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Introduction
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Publications
Publications (63)
Enantiomeric purity control is a must when working with chiral drugs. In this context, homochiral cycles consisting solely of 1 to 3 binaphthalene units interconnected with urea moieties were tested...
Homovanillate (HVA) and vanilmandelate (VMA) are recognized markers of diseases, including neuroblastoma. However, their detection in urine represents a challenging task due to the complexity of the matrix. Here, a design, synthesis and thorough investigation of polymerizable urea‐based receptors interacting with HVA and VMA are reported. The selec...
A urea‐based complexation site represents a building block customarily used in the design of receptors for anion recognition. Here we report a cyclization driven change of complexation preferences, leading to a urea‐based macrocyclic receptor with selectivity for heavier alkali metal cations. Moreover, the thorough 1H and 19F NMR, HRMS and X‐ray di...
Supramolecular structures, such as micelles, liposomes, polymerosomes or dendrimerosomes, are widely studied and used as drug delivery systems. The behavior of amphiphilic building blocks strongly depends on their spatial distribution and shape of polar and nonpolar component. This report is focused on the development of new versatile synthetic pro...
Three series of poly(ionic) carbosilane dendrimers peripherally functionalized with imidazolium groups substituted on N-3 with methyl, isopropyl and 2,6-diisopropylphenyl (Dipp) were prepared up to the 3rd generation together with model monovalent imidazolium iodides and used as N-heterocyclic carbene (NHC) precursors. Catalytic activity of model a...
A nitro group was used as an electrochemical binding/release switch in urea-based receptors for anions. The oxidized and reduced forms of the receptors were thoroughly studied, evaluating the impact of structural features on the binding affinity upon redox modification. In the case of a nitro group in the p- position to the urea moiety, the associa...
The repetition of urea-based binding units within the receptor structure does not only lead to monomer properties multiplication. As confirmed by spectroscopic studies, UV-Vis and 1H-NMR in classical or competitive titration mode, the attachment to a carrier allocates the active moieties to mutual positions predetermining the function of the whole...
Galectins are widely expressed galactose-binding lectins implied, for example, in immune regulation, metastatic spreading, and pathogen recognition. N-Acetyllactosamine (Galβ1-4GlcNAc, LacNAc) and its oligomeric or glycosylated forms are natural ligands of galectins. To probe substrate specificity and binding mode of galectins, we synthesized a com...
A novel approach to inducing anion transport over the dialytic membrane was proposed and successfully tested using the dihydrogen phosphate anion. The anion receptor based on isophthalamide was anchored on a dendritic skeleton, resulting in a macromolecular structure with a limited possibility to cross the dialytic membrane. The dendritic receptor...
Anions play an important role in biological systems. At the same time, many of them are the major environmental pollutants and substances endangering living organisms [1]. For these purposes the anion recognition, elimination and sensing would find application in many branches including application in medicine or environmental chemistry. Suitable e...
Multiple fluorination of glycostructures has emerged as an attractive way of modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis of a series of mono-, di- and trifluorinated N -acetyl-ᴅ-glucosamine and ᴅ-galactosamine analogs. The key intermediates are the corresponding multiply fluorinated glu...
Fully acetylated deoxyfluorinated hexosamine analogues and non-fluorinated 3,4,6-tri-O-acylated N-acetyl-hexosamine hemiacetals have previously been shown to display moderate anti-proliferative activity. We prepared a set of deoxyfluorinated GlcNAc and GalNAc hemiacetals that comprised both features: O-acylation at the non-anomeric positions with a...
The Tn antigen (GalNAcα1-Thr/Ser) is abundantly expressed in many tumors but rarely found in healthy tissues, which makes it an attractive epitope for antitumor immunotherapy. The use of the Tn antigen in the development of therapeutic antitumor vaccines is hampered by its low immunogenicity, which may be enhanced by deoxyfluorination of the GalNAc...
Three multiply positively charged β-cyclodextrin derivatives were prepared and ionically bound to a Nafion® 117 membrane. The derivatives differed only in the length of the linker, which connects the positively charged anchor to the cyclodextrin moiety. The resulting membranes exert preferential sorption of l-enantiomer of tryptophan from its racem...
Multiple fluorination of glycostructures has emerged as an attractive way of modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis of a series of mono-, di- and trifluorinated N -acetyl-D-glucosamine and D-galactosamine analogs. The key intermediates were the corresponding multiply fluorinated gl...
