Ilona Wandzik
Silesian University of Technology
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Featured researches published by Ilona Wandzik.
Green Chemistry | 2014
Karol Erfurt; Ilona Wandzik; Krzysztof Walczak; Karolina Matuszek; Anna Chrobok
The synthesis and characterisation of new hydrogen-bond-rich ionic liquids and studies of their catalytic performance in Diels–Alder reactions are described. D-Glucose and chloroalcohols were used as the raw materials and as the sources of hydroxyl groups for the synthesis of ionic-liquid cations, whereas weakly coordinating bis(trifluoromethylsulfonyl)imide was used as the anion. The new ionic liquids were analysed by 1H and 13C NMR spectroscopy and by ESI-MS experiments, which confirmed their structures. In addition, the thermal data of the studied ionic liquids measured by differential scanning calorimetry and thermogravimetric analysis showed that these compounds tend to form a glass at temperatures in the range of −29 °C to −16 °C and are thermally stable from ambient temperature to at least 430 °C, most likely because of the presence of bis(trifluoromethylsulfonyl)imide anions. The performance of the ionic liquids in the model reaction of cyclopentadiene with diethyl maleate or methyl acrylate was investigated. The studied ionic liquids showed high activity even when present in catalytic amounts (4 mol% with respect to the dienophile). An increase in the number of hydroxyl groups present in the ionic liquid structure resulted in higher reaction rates.
Antiviral Research | 2010
Ewelina Krol; Ilona Wandzik; W. Szeja; Grzegorz Grynkiewicz; Boguslaw Szewczyk
Classical swine fever virus glycoproteins: E2, E(rns) (E0) and E1 are detected on the external part of viral particles and play a major role in the initial stages of viral infection. They form heterodimeric and homodimeric complexes needed to effectively infect host cells. Some glycosylation inhibitors, such as tunicamycin, which act at the early stages of glycan chain processing, can influence, not only glycosylation, but also the stability of E2 and E(rns) glycoproteins, effectively inhibiting the formation of glycoprotein complexes and virus yield. In our study we tested two of newly designed uridine derivatives of 2-deoxy sugars, IW3 and IW7 mimicking part of tunicamycin. We showed that inhibitors effectively arrest viral growth with IC(50) of 9 and 7microg/ml respectively, without significant toxicity for mammalian cells. Moreover, IW3 and IW7 reduced the formation of viral glycoproteins E2 and E(rns) in a dose-dependent manner. These compounds were further studied in order to elucidate the molecular mechanism of the antiviral effect using mammalian SK6 and insect Sf9 cell lines. We found that they inhibit N-glycosylation process of viral proteins at the late stage of glycan modification characteristic for mammalian cells. Due to the observed antiviral effect accompanied by low cytotoxicity, these inhibitors are potential candidates for anti-pestivirus therapy.
Journal of Liquid Chromatography & Related Technologies | 2012
Jadwiga Paszkowska; Beata Kania; Ilona Wandzik
The lipophilicity parameters R Mw of twenty-one uridine derivatives were determined by reverse phase thin layer chromatography (RP-TLC). Experiments were performed on RP-18 F254 plates with mixtures of methanol/water as the mobile phases. Amounts of methanol as an organic modifier were in the range 60–85% (v/v) in 5% increments. For nine compounds, logPexp values were determined by shake-flask method. A good correlation was found between logPexp and R Mw (r 0.96). Theoretical logP values for the studied compounds were calculated using nine different algorithms. A correlation matrix was formed to compare the experimental lipophilicity parameters: R Mw , logPexp and theoretical logP values. A good agreement between two experimental methods and theoretical logP values was achieved. The best agreement was obtained between AC/logP vs. logPexp, and R Mw (r 0.98 and 0.96, respectively).
Bioorganic Chemistry | 2009
Ilona Wandzik; Tadeusz Bieg; Marianna Czaplicka
A series of 2-deoxy-hexopyranosyl derivatives of uridine have been synthesized as analogues of UDP-sugar. These compounds were tested as inhibitors against bovine beta-1,4-galactosyltransferase I in fluorescent assays and showed no significant inhibition.
Nucleosides, Nucleotides & Nucleic Acids | 2008
Ilona Wandzik; Tadeusz Bieg; Monika Kadela
Synthesis of N 3,2′,3′-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5′-O-(2-deoxy-α-d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlmans catalyst without competing side reactions.
Tetrahedron Letters | 2000
G. Pastuch; Ilona Wandzik; W. Szeja
Abstract The title compound was synthesised and studied in several glycosylation procedures as an acceptor. Presented experiments indicate its value as a very stable, effective ‘latent’ glycosylating agent.
