Synthesis and cytotoxicity of fluorinated amino saccharides.

0551678 - ÚCHP 2022 CZ eng A - Abstrakt
Hamala, Vojtěch - Karban, Jindřich - Balouch, M. - Hrstka, R.
Synthesis and cytotoxicity of fluorinated amino saccharides.
Book of abstracts. 2021.
[Conference Advances in Organic, Bioorganic and Pharmaceutical Chemistry "LIBLICE 2021" /55./. 03.11.2021-06.11.2021, Špindlerův Mlýn]
Grant CEP: GA MŠMT(CZ) LTC20052
Institucionální podpora: RVO:67985858
Klíčová slova: fluorinated carbohydrates * cytotoxic aminnosaccharides * antitumor properties
Obor OECD: Organic chemistry

This work presents the synthesis and cytotoxicity of acetyl, propionyl, and butyryl esters of monofluorinated, difluorinated, and trifluorinated analogues of N-acetyl-D-glucosamine and N-acetyl-D-galactosamine. The cytotoxicity is expressed as IC50 values against the MDA-MB-231 cancer cell line (triple-negative breast cancer) and the HEK-293 non-cancerous cell line. It was confirmed that fluorination indeed enhances cytotoxicity especially for D-galactosamine analogues. In contrast to nonfluorinated analogues, no positive correlation between the ester alkyl chain length and cytotoxicity was observed as some acetyl esters and propionyl esters were more cytotoxic than butyryl esters. In vitro experiments indicate that recently discovered3 S-glyco-modification is an improbable cause of the observed cytotoxicity.
Trvalý link: http://hdl.handle.net/11104/0326914