The Effect of Deoxyfluorination and O-Acylation on the Cytotoxicity of N-Acetyl-D-Gluco- and D-Galactosamine Hemiacetals.

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F21%3A00542205" target="_blank" >RIV/67985858:_____/21:00542205 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/21:43923073 RIV/60461373:22340/21:43923073 RIV/00209805:_____/21:00078632
Result on the web
<a href="http://hdl.handle.net/11104/0320364" target="_blank" >http://hdl.handle.net/11104/0320364</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/D1OB00497B" target="_blank" >10.1039/D1OB00497B</a>

Result language
angličtina
Original language name
The Effect of Deoxyfluorination and O-Acylation on the Cytotoxicity of N-Acetyl-D-Gluco- and D-Galactosamine Hemiacetals.
Original language description
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 an acetyl, propionyl and butanoyl group, and deoxyfluorination at selected positions. Determination of the in vitro cytotoxicity towards the MDA-MB-231 breast cancer and HEK-293 cell lines showed that deoxyfluorination enhanced cytotoxicity in most analogues. Increasing the ester alkyl chain length had a variable effect on the cytotoxicity of fluoro analogues, which contrasted with non-fluorinated hemiacetals where butanoyl derivatives had always higher cytotoxicity than acetates. Reaction with 2-phenylethanethiol indicated that the recently described S-glyco-modification is an unlikely cause of cytotoxicity.
Czech name
—
Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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