyl ether of bisphenol A-based epoxy resin (EPIDIAN 5), poly(ethylene glycol)s with different molecular weights (300, 600, 1000, 1500 and 2000 g mol-1) and glycerol carbonate or epoxidized soybean oil and glycerol carbonate. The chemical structure (by 1H NMR method) and average molecular weight (by GPC analysis) of selected semi-products was determined. In the next step synthesized intermediates were reacted with selected diamines (i.e. 1,2-ethanediamine, 1,4-butanediamine, 1,6-hexanediamine, triethylene-tetramine or amine derivative of dimerized fatty acids PRIAMINE 1071). The chemical structure (using FTIR method), morphology (by AFM method), selected mechanical properties (i.e. tensile properties and hardness), dynamic mechanical properties (by DMTA method), glass transition temperature (by DSC method) and thermal stability (by TGA method) were determined for the obtained non-isocyanate polyurethanes.
Synthesis, Structure and Properties of Poly(ester-Urethane-Urea)s Synthesized Using Biobased Diamine
- Marcin Włoch
- Janusz Datta
2016 Pełny tekst Journal of Renewable Materials
Modern polymer science and technology is focused on the development of partial or fully green polymers. This focus is related to green chemistry trends, which propose using natural and renewable resources as monomers in the synthesis of polymers. In this study, biobased diamine was used as a chain extender of ester-urethane prepolymer. Obtained poly(ester-urethane-urea) contains 16 wt% of biobased diamine. There is mention of an amine curing agent that is an amine derivative of dimerized fatty acids (obtained from vegetable oils). Application of two chain extenders, i.e., 1,4-butanediol and biobased diamine (applied separately or in mixture), with different molecular weights and chemical structures, resulted in obtaining materials with diversifi ed properties. The chemical structure (by FTIR method), mechanical properties (tensile properties, hardness and elasticity), and thermomechanical properties (by DMTA method) were determined for the synthesized poly(ester-urethane-urea)s.
Synthesis, structure and properties of poly(ether-urethane)s synthesized using a tri-functional oxypropylated glycerol as a polyol
- Janusz Datta
- Paulina Kasprzyk
- Marcin Włoch
2016 Pełny tekst JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY
The main aim of this work was to obtain poly(ether-urethane)s using tri-functional polyoxyalkylene polyol (Rokopol G1000), which introducing the chemical cross-links into the structure of polyurethanes. Poly(ether-urethane)s were prepared using two-step method, called prepolymer method, which involves in the first step the reaction of 4,4'-diphenylmethane diisocyanate (MDI) and tri-functional polypropylene glycol glycerol triether polyol. In the second step, prepolymer chains were extended by using: 1,6-hexanediol, 1,4-butanediol in the mixture with poly(ethylene glycol), and poly(ethylene glycol). The prepolymer chains extending was realized at three different molar ratios of NCO groups (presented in prepolymer) to OH groups (presented in chain extender) i.e. 0.95, 1.00 or 1.05. The influence of chain extender type on the chemical structure, selected mechanical properties and termo-mechanical properties of the obtained poly(ether-urethane)s was investigated. The results showed that applying different types of chain extenders results in obtaining materials with diversified mechanical properties, but very similar thermal stability. The performance of obtained poly(ether-urethane)s is mostly affected by the chemical cross-links, which were introduced into soft segments by trifunctional polyetherol.
Synthetic lipopeptides as potential topical therapeutics in wound and skin care: in vitro studies of permeation and skin cells behaviour
- Monika Kukowska
- Michał Pikuła
- Magdalena Kukowska-Kaszuba
- Adriana Schumacher
- Krystyna Dzierzbicka
- Piotr Trzonkowski
2016 RSC Advances
Several Gly-His-Lys analogues were obtained to investigate their antimicrobial properties. Three lipophilic analogues with the structure numbering 1b, 2b, 4b, exhibit significant effect against bacteria and were selected for in vitro evaluation of skin cells behaviour. In the present studies, an in vitro model of wound repair, proliferative cell staining, and tracking of living cells were used. Cell proliferation and cell migration, as important actions during the wound repair process, were studied. All the analogues provided an optimal environment for the growth, development and viability of skin cells. Microscopic changes in the morphology of fibroblasts and keratinocytes confirmed the positive effect of all the analogues on their growth and condition. Franz-type diffusion studies and the behaviour of analogues in the in vitro model of permeation were also performed. Permeability and diffusion coefficients were measured using UV-Vis spectrophotometry and RP-HPLC techniques. A substantial increase of permeability parameters for the lipophilic analogues was noticed. The outcomes of these studies suggest that lipophilic analogues possess a high potential as topical therapeutics. In relation with their proved antimicrobial activity, their safety profile and great tolerance for human skin show that they may be applied in both skin care and wound therapies.
System do kondensacji wydychanego powietrza przy wykrywaniu biomarkerów chorób układu oddechowego
- Tomasz Chludziński
2016
Praca opisuje konstrukcję oraz testy urządzenia zbierającego skropliny wydychanego powietrza, w których znadują się biomarkery chorób układu oddechowego. Celem urządzenia jest zwiększenie koncentracji biomarkerów, które mogą być następnie wykrywane za pomocą przygotowanego spektrofotometru i pH-metru. W pracy przedstawiono szczegółowo konstrukcję oraz sposób analizy zbieranych próbek. Skuteczność działania urządzenia przetestowano na grupie ochotników oraz, w przeciągu wybranego okresu, na pojedynczej osobie. Uzyskane wyniki wskazują, że zaproponowane rozwiązania konstrukcyjne pozwalają koncentrować wybrane biomarkery (np. stężenie tlenków NOx, wartość pH) do poziomu pozwalającego na skuteczną detekcję.
System do kondensacji wydychanego powietrza przy wykrywaniu biomarkerów chorób układu oddechowego
- Tomasz Chludziński
2016 Elektronika : konstrukcje, technologie, zastosowania
Praca opisuje konstrukcję oraz testy urządzenia zbierającego skropliny wydychanego powietrza, w których znadują się biomarkery chorób układu oddechowego. Celem urządzenia jest zwiększenie koncentracji biomarkerów, które mogą być następnie wykrywane za pomocą przygotowanego spektrofotometru i pH-metru. W pracy przedstawiono szczegółowo konstrukcję oraz sposób analizy zbieranych próbek. Skuteczność działania urządzenia przetestowano na grupie ochotników oraz, w przeciągu wybranego okresu, na pojedynczej osobie. Uzyskane wyniki wskazują, że zaproponowane rozwiązania konstrukcyjne pozwalają koncentrować wybrane biomarkery (np. stężenie tlenków NOx, wartość pH) do poziomu pozwalającego na skuteczną detekcję.