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Wyniki wyszukiwania dla: STEROID SULFATASE
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Synthesis and biological evaluation of fluorinated 3-phenylcoumarin-7-O-sulfamate derivatives as steroid sulfatase inhibitors
PublikacjaIn 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...
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Phosphate and Thiophosphate Biphenyl Analogs as Steroid Sulfatase Inhibitors
PublikacjaIn the present work, we report convenient methods for the synthesis and biological evaluation of phosphate and thiophosphate biphenyl derivatives exhibiting steroid sulfatase (STS) activity. The described synthesis is based on straightforward preparation of biphenyl-4-ol and 40-hydroxybiphenyl- 4-carboxylic acid ethyl ester modified with various phosphate or thiophosphate moieties. The inhibitory effects of these compounds were...
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Synthesis of bicoumarin thiophosphate derivatives as steroid sulfatase inhibitors
PublikacjaBased on the frameworks of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy- 7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c] chromen-6-one, a series of bicoumarin thiophosphate analogs have been synthesized and biologically evaluated. Additionally, their binding modes have been modeled using docking techniques. The inhibitory properties of the synthesized compounds...
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Steroid Sulfatase Inhibitors Based on Phosphate and Thiophosphate Flavone Analogs
PublikacjaA series of phosphate and thiophosphate flavone derivatives were synthesized and biologically evaluated in vitro for inhibition of steroid sulfatase (STS) activity. The described synthesis includes the straightforward preparation of 7-hydroxy-2-phenyl-4H-chromen-4-one 3a, 2-(4-fluorophenyl)-7-hydroxy-4H-chromen-4-one 3b, 7-hydroxy-2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one 3c, 7-hydroxy-2-(p-tolyl)-4H-chromen-4-one 3d modified...
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Synthesis and biological evaluation of fluorinated N-benzoyl and N-phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7-O-sulfamate as steroid sulfatase inhibitors
PublikacjaIn the present work, we report convenient methods for the synthesis of 3-(4-aminophenyl)-coumarin-7-O-sulfamate derivatives N-acylated with fluorinated analogues of benzoic or phenylacetic acid as steroid sulfatase (STS) inhibitors. The design of these potential STS inhibitors was supported by molecular modeling techniques. Additionally, computational docking methods were used to determine the binding modes of the synthesized inhibitors...
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Synthesis and steroid sulfatase inhibitory activities of N-alkanoyl tyramine phosphates and thiophosphates
PublikacjaA series of phosphate and thiophosphate analogs based on the frameworks of N-alkanoyl tyramines have been synthesized and biologically evaluated. Their binding modes have been modeled using docking techniques. The inhibitory effects of the synthesized compounds were tested on STS isolated from the human placenta as well as the MCF-7, MDA-MB-231 and SkBr3 cancer cell lines. Most of the new STS inhibitors possessed potent activity...
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Synthesis and biological evaluation of thiophosphate tricyclic coumarin derivatives as steroid sulfatase inhibitors
PublikacjaSteroid sulfatase (STS) enzyme inhibition is an important approach to the management of hormone-dependent breast cancer. In this paper, we report convenient methods for the synthesis and biological evaluation of thiophosphate tricyclic coumarin analogs exhibiting STS activity. The described methods are based on the straightforward preparation of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-2-one, 3-hydroxy- 7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one,...
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Geometry optimization of steroid sulfatase inhibitors - the influence on the free binding energy with STS
PublikacjaIn the paper we review the application of two techniques (molecular mechanics and quantum mechanics) to study the influence of geometry optimization of the steroid sulfatase inhibitors on the values of descriptors coded their chemical structure and their free binding energy with the STS protein. We selected 22 STS-inhibitors and compared their structures optimized with MM+, PM7 and DFT B3LYP/6–31++G* approaches considering separately...
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Phosphate tricyclic coumarin analogs as steroid sulfatase inhibitors: synthesis and biological activity.
PublikacjaIn the present work, we report convenient methods for the synthesis and biological evaluation of phosphate tricyclic coumarin derivatives as potential steroid sulfatase inhibitors. The described synthesis includes the straightforward preparation of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-6-one modified...
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Synthesis and steroid sulfatase inhibitory activities of N-phosphorylated 3-(4-aminophenyl)-coumarin-7-O-sulfamates
PublikacjaIn 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...
