Nucleoside dimers analogs containing floxuridine and thymidine with unnatural linker groups: synthesis and cancer line studies. Part III

Nucleosides, Nucleotides & Nucleic Acids
Dagmara BaraniakJerzy Boryski

Abstract

Two series of novel fluorinated nucleosides dimers with an unnatural 1,2,3-triazole linkage were synthesized. The obtained molecules were prepared using "click" chemistry approach based on copper(I) catalyzed Huisgen azide-alkyne cycloaddition. It was performed between 3'- and 5'-azido-nucleosides as the azide components, and the 3'-O- and 5'-O-propargyl-nucleosides as the alkyne components. Based on analysis of the 3JHH, 3JH1'C2 and 3JH1'C6 we estimated conformational preferences of sugar part and orientation around glycosidic bond. All described nucleosides dimers analogs were characterized by spectroscopic methods and evaluated for their in vitro cytotoxicity in three human cancer cell lines: cervical (HeLa), oral (KB) and breast (MCF-7).

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Aug 1, 2014·ChemMedChem·Alberto MassarottiGian Cesare Tron
Nov 6, 2015·Quarterly Reviews of Biophysics·Afaf H El-Sagheer, Tom Brown
Feb 26, 2016·Nucleosides, Nucleotides & Nucleic Acids·Dagmara BaraniakJerzy Boryski
Dec 28, 2018·Nucleosides, Nucleotides & Nucleic Acids·Lucyna MichalskaDagmara Baraniak

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Citations

Nov 26, 2020·Current Protocols in Nucleic Acid Chemistry·Guillaume ClavéMichael Smietana
Feb 23, 2020·Organic Letters·Guillaume ClavéMichael Smietana
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alexis PaquinGervais Bérubé

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