The introduction of chiral alkyl substituents into the lower rim of calix[4]arene immobilised in the 1,3-alternate conformation led to a system possessing a preorganised ureido cavity hemmed with chiral alkyl units in the near proximity. As shown by the ¹ H NMR titration experiments, these compounds can be used as receptors for chiral anions in DMS...
A composite membrane comprising a microfiber thermoplastic layer of a mixture of polyethylene and polypropylene and a nanofiber layer of a polymer selected from the group consisting of polyamides, polyurethanes, polyureas and mixtures thereof, which together form a laminate, and a polymer deposited on fibers and containing chiral monomer units deri...
The oxidative photocyclization of aromatic Schiff bases was investigated as a potential method for synthesis of phenanthridine derivatives, biologically active compounds with medical applications. Although it is possible to prepare the desired phenanthridines using such an approach, the reaction has to be performed in the presence of acid and TEMPO...
Insertion of carbon dioxide into structure of organic epoxides leads to a formation of valuable cyclic carbonates and polycarbonates. For the purpose of this process, we report here a series of recyclable organocatalysts with superior activity. Carbosilane dendrimers (1st to 3rd generation) are employed as a support to which periphery ammonium or p...
Fluorinated glycans are valuable probes for studying carbohydrate-protein interactions at the atomic level. Glucosamine is a ubiquitous component of glycans, and the stereoselective synthesis of α-linked fluorinated glucosamine is a challenge associated with the chemical synthesis of fluorinated glycans. We found that introducing a 6-O-acyl protect...
A sulphonamidic moiety was utilized as an electron‐withdrawing group for enhancement of anion complexation features of urea‐based receptors. A series of receptors varying in acidity of sulphonamidic and urea N H groups was synthesized and thoroughly tested. The individual complexation properties reflect deprotonation/complexation equilibrium in a g...
A series of new highly fluorophilic ionic liquids ( f > 110) was synthetized from 3‑iodopropyltris(3,3,4,4,5,5,6,6,7,7,8,8,8‐tridecafluorooctyl)silane and N‐alkyl imidazoles, followed by anion exchange. N‐heterocyclic carbenes generated in situ from obtained imidazolium salts were employed to catalyze redox esterification ( umpolung ) of cinnamalde...
Solid by-products generated in the winemaking process, can comprise valuable bioactive substances such as resveratrol and viniferin, which can be used in whole range of sectors including medicine, pharmacy, cosmetic industry etc. The changes in content of those stilbenes in extracts obtained by maceration and Soxhlet extraction were monitored using...
This paper is a continuation of study focused on thermodynamic properties of isomeric and quasi-isomeric ionic liquids. In this work 5 novel ionic liquids were synthesized, namely 1-(2-(2-ethoxyethoxy)ethyl)-3-alkylimidazolium bis(trifluoromethylsulfonyl)imides, where the alkyl stands for different C5 substituents. These species were characterized...
A series of unique composite membranes formed from a nanoµ fibrous material with different amounts of a chiral selector was used for separation of chiral drugs. The membrane performances were demonstrated through sorption tests, wherein they were soaked in an aqueous solution of racemic D,L-tryptophan (a model chiral drug). The changes in conc...
Introduction The controlled host-guest interaction is an ongoing challenge in supramolecular chemistry. The past decade have documented a vast assortment of supramolecular host-guest systems which are responsive to various stimuli such as pH, light, temperature, and redox. In this row the redox stimulus is the most powerful one since redox-induced...
Nowadays, there is a strong need for replacement of racemates by enantiomerically pure drugs. Enantioseparation on polymer membranes seems to be one of the promising and economically feasible technologies for this purpose. As a material for membrane construction, linear polymer molecules bearing covalently bonded chiral selectors are very promising...
Ethyl (R)-4-chloro-3-hydroxybutyrate ((R)-CHBE) is a versatile fine chemistry intermediate. It is used as a precursor in the synthesis of several pharmacologically valuable products, including L-carnitine. It is usually produced by means of stereoselective biotechnology methods in enzymatic reactions. An alternative preparation strategy towards eth...
Purpose
Cathinone derivatives are new psychoactive substance(s) (NPSs) with amphetamine-like effects and currently represent a great problem for public health. For this reason it is necessary to develop new sensitive, selective fast and inexpensive methods for large-scale screening of NPSs. The purpose of this study was to evaluate the capabilities...