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Synthesis and biological evaluation of N-acylated tyramine sulfamates containing C-F bonds as steroid sulfatase inhibitors
PublikacjaSteroid sulfatase (STS) is responsible for the hydrolysis of biologically inactive sulfated steroids into their active un-sulfated forms and promotes the growth of various hormone-dependent cancers (e.g., breast cancer). Therefore, the STS enzyme is a promising therapeutic target for the treatment of steroid-sensitive cancers. Herein, we report the synthesis and biological evaluation of sulfamate analogs as potential STS inhibitors...
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Novel steroid sulfatase inhibitors based on N ‐thiophosphorylated 3‐(4‐aminophenyl)‐coumarin‐7‐O‐sulfamates
PublikacjaIn the present work, we described convenient methods for the synthesis ofN-thiophosphorylated 3-(4-aminophenyl)-coumarin-7-O-sulfamates as steroid sulfatase(STS) inhibitors. To design the structures of the potential STS inhibitors, molecularmodeling techniques were used. A computational docking method was used to deter-mine the binding modes of the synthesized inhibitors as well as to identify potentialinteractions between specified...
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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
PublikacjaThe 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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STEROIDS
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Development of Sulfamoylated 4‑(1-Phenyl‑1H‑1,2,3-triazol-4-yl)phenol Derivatives as Potent Steroid Sulfatase Inhibitors for Efficient Treatment of Breast Cancer
PublikacjaWe present here the advances achieved in the development of new sulfamoylated 4-(1-phenyl-1H-1,2,3-triazol-4-yl)phenol derivatives as potent steroid sulfatase (STS) inhibitors for the treatment of breast cancer. Prompted by promising biological results and in silico analysis, the initial series of similar compounds were extended, appending a variety of m-substituents at the outer phenyl ring. The inhibition profiles of the newly...
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New potent steroid sulphatase inhibitors based on 6-(1-phenyl-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives
PublikacjaIn the present work, we report a new class of potent steroid sulphatase (STS) inhibitors based on 6-(1-phenyl-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives. Within the set of new STS inhibitors, 6-(1-(1,2,3-trifluorophenyl)-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate 3L demonstrated the highest activity in the enzymatic assay inhibiting the STS activity to 7.98% at 0.5 µM concentration. Furthermore, to verify...
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Evidence for sex steroid receptors in feline brainstem
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SOCS3 is epigenetically up-regulated in steroid resistant nephrotic children.
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Chemometric Evaluation of Urinary Steroid Hormone Levels as Potential Biomarkers of Neuroendocrine Tumors
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SOCS3 and SOCS5 mRNA expressions may predict initial steroid response in nephrotic syndrome children
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Comparison of High Performance Liquid Chromatography Methods with Different Detectors for Determination of Steroid Hormones in Aqueous Matrices
PublikacjaThis paper presents the development and comparison of procedures for the qualitative and quantitative determination of five estrogenic compounds (17-a-ethynylestradiol, estrone, estradiol, estriol, and progesterone) in drinking water and wastewater samples. Five extraction columns and two disks were tested for their efficiency. The C18 columns were superior on the basis of cost for solid phase extraction of drinking water or sewage....
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Expression Profile of Genes Regulating Steroid Biosynthesis and Metabolism in Human Ovarian Granulosa Cells—A Primary Culture Approach
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Study of the chromatographic behavior of selected steroid hormones on aluminum oxide plates based on quantitative structure-retention relationships
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Comparative molecular modelling of biologically active sterols
PublikacjaMembrane sterols are targets for a clinically important antifungal agent – amphotericin B. The relatively specific antifungal action of the drug is based on a stronger interaction of amphotericin B with fungal ergosterol than with mammalian cholesterol. Conformational space occupied by six sterols has been defined using the molecular dynamics method to establish if the conformational features correspond to the preferential interaction...
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Relationships between biomarkers of inflammation, ovarian steroids, and age at menarche in a rural polish sample
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10-Methyl- and 9,10-dimethyl acridinium methyl sulfate
PublikacjaThe title compounds, C(14)H(12)N(+).CH(3)O(4)S(-), (I), and C(15)H(14)N(+).CH(3)O(4)S(-), (II), respectively, crystallize with the planar 10-methylacridinium or 9,10-dimethylacridinium cations arranged in layers, parallel to the twofold axis in (I) and perpendicular to the 2(1) axis in (II). Adjacent cations in both compounds are packed in a 'head-to-tail' manner. The methyl sulfate anion only exhibits planar symmetry in (II)....
