4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications
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<i>H</i>-1,2,3-triazoles. The study of their optical...
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MDPI AG
2022-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/10/3191 |
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| author | Anastasia I. Govdi Polina V. Tokareva Andrey M. Rumyantsev Maxim S. Panov Johannes Stellmacher Ulrike Alexiev Natalia A. Danilkina Irina A. Balova |
| author_facet | Anastasia I. Govdi Polina V. Tokareva Andrey M. Rumyantsev Maxim S. Panov Johannes Stellmacher Ulrike Alexiev Natalia A. Danilkina Irina A. Balova |
| author_sort | Anastasia I. Govdi |
| collection | DOAJ |
| description | 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<i>H</i>-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. |
| first_indexed | 2024-03-10T03:19:53Z |
| format | Article |
| id | doaj.art-2339ba8db8a54f16b09a5bc87564a0ce |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:19:53Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2339ba8db8a54f16b09a5bc87564a0ce2023-11-23T12:22:34ZengMDPI AGMolecules1420-30492022-05-012710319110.3390/molecules271031914,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and ApplicationsAnastasia I. Govdi0Polina V. Tokareva1Andrey M. Rumyantsev2Maxim S. Panov3Johannes Stellmacher4Ulrike Alexiev5Natalia A. Danilkina6Irina A. Balova7Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, RussiaInstitute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, RussiaDepartment of Genetics and Biotechnology, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, RussiaInstitute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, RussiaDepartment of Physics, Institute of Experimental Physics, Freie Universität Berlin, Arnimalllee 14, 14195 Berlin, GermanyDepartment of Physics, Institute of Experimental Physics, Freie Universität Berlin, Arnimalllee 14, 14195 Berlin, GermanyInstitute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, RussiaInstitute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, RussiaCu-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<i>H</i>-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.https://www.mdpi.com/1420-3049/27/10/31911,2,3-triazoles1,3-diynesazide–alkyne cycloadditionSonogashira cross-couplingfluorescencebioimaging |
| spellingShingle | Anastasia I. Govdi Polina V. Tokareva Andrey M. Rumyantsev Maxim S. Panov Johannes Stellmacher Ulrike Alexiev Natalia A. Danilkina Irina A. Balova 4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications Molecules 1,2,3-triazoles 1,3-diynes azide–alkyne cycloaddition Sonogashira cross-coupling fluorescence bioimaging |
| title | 4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications |
| title_full | 4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications |
| title_fullStr | 4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications |
| title_full_unstemmed | 4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications |
| title_short | 4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications |
| title_sort | 4 5 bis arylethynyl 1 2 3 triazoles a new class of fluorescent labels synthesis and applications |
| topic | 1,2,3-triazoles 1,3-diynes azide–alkyne cycloaddition Sonogashira cross-coupling fluorescence bioimaging |
| url | https://www.mdpi.com/1420-3049/27/10/3191 |
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