Journal of Carbohydrate Chemistry | 2012
Tadeusz Bieg; Katarzyna Kral; Jadwiga Paszkowska; W. Szeja; Ilona Wandzik
D-glucal, D-galactal, and their 6-O-TBDMS derivatives were benzylated in a two-step procedure under microwave conditions. In the first step glycals were converted into dibutylstannylene acetal or tributyltin ether intermediates, which were next alkylated with benzyl bromide in the presence of Bu4NBr. In all cases the 4-OH group stayed unsubstituted. Microwave-assisted benzylation contributes to a significant reduction of the reaction time in comparison with the classical synthesis, which requires several hours of heating. Supplemental materials are available for this article. Go to the publishers online edition of Journal of Carbohydrate Chemistry to view the free supplemental file.
Antiviral Research | 2013
Ewelina Krol; Ilona Wandzik; Beata Gromadzka; Dawid Nidzworski; Małgorzata Rychłowska; Marta Matlacz; Jolanta Tyborowska; Boguslaw Szewczyk
Influenza viruses are important pathogens that cause respiratory infections in humans and animals. Apart from vaccinations, antiviral drugs play a significant role in controlling spread of the disease. Influenza A virus contains two membrane glycoproteins on the external part of viral envelope: hemagglutinin (HA) and neuraminidase (NA), which are crucial for productive infection in target cells. In the present work, two derivatives of tunicamycin - uridine derivatives of 2-deoxy sugars (designated IW3 and IW7), which target the glycan processing steps during maturation of viral glycoproteins, were assayed for their ability to inhibit influenza A virus infection in vitro. Using the cytopathic effect (CPE) inhibition assay and viral plaque reduction assay we showed, that both IW3 and IW7 inhibitors exerted significant inhibitory effect on influenza A virus infection in MDCK cells without significant toxicity for the cells. Moreover, tested compounds selectively suppressed viral protein expression in a dose-dependent manner, suggesting that the mechanism of their antiviral activity may be similar to this shown previously for other viruses. We have also excluded the possibility that both inhibitors act at the replication step of virus life cycle. Using real-time PCR assay it was shown that IW3 and IW7 did not change the level of viral RNA in infected MDCK cells after a single round of infection. Therefore, inhibition of influenza A virus infection by uridine derivatives of 2-deoxy sugars, acting as glycosylation inhibitors, is a promising alternative approach for the development of new anti-influenza A therapy.
Synthetic Communications | 2003
W. Szeja; G. Pastuch; Ilona Wandzik; Nikodem Kuźnik; Grzegorz Grynkiewicz
Abstract Differential functionalization of the phenolic groups in Genistein by sequential silylation/acylation reactions, involving some unexpected regioselective O-silyl group replacement, is described.
International Journal of Molecular Sciences | 2017
Ewelina Krol; Ilona Wandzik; Martyna Krejmer-Rabalska; Boguslaw Szewczyk
Influenza virus infection is a major cause of morbidity and mortality worldwide. Due to the limited ability of currently available treatments, there is an urgent need for new anti-influenza drugs with broad spectrum protection. We have previously shown that two 2-deoxy sugar derivatives of uridine (designated IW3 and IW7) targeting the glycan processing steps during maturation of viral glycoproteins show good anti-influenza virus activity and may be a promising alternative approach for the development of new anti-influenza therapy. In this study, a number of IW3 and IW7 analogues with different structural modifications in 2-deoxy sugar or uridine parts were synthesized and evaluated for their ability to inhibit influenza A virus infection in vitro. Using the cytopathic effect (CPE) inhibition assay and viral plaque reduction assay in vitro, we showed that compounds 2, 3, and 4 exerted the most inhibitory effect on influenza virus A/ostrich/Denmark/725/96 (H5N2) infection in Madin-Darby canine kidney (MDCK) cells, with 50% inhibitory concentrations (IC50) for virus growth ranging from 82 to 100 (μM) without significant toxicity for the cells. The most active compound (2) showed activity of 82 μM with a selectivity index value of 5.27 against type A (H5N2) virus. Additionally, compound 2 reduced the formation of HA glycoprotein in a dose-dependent manner. Moreover, an analysis of physicochemical properties of studied compounds demonstrated a significant linear correlation between lipophilicity and antiviral activity. Therefore, inhibition of influenza A virus infection by conjugates of uridine and 2-deoxy sugars is a new promising approach for the development of new derivatives with anti-influenza activities.