Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers
A new method for the synthesis of azido-propargyloxy derivatives of 1,3,5-triazine has been developed utilizing the nitrosation of hydrazyno-1,3,5-triazines. New hydrazines (2-hydrazino-4,6-bis(propargyloxy)-1,3,5-triazine and 2,4-dihydrazino-6-propargyloxy-1,3,5-triazine) were synthesized and chara...
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MDPI AG
2023-12-01
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| author | Anna V. Tsyganova Artem O. Petrov Alexey V. Shastin Natalia V. Filatova Victoria A. Mumyatova Alexander E. Tarasov Alina V. Lolaeva Georgiy V. Malkov |
| author_facet | Anna V. Tsyganova Artem O. Petrov Alexey V. Shastin Natalia V. Filatova Victoria A. Mumyatova Alexander E. Tarasov Alina V. Lolaeva Georgiy V. Malkov |
| author_sort | Anna V. Tsyganova |
| collection | DOAJ |
| description | A new method for the synthesis of azido-propargyloxy derivatives of 1,3,5-triazine has been developed utilizing the nitrosation of hydrazyno-1,3,5-triazines. New hydrazines (2-hydrazino-4,6-bis(propargyloxy)-1,3,5-triazine and 2,4-dihydrazino-6-propargyloxy-1,3,5-triazine) were synthesized and characterized via FTIR, NMR spectroscopy and elemental analysis. The hyperbranched polymers with azide (diazide monomer) and propargyloxy terminal groups were obtained via the azide-alkyne polycycloaddition reaction of diazide and monoazide AB<sub>2</sub>-type monomers. The antibacterial activity against <i>Escherichia coli</i> bacteria of 2,4,6-trispropargyloxy-1,3,5-triazine, 2-azido-4,6-bispropargyloxy-1,3,5-triazine, and 2,4-diazido-6-propargyloxy-1,3,5-triazine and their hyperbranched polymers was studied. Only 2,4-diazido-6-propargyloxy-1,3,5-triazine has weak antibacterial activity in comparison with ampicillin. The cytotoxicity of these compounds against M-HeLa, FetMSC, and Vero cell lines was also studied. 2,4,6-trispropargyloxy-1,3,5-triazine does not show any cytotoxic effect (IC<sub>50</sub> ≥ 280 µM). It was shown that the presence of an azide group in the compound directly affects the cytotoxic effect. Hyperbranched polymers have a less cytotoxic effect against M-HeLa (IC<sub>50</sub> > 100) in comparison with monomers (IC<sub>50</sub> = 90–99 µM). This makes it possible to use these polymers as the basis for biocompatible materials in biomedical applications. |
| first_indexed | 2024-03-07T22:38:13Z |
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| institution | Directory Open Access Journal |
| issn | 2624-8549 |
| language | English |
| last_indexed | 2024-03-07T22:38:13Z |
| publishDate | 2023-12-01 |
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| spelling | doaj.art-f0c58e09cda248dc8a3dcea7fb65d0872024-02-23T15:12:05ZengMDPI AGChemistry2624-85492023-12-016111210.3390/chemistry6010001Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched PolymersAnna V. Tsyganova0Artem O. Petrov1Alexey V. Shastin2Natalia V. Filatova3Victoria A. Mumyatova4Alexander E. Tarasov5Alina V. Lolaeva6Georgiy V. Malkov7Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, RussiaA new method for the synthesis of azido-propargyloxy derivatives of 1,3,5-triazine has been developed utilizing the nitrosation of hydrazyno-1,3,5-triazines. New hydrazines (2-hydrazino-4,6-bis(propargyloxy)-1,3,5-triazine and 2,4-dihydrazino-6-propargyloxy-1,3,5-triazine) were synthesized and characterized via FTIR, NMR spectroscopy and elemental analysis. The hyperbranched polymers with azide (diazide monomer) and propargyloxy terminal groups were obtained via the azide-alkyne polycycloaddition reaction of diazide and monoazide AB<sub>2</sub>-type monomers. The antibacterial activity against <i>Escherichia coli</i> bacteria of 2,4,6-trispropargyloxy-1,3,5-triazine, 2-azido-4,6-bispropargyloxy-1,3,5-triazine, and 2,4-diazido-6-propargyloxy-1,3,5-triazine and their hyperbranched polymers was studied. Only 2,4-diazido-6-propargyloxy-1,3,5-triazine has weak antibacterial activity in comparison with ampicillin. The cytotoxicity of these compounds against M-HeLa, FetMSC, and Vero cell lines was also studied. 2,4,6-trispropargyloxy-1,3,5-triazine does not show any cytotoxic effect (IC<sub>50</sub> ≥ 280 µM). It was shown that the presence of an azide group in the compound directly affects the cytotoxic effect. Hyperbranched polymers have a less cytotoxic effect against M-HeLa (IC<sub>50</sub> > 100) in comparison with monomers (IC<sub>50</sub> = 90–99 µM). This makes it possible to use these polymers as the basis for biocompatible materials in biomedical applications.https://www.mdpi.com/2624-8549/6/1/11,3,5-triazinenucleophilic substitutionazido-acetylene cycloadditionhyperbranched polymersantibacterial activitycytotoxicity |
| spellingShingle | Anna V. Tsyganova Artem O. Petrov Alexey V. Shastin Natalia V. Filatova Victoria A. Mumyatova Alexander E. Tarasov Alina V. Lolaeva Georgiy V. Malkov Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers Chemistry 1,3,5-triazine nucleophilic substitution azido-acetylene cycloaddition hyperbranched polymers antibacterial activity cytotoxicity |
| title | Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers |
| title_full | Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers |
| title_fullStr | Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers |
| title_full_unstemmed | Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers |
| title_short | Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers |
| title_sort | synthesis antibacterial activity and cytotoxicity of azido propargyloxy 1 3 5 triazine derivatives and hyperbranched polymers |
| topic | 1,3,5-triazine nucleophilic substitution azido-acetylene cycloaddition hyperbranched polymers antibacterial activity cytotoxicity |
| url | https://www.mdpi.com/2624-8549/6/1/1 |
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