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.

Department of Chemical Engineering University of Chemistry and Technology Technická 3 166 28 Prague 6 Prague Czech Republic

Institute of Chemical Process Fundamentals of the CAS v v i Rozvojová 135 16502 Praha 6 Czech Republic

Institute of Chemical Process Fundamentals of the CAS v v i Rozvojová 135 16502 Praha 6 Czech Republic and University of Chemistry and Technology Prague Technická 5 16628 Praha 6 Czech Republic

Research Centre for Applied Molecular Oncology Masaryk Memorial Cancer Institute žlutý kopec 7 Brno 65653 Czech Republic

References provided by Crossref.org