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Formation of aqueous and alcoholic adducts of curcumin during its extraction
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Aberrant repair of etheno–DNA adducts in leukocytes and colon tissue of colon cancer patients
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Bulky DNA adducts in human sperm: relationship with fertility, semen quality, smoking, and environmental factors
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Electrochemical formation of the adduct between antitumor agent C_1311 and DNA nucleoside dG. 75.
PublicationPrzyjmuje się, że metaboliczna aktywacja przeciwnowotworowej pochodnej C_1311 jest procesem koniecznym dla jej aktywności przeciwnowotworowej. Wykazano wcześniej, że taka aktywacja prowadzi do kowalencyjnego wiązania się leku z DNA w komórce nowotworowej. Aby zbadać molekularny mechanizm powyższej reakcji metabolicznej przeprowadzono badania elektrochemicznego utleniania pochodnej C_1311. Wykazano w pracy, że dwa produkty elektrochemicznego...
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Metylacja DNA w rozwoju, diagnostyce i terapii nowotworów
PublicationDotychczas kowalencyjna modyfikacja DNA, jaką jest zarówno naturalna metylacja DNA, jak i addukty DNA egzogennych niskocząsteczkowych związków chemicznych, były ropatrywane z punktu widzenia genomu. W świetle obecnej wiedzy dotyczącej epigenomu można sądzić, że stosunkowo niewielkie modyfikacje czy to w postaci metylacji cytozyny, czy adduktu DNA mogą mieć znaczący wpływ na działanie komórki, a co za tym idzie także jej transformację...
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Synthesis and structural characterization of novel 2-benzimidazolylthioureas: adducts of natural isothiocyanatesand 2-amino-1-methylbenzimidazole
PublicationNa drodze syntezy chemicznej uzyskano addukty naturalnych izotiocyjanianów - alilu, benzylu i fenyloetylu i 2-amino-1-metylobenzoimidazolu. W następstwie optymalizacji warunków reakcji, poszczególne 2-benzimidazolilotiomoczniki otrzymano produkty z umiarkowanymi wydajnościami. Strukturę molekularną i krystaliczną produktów scharakteryzowano przy użyciu metod spektroskopowych i X-ray. Analiza uzyskanych widm pozwoliła stwierdzić,...
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Bypassing the stereoselectivity issue: transformations of Kinugasa adducts from chiral alkynes and non-chiral acyclic nitrones
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32P-postabeling detection of DNA adducts formed by 4-methyl-1-nitro-9-aminoacridine C-1748
PublicationWykazano zdolność do tworzenia przez nową pochodną 1-nitroakrydyny o symbolu C-1748, adduktów z DNA komórek nowotworowych oraz z DNA w systemie bezkomórkowym.
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DNA adduct formation by C-1748, a potent antitumor 4-methyl-1-nitroacridine of lowered toxicity.
Publication4-podstawione 1-nitroakrydyny reprezentują nową grupę pochodnych zsyntetyzowanych na Politechnice Gdańskiej. W porównaniu do macierzystych 1-nitroakrydyn związki te wykazują obniżoną toksyczność i podwyższoną aktywność przeciwnowotworową. Wiodąca pochodna 4-metylo-1-nitroakrydyna o symbolu C-1748 jest obecnie w przygotowaniu do I fazy badań klinicznych w leczeniu raka okrężnicy. Wprowadzenie elektrodonorowej grupy metylowej w...
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DNA modification by 1-nitroacridine derivatives. Comparison of 32P-Postlabeling and restriction enzyme analysis method for the detection of DNA adducts formed by 1-nitroacridines C-1748 and C-857
Publication4-podstawione 1-nitroakrydyny reprezentują nową grupę pochodnych akrydyny, zsyntetyzowanych na Politechnice Gdańskiej. Metoda 32P-postlabellingu wykazała, że pochodne C-1748 i C-857 tworzą od 4-6 adduktów DNA w systemie komórkowym i bezkomórkowym o innym rozkładzie plam chromatograficznych, jednakże niezależnym od zastosowanego systemu aktywacyjnego. Metoda enzymatycznej analizy restrykcyjnej pozwoliła natomiast śledzić kinetykę...
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Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA **1987 VOL.235 S. 1204-1208, 5 RYS. BIBLIOGR. 37 POZ.//
PublicationA DNA cross-link adduct of the antitumor agent mitomycin C (MC) to DNA has been isolated and characterized; the results provide direct proof for bifunctional alkylation of DNA by MC. Exposure of MC to Micrococcus luteus DNA under reductive conditions and subsequent nuclease digestion yielded adducts formed between MC and deoxyguanosine residues. In addition to the two known monoadducts, a bisadduct was obtained. Reductive MC activation...