The degradation of naphthalene in aqueous solutions containing submerged calcium peroxide-based and calcium hydroxide pellets was examined by using UV–vis and IR spectroscopy and mass spectrometry. The observed products are one-ring and fused rings quinoid and aromatic compounds containing OH and C(H)═O groups. Their formation is explained in ter...
Control of anomeric stereoselectivity in glycosylation with deoxofluorinated glycosyl donors is critical for assembly of fluorinated oligosaccharides. Here, we report the synthesis of benzylated 3-fluoro and 4-fluoro analogues of phenyl 1-thioglucosazide and galactosazide donors and evaluation of their stereoselectivity in glycosylation of a series...
Five optically active urea derivatives (1‐5) were used as NMR solvating agents for analysis of the optical purity of different 2‐arylpropanoic acids commonly used as nonsteroidal anti‐inflammatory drugs. These novel chiral solvating agents were more efficient at discriminating the respective enantiomers of targets than the chiral solvating agents k...
Glycodendrimers (Glyco-DDMs) represent a rapidly growing class of nanoparticles with promising properties for biomedical applications but concerns regarding the impact on human health and environment are still justified. Here we report, for the first time, the comparative study of in vivo developmental toxicity of carbosilane Glyco-DDMs and their c...
Macromolecular polyelectrolytes are gaining considerable attention for the application in medicine which implies their detailed characterization. We have successfully applied electrospray ionization mass spectrometry (ESI MS) to the analysis of defects in the structure of three generations of polycationic carbosilane dendrimers bearing series of qu...
A detailed study of diastereomeric complexes of chiral ureido‐1,1′‐binaphthalene derivatives with chiral 1‐phenylethanol showed that a derivative bearing only one urea unit makes five times more stable complex with (S)‐enantiomer than with (R)‐enantiomer of the alcohol. This phenomenon could be used in chiral discrimination processes. The influence...
Silica–titania mixed oxides and composites have been extensively studied, whereas the titanium monoxide (TiO)–silicon monoxide (SiO) counterparts still remain to be explored. Here, we report on structural changes in heated SiO–TiO mixtures. The changes in composition in intimately mixed μm-sized particles of TiO and SiO heated at 1000 °C were exami...
Silica–titania mixed oxides and composites have been broadly examined for their physical and catalytic properties, but titanium monoxide–silicon monoxide counterparts have yet drawn very little attention. Here we report that laser-induced processing of mixed silicon and titanium monoxides results in reactions yielding a nanostructured Ti/Si/O compo...
A family of ferrocene derivatives of the general formula [Fe(η⁵-C5H4CH2(p-C6H4)CH2(N-het))2] bearing saturated six- and five-membered N-heterocycles (N-het) was prepared. Reactions of the selected complexes with acids (HCl, acetic acid) afforded either the corresponding hydrochlorides or led to deprotection of the functionalized pendant N-heterocyc...
We report the synthesis and cytotoxicity evaluation of a completely new class of cationic carbosilane dendrimers functionalized with several different phosphonium peripheral groups and an ammonium functionalised one as a reference. The carbosilane dendrimers with NMe3, PMe3, P(Et2)2(CH2)3OH, PBu3, P(C6H4-OMe)3 and P(Ph)3 peripheral substituents wer...
A novel type of anion receptor, based on the intramolecularly bridged calix[4]arene immobilized in the cone conformation, is described. The reductive coupling of a distal dialdoxime using Zn/TiCl4 led to calix[4]arene with a meso-1,2-diaminoethane-1,2-diyl bridge that was transformed into the corresponding receptors by reaction with aryl isocyanate...
Infrared laser-induced ablation of an equimolar titanium monoxide–silicon monoxide mixture allows deposition of a continuous TiO-doped Si/SiOx/SiO2 film which undergoes collapse into micron-sized cylindrical-shaped plates. The film and the scrolls were analyzed by Raman and FTIR spectroscopy and electron microscopy and confirmed to be amorphous and...
The introduction of nosyl moieties onto the lower rim of the calix[4]arene skeleton led to the formation of compounds immobilised in cone conformations. Subsequent reduction of the nitro group and reaction with aryl isocyanates enabled the construction of new calixarene-based ligands for anion recognition. As proven by NMR and UV/vis titration expe...
Background:
Derivatives of D-glucosamine and D-galactosamine represent an important family of the cell surface glycan components and their fluorinated analogs found use as metabolic inhibitors of complex glycan biosynthesis, or as probes for the study of protein-carbohydrate interactions. This work is focused on the synthesis of acetylated 3-deoxy...