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Steroid profiles as potential biomarkers in patients with urogenital tract cancer for diagnostic investigations analyzed by liquid chromatography coupled to mass spectrometry
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Molecular modelling of membrane sterols with the use of the GROMOS 96 forcefield
PublikacjaPodstawowym zadaniem tego projektu było udowodnienie zasadności stosowania pola siłowego GROMOS 96 do symulacji steroli błonowych metodą dynamiki molekularnej. Uzyskane wyniki jasno wskazują, że to pole siłowe bardzo dobrze nadaje się do symulacji silnie lipofilowych układów.
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Hyaluronan-Chondroitin Sulfate Anomalous Crosslinking Due to Temperature Changes
PublikacjaGlycosaminoglycans are a wide class of biopolymers showing great lubricating properties due to their structure and high affinity to water. Two of them, hyaluronic acid and chondroitin sulfate, play an important role in articular cartilage lubrication. In this work, we present results of the all-atom molecular dynamics simulations of both molecules placed in water-based solution. To mimic changes of the physiological conditions,...
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The Influence of Sulfate on Anaerobic Ammonium Oxidation in a Sequencing Batch Reactor
PublikacjaAnaerobic ammonia-oxidizing bacteria have a more comprehensive metabolism than expected - there may be other electron acceptors that oxidize ammonium nitrogen under anaerobic conditions, in addition to the well-known nitrite nitrogen, one of which is sulfate in the sulfammox process. Sulfate-containing compounds are part of the medium for the anammox process, but their concentrations are not particularly high (0.2 g MgSO4 ∙ 7H2O/dm3...
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Effect of alkyl sulfate on the phase behavior of microemulsions stabilized with monoacylglycerols
PublikacjaIn this study the effect of an anionic surfactant (sodium dodecyl sulfate SDS) and oils (hydrocarbons: C12-C16) on the formation and phase behavior of the systems of oil/monoacylglycerols (MAG):SDS/propylene glycol/water has been investigated. The effects of the surfactant mixture on the phase behavior and the concentrationof water or oil in the systems were studied at three temperatures (50, 55, 60 C). Electrical conductivity...
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Quantitative structure—retention relationships of some steroid and phenanthrene derivatives on cyano-, reversed-phase, and normal-phase thin-layer chromatography stationary phases
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Glioblastoma-derived spheroid cultures as an experimental model for analysis of EGFR anomalies
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Studies of the Interaction Dynamics in Albumin-Chondroitin Sulfate Systems by Recurrence Method
PublikacjaThe physicochemical basis of lubrication of articular cartilage is still not fully understood. However, the synergy between components of the synovial fluid can be a crucial factor that could explain this phenomenon. This work presents a nonlinear data analysis technique named the recurrence method, applied to the system involving two components of synovial fluid: albumin and chondroitin sulfate (CS) immersed in a water environment....
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Impact of Surfactant and Calcium Sulfate Type on Air-Entraining Effectiveness in Concrete
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Sulfate reducing ammonium oxidation (SULFAMMOX) process under anaerobic conditions
PublikacjaSulfate (SO42-) can be an electron acceptor for ammonium nitrogen (NH4+) oxidation under anaerobic conditions. The process is known as sulfammox and can be a viable alternative to conventional, nitrite (NO2-) dependent, anammox. Two bacterial species, including Bacillus Benzoevorans and Brocadia Anammoxoglobus Sulfate, can perform that process. With sulfammox, an economically inefficient pre-nitration step (due to aeration) is...
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Influence of sodium dodecyl sulfate presence on esterification of propylene glycol with lauric acid
PublikacjaZbadano wpływ obecności dodecylosiarczanu sodu na bezpośrednią estryfikację glikolu propylenowego kwasem laurynowym. Zbadano także rozkład wielkości cząstek mikroemulsji tworzącej się in situ w trakcie estryfikacji glikolu propylenowego kwasem laurynowym w obecności różnych stężeń dodecylosiarczanu. Oceniono wartość równowagi hydrofilowo - lipofilowej zsyntetyzowanych emulgatorów.