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Phosphinophosphoranes: Mixed-Valent Phosphorus Compounds with Ambiphilic Properties
PublicationHerein, we present a simple synthesis of mixed-valent phosphinophosphoranes bearing three- and five-coordinate phosphorus centers. Compounds with phosphorus–phosphorus bonds were synthesized via a reaction of lithium phosphides RR′PLi with cat2PCl (cat = catecholate), whereas derivatives with methylene-linked phosphorus centers were obtained via a reaction of phosphanylmethanides RR′CH2Li with cat2PCl. The presence of accessible...
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DNA restriction analysis as a supportive tool in mechanistic studies carried out by 32P-postlabelling
PublicationNumerous antitumor and carcinogenic compounds are able to modify DNA by forming covalent bonds with its constituents, while some anticarcinogenic compounds are known to prevent such a modification. All these processes are of vital biological import_ance, though deeper inside into factors influencing formation of DNA adducts is difficult due to the low level of their occurrence. 32P-Postlabelling approach ensures very sensitive...
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Covalent DNA modification by products of myrosinase catalysed glucosinolate degradation in cell-free system
PublicationThe bioactive phytochemicals found in Brassica vegetables belonging to glucosinolates (GLS) and especially the products of their degradation isothiocyanates (ITC) and indoles are regarded as the most promising cancer chemopreventive compounds. These secondary metabolites constitute defence system repelling or preventing the development of agrophages attacking brassica plants. The antibiological properties of these compounds suggest...
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Tetrakis(m2-methanol-k2O:O)bis(methanol-kO)-(m2-tri-tert-butoxysilane-thiolato-k3S:O,S)-bis(tri-tert-butoxysilanethiolato-k2O,S)-tetrasodium(i)
PublicationZwiązek [Na4(C12H27O3SSi)4(CH4O)6] jest rozpatrywany jako addukt trzech jonów - dwujądrowego kationu [Na2(MeOH)6]2+ oraz dwóch anionów [Na{SSi(OtBu)3}2] - utworzony dzięki istnieniu krótkich kontaktów pomiędzy tymi jonami.Obecność mostków siarczkowych i tlenkowych oraz wiązań wodorowych O-H...O and O-H...S, sprawia, że w rezultacie wszystkie atomy Na w czterojądrowym kompleksie są pięciokoordynacyjne.
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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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Diphosphination of CO2 and CS2 mediated by frustrated Lewis pairs - catalytic route to phosphanyl derivatives of formic and dithioformic acid
PublicationThe first example of CO2 diphosphination is described. Reactions of unsymmetrical diphosphanes with CE2 (E = O, S) catalyzed by BPh3 insert a CE2 molecule into the P-P bond with formation of the products of the general formula R2P-E-C(=E)-PR2. The obtained CO2 adducts arise from synergistic interaction of diphosphane and borane with CO2 molecule.
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Phosphinoborinium cation: a synthon for cationic B-P bond systems
PublicationHerein, we report access to phosphinoborinium cations via heterolytic cleavage of the boron-bromide bond in bromophosphinoborane. The product of the reaction was isolated as a dimeric dication possessing a planar P2B2 core. Activation of C-H and C-P bonds in the dication led to formation of the borinium-phosphaborene adduct. Reactivity studies revealed that title cation exhibits ambiphilic properties and intramolecular frustrated...
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Oznaczanie neurotoksyny, β-N-metylamino-L-alaniny (BMAA), w materiale biologicznym
Publicationβ-N-metylamino-L-alaniny (BMAA) jest naturalnie występującym niebiałkowym aminokwasem. W strukturze związku występuje grupa karboksylowa o pKa1 2,1 , pierwszorzędowa grupa aminowa o pKa2 6,5 i drugorzędowa grupa aminowa o pKa3 9,8. Przy fizjologicznych wartościach pH (7,4), w obecności CO2/HCo3-, BMAA tworzy węglanowe addukty (BMAA-α - NCO2 i BMAA-β-NCO2) o działaniu agonistycznym względem receptorów glumatinianu. Efektem jest...
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The extended version of restriction analysis approach for the examination of the ability of low-molecular-weight compounds to modify DNA in a cell-free system
PublicationOne of the primary requirements in toxicology is the assessment of ability of chemicals to induce DNA covalent modification. There are several well-established methods used for this purpose such as 32P-Postlabeling or HPLC-MS. However, all of these approaches have difficult to overcome limitations, which prevents their use in genotoxin screening. Here, we describe the simple protocol exploiting specificity of restriction enzymes...
