Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics
Language English Country Netherlands Media print-electronic
Document type Journal Article
PubMed
32004953
DOI
10.1016/j.carres.2019.107905
PII: S0008-6215(19)30585-3
Knihovny.cz E-resources
- Keywords
- Alkyl glycoside, Antimicrobial activity, Cell cycle, Cytotoxicity, Glycolipid mimetic, SAXS,
- MeSH
- Anti-Bacterial Agents chemical synthesis chemistry pharmacology MeSH
- Cell Line MeSH
- A549 Cells MeSH
- K562 Cells MeSH
- X-Ray Diffraction MeSH
- Enterococcus faecalis drug effects MeSH
- Galactose chemical synthesis chemistry pharmacology MeSH
- Glycosides chemical synthesis chemistry pharmacology MeSH
- HCT116 Cells MeSH
- Humans MeSH
- Lipid Bilayers chemistry MeSH
- Scattering, Small Angle MeSH
- Microbial Sensitivity Tests MeSH
- Molecular Structure MeSH
- Cell Proliferation MeSH
- Antineoplastic Agents chemical synthesis chemistry pharmacology MeSH
- Carbohydrate Sequence MeSH
- Cell Survival drug effects MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Anti-Bacterial Agents MeSH
- Galactose MeSH
- Glycosides MeSH
- Lipid Bilayers MeSH
- Antineoplastic Agents 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.
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