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Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics
P. Džubák, S. Gurská, K. Bogdanová, D. Uhríková, N. Kanjaková, S. Combet, T. Klunda, M. Kolář, M. Hajdúch, M. Poláková,
Jazyk angličtina Země Nizozemsko
Typ dokumentu časopisecké články
Grantová podpora
NV16-32302A
MZ0
CEP - Centrální evidence projektů
- MeSH
- antibakteriální látky chemická syntéza chemie farmakologie MeSH
- buněčné linie MeSH
- buňky A549 MeSH
- buňky K562 MeSH
- difrakce rentgenového záření MeSH
- Enterococcus faecalis účinky léků MeSH
- galaktosa chemická syntéza chemie farmakologie MeSH
- glykosidy chemická syntéza chemie farmakologie MeSH
- HCT116 buňky MeSH
- lidé MeSH
- lipidové dvojvrstvy chemie MeSH
- maloúhlový rozptyl MeSH
- mikrobiální testy citlivosti MeSH
- molekulární struktura MeSH
- proliferace buněk MeSH
- protinádorové látky chemická syntéza chemie farmakologie MeSH
- sacharidové sekvence MeSH
- viabilita buněk účinky léků MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
A series of 19 synthetic alkyl and thioalkyl glycosides derived from d-mannose, d-glucose and d-galactose and having C10-C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-d-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-d-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.
Citace poskytuje Crossref.org
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- $a Džubák, Petr $u Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University Olomouc, Hnevotinska 5, 779 00, Olomouc, Czech Republic.
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- $a Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics / $c P. Džubák, S. Gurská, K. Bogdanová, D. Uhríková, N. Kanjaková, S. Combet, T. Klunda, M. Kolář, M. Hajdúch, M. Poláková,
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- $a A series of 19 synthetic alkyl and thioalkyl glycosides derived from d-mannose, d-glucose and d-galactose and having C10-C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-d-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-d-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.
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- $a Bogdanová, Kateřina $u Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University Olomouc, Hnevotinska 5, 779 00, Olomouc, Czech Republic.
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- $a Uhríková, Daniela $u Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojarov 10, 832 32, Bratislava, Slovakia.
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- $a Kanjaková, Nina $u Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojarov 10, 832 32, Bratislava, Slovakia.
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- $a Combet, Sophie $u Laboratoire Léon Brillouin (CEA/CNRS), CEA Saclay, 91191, Gif-sur-Yvette Cedex, France.
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- $a Klunda, Tomáš $u Institute of Chemistry, Center for Glycomics, Slovak Academy of Sciences, Dubravska cesta 9, SK-845 38, Bratislava, Slovakia.
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- $a Kolář, Milan $u Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University Olomouc, Hnevotinska 5, 779 00, Olomouc, Czech Republic.
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- $a Hajdúch, Marian $u Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University Olomouc, Hnevotinska 5, 779 00, Olomouc, Czech Republic. Electronic address: marian.hajduch@upol.cz.
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- $a Poláková, Monika $u Institute of Chemistry, Center for Glycomics, Slovak Academy of Sciences, Dubravska cesta 9, SK-845 38, Bratislava, Slovakia. Electronic address: Monika.Polakova@savba.sk.
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