Favipiravir—Tautomeric and Complexation Properties in Solution
The tautomeric properties of favipiravir were investigated experimentally for the first time by using molecular spectroscopy (UV–Vis absorption, fluorescence and NMR), as well as DFT quantum–chemical calculations. According to the obtained results, the enol tautomer is substantially more stable in m...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-12-01
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| Series: | Pharmaceuticals |
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| Online Access: | https://www.mdpi.com/1424-8247/16/1/45 |
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| author | Vera Deneva Sofia Slavova Alina Kumanova Nikolay Vassilev Daniela Nedeltcheva-Antonova Luidmil Antonov |
| author_facet | Vera Deneva Sofia Slavova Alina Kumanova Nikolay Vassilev Daniela Nedeltcheva-Antonova Luidmil Antonov |
| author_sort | Vera Deneva |
| collection | DOAJ |
| description | The tautomeric properties of favipiravir were investigated experimentally for the first time by using molecular spectroscopy (UV–Vis absorption, fluorescence and NMR), as well as DFT quantum–chemical calculations. According to the obtained results, the enol tautomer is substantially more stable in most of the organic solvents. In the presence of water, a keto form appears to be favored due to the specific solute–solvent interactions. Upon the addition of alkaline-earth-metal ions, deprotonation and complexation occurred simultaneously, giving the formation of 2 : 1 ligand : metal complexes. According to the theoretical simulations, the metal ion is captured between the carbonyl groups as a result of the size–fit effect. |
| first_indexed | 2024-03-09T11:29:29Z |
| format | Article |
| id | doaj.art-6553430ecf114a0fbf8d3170b275be04 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-09T11:29:29Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-6553430ecf114a0fbf8d3170b275be042023-11-30T23:55:00ZengMDPI AGPharmaceuticals1424-82472022-12-011614510.3390/ph16010045Favipiravir—Tautomeric and Complexation Properties in SolutionVera Deneva0Sofia Slavova1Alina Kumanova2Nikolay Vassilev3Daniela Nedeltcheva-Antonova4Luidmil Antonov5Institute of Electronics, Bulgarian Academy of Sciences, 1784 Sofia, BulgariaInstitute of Electronics, Bulgarian Academy of Sciences, 1784 Sofia, BulgariaInstitute of Electronics, Bulgarian Academy of Sciences, 1784 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 1113 Sofia, BulgariaInstitute of Electronics, Bulgarian Academy of Sciences, 1784 Sofia, BulgariaInstitute of Electronics, Bulgarian Academy of Sciences, 1784 Sofia, BulgariaThe tautomeric properties of favipiravir were investigated experimentally for the first time by using molecular spectroscopy (UV–Vis absorption, fluorescence and NMR), as well as DFT quantum–chemical calculations. According to the obtained results, the enol tautomer is substantially more stable in most of the organic solvents. In the presence of water, a keto form appears to be favored due to the specific solute–solvent interactions. Upon the addition of alkaline-earth-metal ions, deprotonation and complexation occurred simultaneously, giving the formation of 2 : 1 ligand : metal complexes. According to the theoretical simulations, the metal ion is captured between the carbonyl groups as a result of the size–fit effect.https://www.mdpi.com/1424-8247/16/1/45favipiravirCOVID-19complexationDFTUV–VisNMR |
| spellingShingle | Vera Deneva Sofia Slavova Alina Kumanova Nikolay Vassilev Daniela Nedeltcheva-Antonova Luidmil Antonov Favipiravir—Tautomeric and Complexation Properties in Solution Pharmaceuticals favipiravir COVID-19 complexation DFT UV–Vis NMR |
| title | Favipiravir—Tautomeric and Complexation Properties in Solution |
| title_full | Favipiravir—Tautomeric and Complexation Properties in Solution |
| title_fullStr | Favipiravir—Tautomeric and Complexation Properties in Solution |
| title_full_unstemmed | Favipiravir—Tautomeric and Complexation Properties in Solution |
| title_short | Favipiravir—Tautomeric and Complexation Properties in Solution |
| title_sort | favipiravir tautomeric and complexation properties in solution |
| topic | favipiravir COVID-19 complexation DFT UV–Vis NMR |
| url | https://www.mdpi.com/1424-8247/16/1/45 |
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