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The products of electro- and photochemical oxidation of 2-hydroxyacridinone, the reference compound of antitumor imidazoacridinone derivatives
PublicationBadano reakcje elektrochemicznego utleniania 2-hydroksyakrydonu, związku modelowego aktywnych przeciwnowotworowo pochodnych imidazoakrydonu. Do badań zastosowano metody woltamperometrii cyklicznej, metodę spektroelektrochemiczną oraz elektrolizę przy kontrolowanym potencjale. Badano też reakcje fotochemicznego utleniania. Badania prowadzono w ramach szerszego problemu poznania przemian aktywacji metabolicznej pochodnych hydroksyakrydonu...
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Understanding the kinetics and atmospheric degradation mechanism of chlorotrifluoroethylene (CF2=CFCl) initiated by OH radicals
PublicationThe atmospheric degradation of chlorotrifluoroethylene (CTFE) by OH˙ was investigated using density functional theory (DFT). The potential energy surfaces were also defined in terms of single-point energies derived from the linked cluster CCSD(T) theory. With an energy barrier of −2.62 to −0.99 kcal mol−1 using the M06-2x method, the negative temperature dependence was determined. The OH˙ attack on Cα and Cβ atoms (labeled pathways...
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Chromogenic macrocyclic derivatives of azoles - synthesis and 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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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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Topochemical, Single‐Crystal‐to‐Single‐Crystal [2+2] Photocycloadditions Driven by Chalcogen‐Bonding Interactions
PublicationThe 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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Preparation of DNA films for studies under vacuum conditions
PublicationExperiments were carried out to determine the optimum conditions required for the preparation of uniform films of supercoiled plasmid DNA to be used in irradiation experiments under high vacuum conditions. Investigations reveal that significant damage to the DNA molecules occurs due to the evacuation process when films were formed from DNA samples in ultra high purity water only. A variety of bases were tested for their possible...
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A strong preference for the TA/TA dinucleotide step discovered for an acridine-based, potent antitumor dsDNA intercalator, C-1305: NMR-driven structural and sequence-specificity studies
PublicationTriazoloacridinone C-1305, a potent antitumor agent recommended for Phase I clinical trials, exhibits high activity towards a wide range of experimental colon carcinomas, in many cases associated with complete tumor regression. C-1305 is a well-established dsDNA intercalator, yet no information on its mode of binding into DNA is available to date. Herein, we present the NMR-driven and MD-refined reconstruction of the 3D structures...
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Budowa chemiczna i setreostruktura kowalencyjnych adduktów wybranych przeciwnowotworowych pochodnych akrydyny z zasadami DNA
ProjectsProject realized in Faculty of Chemistry according to UMO-2018/28/T/ST5/00165 agreement from 2018-09-14
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Biomarkers of alcohol consumption in body fluids - possibilities and limitations of application in toxicological analysis
PublicationEthyl alcohol is the most popular legal drug, but its excessive consumption causes social problems. Despite many public campaigns against alcohol use, car accidents, instances of aggressive behaviour, sexual assaults and deterioration in labor productivity caused by inebriated people is still commonplace. Fast and easy diagnosis of alcohol consumption is required in order to introduce proper and effective therapy, and is crucial...
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DNA methylation in cancer development, diagnosis and therapy-multiple opportunities for genotoxic agents to act as methylome disruptors or remediators
PublicationThe role of DNA methylation and recently discovered hydroxymethylation in the function of the human epigenome is currently one of the hottest topics in the life sciences. Progress in this field of research has been further accelerated by the discovery that alterations in the methylome are not only associated with key functions of cells and organisms, such as development, differentiation and gene expression, but may underlie a number...
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Genotoxic properties of glucosinolates and isothiocyanates present in Brassica vegetables
PublicationThe bioactive phytochemicals found in Brassica vegetables, in this number glucosinolates (GLS), as well as products of their degradation such as isothiocyanates (ITC) and indoles, are regarded as the most promising chemopreventive compounds. These secondary metabolites display stron antibiological activity and constitute defence system preventing the development of agrophages attacking Brassica plants. Such properties suggest...
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An investigation on the chemistry of the R2P=P ligand: reactions of a phosphanylphosphinidene complex of tungsten(VI) with electrophilic reagents
PublicationThe nucleophilic properties of the title compound [(2,6-i-Pr2C6H3N)2(Cl)W(η2-t-Bu2PvP)]Li·3DME (1) were investigated in reactions with selected electrophilic reagents such as MeI, M(CO)5THF (M = Cr, Mo, W), AlCl3, and GaCl3. Methylation of 1 by MeI yields phosphanylphosphido complexes [(2,6-i-Pr2C6H3N)2W(X)(1,2-η-t-Bu2PvP–CH3)] (X = Cl, I) (2-Cl/2-I) with the formation of a new P–C bond. Moreover, 1 reacts with electrophilic compounds...
