Baraniak Dagmara, Ruszkowski Piotr, Baranowski Daniel, Framski Grzegorz, Boryski Jerzy
Institute of Bioorganic Chemistry, Polish Academy of Sciences , Poznań , Poland.
Department of Pharmacology, Faculty of Pharmacy, Poznań University of Medical Sciences , Poznań , Poland.
Nucleosides Nucleotides Nucleic Acids. 2019;38(12):980-1005. doi: 10.1080/15257770.2019.1641206. Epub 2019 Aug 5.
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'-- and 5'--propargyl-nucleosides as the alkyne components. Based on analysis of the , and 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 cytotoxicity in three human cancer cell lines: cervical (HeLa), oral (KB) and breast (MCF-7).
合成了两个系列具有非天然1,2,3-三唑连接的新型氟化核苷二聚体。所得到的分子是使用基于铜（I）催化的惠斯根叠氮化物-炔烃环加成反应的“点击”化学方法制备的。该反应在作为叠氮化物组分的3'-和5'-叠氮核苷与作为炔烃组分的3'-和5'-炔丙基核苷之间进行。基于对……的分析，我们估计了糖部分的构象偏好以及糖苷键周围的取向。所有所述的核苷二聚体类似物均通过光谱方法进行了表征，并在三种人类癌细胞系：宫颈癌细胞（HeLa）、口腔癌细胞（KB）和乳腺癌细胞（MCF-7）中评估了它们的细胞毒性。
