4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications |
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| Authors: | Anastasia I. Govdi Polina V. Tokareva Andrey M. Rumyantsev Maxim S. Panov Johannes Stellmacher Ulrike Alexiev Natalia A. Danilkina Irina A. Balova |
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| Affiliation: | 1.Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia; (P.V.T.); (M.S.P.); (N.A.D.);2.Department of Genetics and Biotechnology, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia;3.Department of Physics, Institute of Experimental Physics, Freie Universität Berlin, Arnimalllee 14, 14195 Berlin, Germany; (J.S.); (U.A.) |
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| Abstract: | 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)-1H-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. |
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| Keywords: | 1,2,3-triazoles 1,3-diynes azide– alkyne cycloaddition Sonogashira cross-coupling fluorescence bioimaging cytotoxicity |
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