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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/60461373:22310/21:43923073 RIV/60461373:22340/21:43923073 RIV/00209805:_____/21:00078632

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Organic & Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

1477-0539

Svazek periodika

19

Číslo periodika v rámci svazku

20

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

4497-4506

Kód UT WoS článku

000647139700001

EID výsledku v databázi Scopus

2-s2.0-85106563567