Synthesis and cytotoxicity of fluorinated amino saccharides

0565155 - ÚCHP 2023 FR eng A - Abstract
Hamala, Vojtěch - Červenková Šťastná, Lucie - Karban, Jindřich - Hrstka, R.
Synthesis and cytotoxicity of fluorinated amino saccharides.
Book of Abstracts. 2022. s. 58.
[Barrande-Vltava French-Czech Chemistry Meeting /11./. 28.08.2022-30.08.2022, Dijon]
R&D Projects: GA MŠMT(CZ) LTC20052
Institutional support: RVO:67985858
Keywords : carbohydrates * fluorinated carbohydrates * cytotoxic compounds * organometallic compounds
OECD category: Medicinal chemistry

In this project, we describe a structure-cytotoxicity study of new analogues of N acetyl-D-glucosamine and N-acetyl-D-galactosamine bearing three types of acyls (acetyl, propionyl and butyryl esters) and deoxyfluorinated at one, two or three different positions.2 The cytotoxicity against various types of cancer and non-cancerous cell lines is expressed as IC50 values. Fluorination indeed enhances cytotoxicity, however, in contrast to nonfluorinated
analogues, no positive correlation between the length of the ester alkyl chain and cytotoxicity was observed as some acetyl esters and propionyl esters were more cytotoxic than butyryl esters. In vitro experiments indicate that recently discovered2 S-glyco-modification is an improbable cause of the observed cytotoxicity.
Permanent Link: https://hdl.handle.net/11104/0336662