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Diamondized carbon nanoarchitectures as electrocatalytic material for sulfate-based oxidizing species electrogeneration
PublikacjaThe introduction of nanotechnology seems to be an imperative factor to intensify the synergic effects of electrocatalytic materials to produce strong oxidant species or to increase the active sites on their surfaces as well as to enhance the conversion yield in a fuel cell, high-added value products, electrolytic treatment for environmental protection or the detection limit in electroanalysis. Recently, a new type of 3D-diamond...
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Can sodium 1-alkylsulfonates participate in the sodium dodecyl sulfate micelle formation?
PublikacjaThe aggregation behavior of sodium dodecyl sulfate (SDS) was studied in an aqueous solution in the presence of increasing concentrations of selected sodium 1-alkylsulfonates, namely sodium 1-octanesulfonate, sodium 1-decanesulfonate, and sodium 1-dodecanesufonate. The critical micelle concentration (CMC) of SDS was determined by conductivity and fluorescence intensity measurements. The steady-state fluorescence quenching experiments...
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Optical activity of the guest azobenzene molecule generated by inclusion complexation with steroidal bile acids.
PublikacjaZsyntetyzowano krystaliczne kompleksy inkluzyjne azobenzenu z kwasami cholowym i deoksycholowym. Otrzymane związki inkluzyjne poddano badaniom przy wykorzystaniu spektroskopii dichroizmu kołowego w fazie stałej (KBr). Dodatni efekt Cottona, odpowiadający niskoenergetycznemu przejściu elektronowemu n-pi*, skorelowano z helikalnością M,M skręconej cząsteczki azobenzenu. Ponadto w celach porównawczych zmierzono dichroizm kołowy w...
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Fulminant hepatic failure in woman with iron and non-steroidal anti-inflammatory drug intoxication
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Non-steroidal anti-inflammatory drugs are safe with respect to the transcriptome of human dermal fibroblasts
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Statistical Method for Analysis of Interactions Between Chosen Protein and Chondroitin Sulfate in an Aqueous Environment
PublikacjaWe present the statistical method to study the interaction between a chosen protein and another molecule (e.g., both being components of lubricin found in synovial fluid) in a water environment. The research is performed on the example of univariate time series of chosen features of the dynamics of mucin, which interact with chondroitin sulfate (4 and 6) in four different saline solutions. Our statistical approach is based on recurrence...
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Thermodynamics, size, and dynamics of zwitterionic dodecylphosphocholine and anionic sodium dodecyl sulfate mixed micelles
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Mechanistic studies of the hydrolysis of p-nitrophenyl sulfate catalyzed by arylsulfatase from Helix pomatia
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Studies on water - polyethylene glycol - sulfates(VI) ternary systems used in conservation of wooden historical artefacts
PublikacjaW pracy omówiono wyniki badań cząstkowych objętości w układach dwu i trójskładnikowych: woda - PEG - siarczany oraz degradacji PEG w zbliżonych układach. Ma to ścisły związek z konserwacją drewna, gdzie podobne układy powstają w wyniku stosowania PEG do konserwacji drewna z zabytków podwodnych. W szczególności zaś siarczany powstają w kadłubie okrętu Vasa w wyniku utleniania nagromadzonej w nim siarki. Wykazano mi.in. zależność...
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The Effect of Sterols on Amphotericin B Self-Aggregation in a Lipid Bilayer as Revealed by Free Energy Simulations
PublikacjaAmphotericin B (AmB) is an effective but toxic antifungal drug, known to increase the permeability of the cell membrane, presumably by assembling into transmembrane pores in a sterol-dependent manner. The aggregation of AmB molecules in a phospholipid bilayer is, thus, crucial for the drug’s activity. To provide an insight into the molecular nature of this process, here, we report an atomistic molecular dynamics simulation study...
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Simultaneous determination of non-steroidal anti-inflammatory drugs and oestrogenic hormones in environmental solid samples
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From the pills to environment – Prediction and tracking of non-steroidal anti-inflammatory drug concentrations in wastewater
PublikacjaThe extend of environment pollution by pharmaceuticals is in a stage that required more automatic and integrated solutions. The non-steroidal anti-inflammatory drugs (NSAIDs) are one of the most popular pharmaceutical in the world and emerging pollutants of natural waters. The aim of the paper was to check the correlation of the sales data of selected NSAIDs (ibuprofen, naproxen, diclofenac) and their concentration in the WWTP...
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Microwave-Reactor-Based Preparation of Red Iron Oxide Pigment from Waste Iron Sulfate
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