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Transparent nanocomposite coatings based on epoxy and layered double hydroxide: Nonisothermal cure kinetics and viscoelastic behavior assessments
PublicationLayered double hydroxide (LDH) has a particular place in clay family because of its flame retardant action. The nanoplatelet-like structure of LDH makes possible development of polymer composites with cationic or anionic nature structures in which macromolecules are positioned in between nanoplatelet galleries. In this work, neat epoxy and its transparent nanocomposite coatings with sodium dodecylbenzene sulfonate (SDBS)-modified...
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Monomeric Triphosphinoboranes: Intramolecular Lewis Acid–Base Interactions between Boron and Phosphorus Atoms
PublicationHerein, we present the synthesis of the first fully characterized monomeric triphosphinoboranes. The simple reaction of boron tribromide with three equivalents of bulky lithium phosphide tBu2PLi yielded triphosphinoborane (tBu2P)3B. Triphosphinoboranes with diversified phosphanyl substituents were obtained via a two-step reaction, in which isolable bromodiphosphinoborane (tBu2P)2BBr is first formed and then reacts with one equivalent...
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Problem of aggregation in dye-DNA interaction, calorimetry studies
PublicationNucleic acids are the biological target for many antimicrobial, antitumor and antiviral drugs. Ligand-DNA interactions can be classified into two major categories: 1. covalent binding, which can provide to intermolecular adducts, 2. physico-chemical interactions, which can be divided into intercalation (e.g. adriamycin) or groove binding (e.g. dystamycin). There are several methods to investigate interactions between drug and DNA....
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Chemiluminogenic acridinium salts: A comparison study. Detection of intermediate entities appearing upon light generation
PublicationThe nine derivatives of acridine-9-carboxylic acid (CMADs) capable for chemiluminescence (CL), representing various classes of compounds were isolated in a chemically pure state (assessed by RP-HPLC) and identified using high resolution mass spectrometry (ESI-QTOF) and magnetic resonance (1H NMR) techniques. Among them are aryl acridinium esters, containing certainly selected and located substituents in both aromatic systems, an...
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Electrochemical simulation of metabolic reduction and conjugation reactions of unsymmetrical bisacridine antitumor agents, C-2028 and C-2053
PublicationElectrochemistry (EC) coupled with analysis techniques such as liquid chromatography (LC) and mass spectrometry (MS) has been developed as a powerful tool for drug metabolism simulation. The application of EC in metabolic studies is particularly favourable due to the low matrix contribution compared to in vitro or in vivo biological models. In this paper, the EC(/LC)/MS system was applied to simulate phase I metabolism of the representative...
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Efficient Method for the Concentration Determination of Fmoc Groups Incorporated in the Core-Shell Materials by Fmoc–Glycine
PublicationIn this paper, we described the synthesis procedure of TiO2@SiO2 core-shell modified with 3-(aminopropyl)trimethoxysilane (APTMS). The chemical attachment of Fmoc–glycine (Fmoc–Gly–OH) at the surface of the core-shell structure was performed to determine the amount of active amino groups on the basis of the amount of Fmoc group calculation. We characterized nanostructures using various methods: transmission electron microscope...
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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
PublicationSingle-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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An insight into the mixed quantum mechanical-molecular dynamics simulation of a ZnII-Curcumin complex with a chosen DNA sequence that supports experimental DNA binding investigations
PublicationAn important aspect of research pertaining to Curcumin (HCur) is the need to arrest its degradation in aqueous solution and in biological milieu. This may be achieved through complex formation with metal ions. For this reason, a complex of HCur was prepared with ZnII, that is not likely to be active in redox pathways, minimizing further complications. The complex is monomeric, tetrahedral, with one HCur, an acetate and a molecule...
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Chemical investigation on the mechanism and kinetics of the atmospheric degradation reaction of Trichlorofluoroethene by OH⋅ and Its subsequent fate in the presence of O2/NOx
PublicationThe M06-2X/6-311++G(d,p) level of theory was used to examine the degradation of Trichlorofluoroethene (TCFE) initiated by OH⋅ radicals. Additionally, the coupled-cluster single-double with triple perturbative [CCSD(T)] method was employed to refine the single-point energies using the complete basis set extrapolation approach. The results indicated that OH-addition is the dominant pathway. OH⋅ adds to both the C1 and C2 carbons,...