A set of tri- and diorganotin(iv) azides bearing 2-(N,N-dimethylaminomethyl)phenyl as a C,N-chelating ligand (LCN) has been prepared and structurally characterized. Triorganotin(iv) azides of the type LCNR2SnN3 (R = n-Bu (1) and Ph (2)) and (LCN)2(n-Bu)SnN3 are monomeric both in solution and in the solid state. The central tin atom in these species...
Attempts at Pd-catalyzed bridging in sulfoxide-bearing calixarenes containing various substituents (phenyl, ethyl, pyrimidin-2-yl) gave the expected compound only in the case of the ethyl derivative. However, the reaction of sulfoxides with BuLi revealed the ability of the pyrimidin-2-yl group to function unexpectedly as a leaving group. This enabl...
Grape cane, leaves and grape marc are waste products from viticulture, which can be used to obtain secondary stilbene derivatives with high antioxidant value. The presented work compares several extraction methods: maceration at laboratory temperature, extraction at elevated temperature, fluidized-bed extraction, Soxhlet extraction, microwave-assis...
While all the alkylation methods commonly used in the chemistry of classical calixarenes failed, tetranitrothiacalix[4]arene was easily alkylated using various alcohols under Mitsunobu reaction conditions. The products thus obtained were immobilized in the 1,3-alternate conformation as suggested by 1H NMR and proven unequivocally by X-ray analysis....
A novel calixarene derivative with dipyrromethane moieties on the lower rim was prepared. NMR spectroscopy revealed a high selectivity towards sodium cations and the ability to bind ion pairs.
A novel method enabling the synthesis of receptors based on the calix[4]arenes immobilized in the partial cone conformation is reported. The application of a protection/deprotection strategy using nosyl groups enables the regioselective introduction of functional groups (NO2 and NH2) into the upper rim of calix[4]arenes, leading finally to the subs...
The electrophilic substitution of 25,27-dipropoxy-26,28-dinosyloxycalix[4]arene leads exclusively to the para-substitution of the alkylated phenol rings, while in the next step, the protecting nosyl group can be easily removed using a basic hydrolysis. The overall process yields dialkoxycalix[4]arenes with the substitution on the alkylated rings—th...
Although originally designed for anion recognition, bis(N′-p-nitrophenylureido)calix[4]arenes immobilised in the 1,3-alternate conformation can act as receptors for small neutral molecules, such as sulfoxides and ketones. Their binding ability was studied both in solution and in the solid state using the combination of UV/vis, NMR, and X-ray crysta...
The new “heavy fluorous” cyclopentadienes C5H6−n[M(C2H4C6F13)3]n (M=Si, n=1 (3); n=2 (4) and M=Sn, n=1 (10)) were synthesized by reaction of cyclopentadienyl lithium with BrSi(C2H4C6F13)3 (2) or commercial BrSn(C2H4C6F13)3. Fluorous cyclopentadienes prepared in this manner contain three or six C6F13 groups, which significantly increase their solubi...
Treatment of the monospirodienone derivative of thiacalix[4]arene with various acidic agents (HCl and HBr) results in rearrangement of the thiacalixarene skeleton leading to the formation of a phenoxanthiin derivative in high yields (up to 80%). The structure of the unexpected product is confirmed using 1H and 13C NMR spectroscopy, and X-ray crysta...
A series of diureido-calix[4]arenes immobilised in the 1,3-alternate conformation was synthesised and systematically studied for their complexation ability. As revealed by 1H NMR and UV/vistitrations, this structural motif leads to very efficient ligands for anion recognition with high binding constants in nonpolar solvents. The comparison with the...
Mono, di-, tri- and tetraureido-calix[4]arenes in the cone, partial cone and 1,3-alternate conformations have been synthesised and their complexation ability towards selected anions has been studied. The structure-anion complexation ability relationship has been systematically monitored. A new type of very efficient ligands based on diureido-calix[...
The lines in (29)Si NMR spectra of silylated polyphenols and some other compounds are difficult to assign owing to the absence of couplings with protons outside the silyl group. The assignment can be derived through small (n)J((29)Si, (13)C) couplings (n > 1). Using a previously described method for measurements of these couplings, the assignment p...
Calix[4]arenes bearing two p-nitrophenyl-ureido functions at the upper rim are effective anion binders. The stoichiometry of complexation depends on the substitution pattern (distal vs proximal) and anion concentration. While the distally substituted receptor forms 1:1 complexes with anions, the corresponding proximal derivative prefers the 2:1 sto...
