Issue 20, 2021

The effect of deoxyfluorination and O-acylation on the cytotoxicity of N-acetyl-d-gluco- and d-galactosamine hemiacetals

Abstract

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.

Graphical abstract: The effect of deoxyfluorination and O-acylation on the cytotoxicity of N-acetyl-d-gluco- and d-galactosamine hemiacetals

Supplementary files

Article information

Article type
Paper
Submitted
15 Mac 2021
Accepted
26 Apr 2021
First published
27 Apr 2021

Org. Biomol. Chem., 2021,19, 4497-4506

The effect of deoxyfluorination and O-acylation on the cytotoxicity of N-acetyl-D-gluco- and D-galactosamine hemiacetals

V. Hamala, L. Červenková Šťastná, M. Kurfiřt, P. Cuřínová, M. Balouch, R. Hrstka, P. Voňka and J. Karban, Org. Biomol. Chem., 2021, 19, 4497 DOI: 10.1039/D1OB00497B

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