Synthesis and Preliminary Anticancer Activity Assessment of N-Glycosides of 2-Amino-1,3,4-thiadiazoles
Katarzyna Żurawska,
Marcin Stokowy,
Patryk Kapica,
Monika Olesiejuk,
Agnieszka Kudelko,
Katarzyna Papaj,
Magdalena Skonieczna,
Wiesław Szeja,
Krzysztof Walczak,
Anna Kasprzycka
Affiliations
Katarzyna Żurawska
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego Street 4, 44-100 Gliwice, Poland
Marcin Stokowy
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego Street 4, 44-100 Gliwice, Poland
Patryk Kapica
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego Street 4, 44-100 Gliwice, Poland
Monika Olesiejuk
Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego Street 4, 44-100 Gliwice, Poland
Agnieszka Kudelko
Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego Street 4, 44-100 Gliwice, Poland
Katarzyna Papaj
Centre of Biotechnology, Silesian University of Technology, Krzywoustego Street 8, 44-100 Gliwice, Poland
Magdalena Skonieczna
Centre of Biotechnology, Silesian University of Technology, Krzywoustego Street 8, 44-100 Gliwice, Poland
Wiesław Szeja
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego Street 4, 44-100 Gliwice, Poland
Krzysztof Walczak
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego Street 4, 44-100 Gliwice, Poland
Anna Kasprzycka
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego Street 4, 44-100 Gliwice, Poland
The addition of 2-amino-1,3,4-thiadiazole derivatives with parallel iodination of differently protected glycals has been achieved using a double molar excess of molecular iodine under mild conditions. The corresponding thiadiazole derivatives of N-glycosides were obtained in good yields and anomeric selectivity. The usage of iodine as a catalyst makes this method easy, inexpensive, and successfully useable in reactions with sugars. Thiadiazole derivatives were tested in a panel of three tumor cell lines, MCF-7, HCT116, and HeLa. These compounds initiated biological response in investigated tumor models in a different rate. The MCF-7 is resistant to the tested compounds, and the cytometry assay indicated low increase in cell numbers in the sub- G1 phase. The most sensitive are HCT-116 and HeLa cells. The thiadiazole derivatives have a pro-apoptotic effect on HCT-116 cells. In the case of the HeLa cells, an increase in the number of cells in the sub-G1- phase and the induction of apoptosis was observed.
