Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.
Department of Genetics and Biotechnology, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.
Molecules. 2022 May 17;27(10):3191. doi: 10.3390/molecules27103191.
Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push-pull chromophores: 4,5-bis(arylethynyl)-1-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles' application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules.
通过铜催化的乙基 2-叠氮乙酸酯与碘代 1,3-二炔的 1,3-偶极环加成反应和随后的 Sonogashira 交叉偶联反应，合成了一系列新型基于三唑的推拉生色团：4,5-双（芳基乙炔基）-1-1,2,3-三唑。对它们光学性质的研究表明，所有分子都具有荧光性质，其斯托克斯位移值超过 150nm。三唑的荧光性质可以根据三唑核心的 C4 和 C5 原子上芳基乙炔基部分的芳环上连接的取代基的性质进行轻松调节。使用蛋白质和 HEK293 细胞系证明了 4,5-双（芳基乙炔基）-1,2,3-三唑用于标记的可能性。在两个不同的细胞系 HEK293 和 HeLa 上进行的 MTT 测试的结果表明，4,5-双（芳基乙炔基）三唑具有低细胞毒性，这使得它们成为标记和跟踪生物分子的有前途的荧光标记物。
