Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against <i>Botrytis cinerea</i> of (<i>E</i>)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol (Pyridine Schiff Base)
<i>Botrytis cinerea</i> is a ubiquitous necrotrophic filamentous fungal phytopathogen that lacks host specificity and can affect more than 1000 different plant species. In this work, we explored <b>L1</b> [(<i>E</i>)-2-{[(2-aminopyridin-2-yl)imino]-methyl}-4,6-di-...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/12/2741 |
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| author | Alexander Carreño Dayán Páez-Hernández Plinio Cantero-López César Zúñiga Jan Nevermann Angélica Ramírez-Osorio Manuel Gacitúa Poldie Oyarzún Felipe Sáez-Cortez Rubén Polanco Carolina Otero Juan A. Fuentes |
| author_facet | Alexander Carreño Dayán Páez-Hernández Plinio Cantero-López César Zúñiga Jan Nevermann Angélica Ramírez-Osorio Manuel Gacitúa Poldie Oyarzún Felipe Sáez-Cortez Rubén Polanco Carolina Otero Juan A. Fuentes |
| author_sort | Alexander Carreño |
| collection | DOAJ |
| description | <i>Botrytis cinerea</i> is a ubiquitous necrotrophic filamentous fungal phytopathogen that lacks host specificity and can affect more than 1000 different plant species. In this work, we explored <b>L1</b> [(<i>E</i>)-2-{[(2-aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol], a pyridine Schiff base harboring an intramolecular bond (IHB), regarding their antifungal activity against <i>Botrytis cinerea</i>. Moreover, we present a full characterization of the <b>L1</b> by NMR and powder diffraction, as well as UV–vis, in the presence of previously untested different organic solvents. Complementary time-dependent density functional theory (TD-DFT) calculations were performed, and the noncovalent interaction (NCI) index was determined. Moreover, we obtained a scan-rate study on cyclic voltammetry of <b>L1</b>. Finally, we tested the antifungal activity of <b>L1</b> against two strains of <i>Botrytis cinerea</i> (B05.10, a standard laboratory strain; and A1, a wild type strains isolated from Chilean blueberries). We found that <b>L1</b> acts as an efficient antifungal agent against <i>Botrytis cinerea</i> at 26 °C, even better than the commercial antifungal agent fenhexamid. Although the antifungal activity was also observed at 4 °C, the effect was less pronounced. These results show the high versatility of this kind of pyridine Schiff bases in biological applications. |
| first_indexed | 2024-03-10T19:12:11Z |
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| id | doaj.art-801d68c7624d49d88cf6876bb3586b1d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:12:11Z |
| publishDate | 2020-06-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-801d68c7624d49d88cf6876bb3586b1d2023-11-20T03:42:13ZengMDPI AGMolecules1420-30492020-06-012512274110.3390/molecules25122741Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against <i>Botrytis cinerea</i> of (<i>E</i>)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol (Pyridine Schiff Base)Alexander Carreño0Dayán Páez-Hernández1Plinio Cantero-López2César Zúñiga3Jan Nevermann4Angélica Ramírez-Osorio5Manuel Gacitúa6Poldie Oyarzún7Felipe Sáez-Cortez8Rubén Polanco9Carolina Otero10Juan A. Fuentes11Center of Applied Nanosciences (CANS), Facultad de Ciencias Exactas, Universidad Andres Bello, República 330, Santiago 8370186, ChileCenter of Applied Nanosciences (CANS), Facultad de Ciencias Exactas, Universidad Andres Bello, República 330, Santiago 8370186, ChileCenter of Applied Nanosciences (CANS), Facultad de Ciencias Exactas, Universidad Andres Bello, República 330, Santiago 8370186, ChileInstituto de Ciencias Naturales, Facultad de Medicina Veterinaria y Agronomía, Universidad de Las Américas, Sede Providencia, Manuel Montt 948, Santiago 7500972, ChileLaboratorio de Genética y Patogénesis Bacteriana, Facultad de Ciencias de la Vida, Universidad Andres Bello, República 330, Santiago 8370186, ChileFONDECYT de Inicio, Facultad de Ciencias Exactas, Universidad Andres Bello, República 330, Santiago 8370186, ChileFacultad de Química y Biología, USACH, Av. L.B. O’Higgins 3363, Santiago 7254758, ChileLaboratorio de Análisis de Sólido (LAS), Facultad de Ingeniería y Facultad de Ciencias Exactas, Universidad Andrés Bello, República 330, Santiago 8370186, ChileCentro de Biotecnología Vegetal (CBV), Laboratorio de Fitopatógenos Fúngicos, Facultad de Ciencias de la Vida, Universidad Andres Bello, República 330, Santiago 8370186, ChileCentro de Biotecnología Vegetal (CBV), Laboratorio de Fitopatógenos Fúngicos, Facultad de Ciencias de la Vida, Universidad Andres Bello, República 330, Santiago 8370186, ChileEscuela de Química y Farmacia, Facultad de Medicina, Universidad Andres Bello, República 252, Santiago 8320000, ChileLaboratorio de Genética y Patogénesis Bacteriana, Facultad de Ciencias de la Vida, Universidad Andres Bello, República 330, Santiago 8370186, Chile<i>Botrytis cinerea</i> is a ubiquitous necrotrophic filamentous fungal phytopathogen that lacks host specificity and can affect more than 1000 different plant species. In this work, we explored <b>L1</b> [(<i>E</i>)-2-{[(2-aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol], a pyridine Schiff base harboring an intramolecular bond (IHB), regarding their antifungal activity against <i>Botrytis cinerea</i>. Moreover, we present a full characterization of the <b>L1</b> by NMR and powder diffraction, as well as UV–vis, in the presence of previously untested different organic solvents. Complementary time-dependent density functional theory (TD-DFT) calculations were performed, and the noncovalent interaction (NCI) index was determined. Moreover, we obtained a scan-rate study on cyclic voltammetry of <b>L1</b>. Finally, we tested the antifungal activity of <b>L1</b> against two strains of <i>Botrytis cinerea</i> (B05.10, a standard laboratory strain; and A1, a wild type strains isolated from Chilean blueberries). We found that <b>L1</b> acts as an efficient antifungal agent against <i>Botrytis cinerea</i> at 26 °C, even better than the commercial antifungal agent fenhexamid. Although the antifungal activity was also observed at 4 °C, the effect was less pronounced. These results show the high versatility of this kind of pyridine Schiff bases in biological applications.https://www.mdpi.com/1420-3049/25/12/2741Pyridine Schiff baseintramolecular hydrogen bond<i>Botrytis cinerea</i> |
| spellingShingle | Alexander Carreño Dayán Páez-Hernández Plinio Cantero-López César Zúñiga Jan Nevermann Angélica Ramírez-Osorio Manuel Gacitúa Poldie Oyarzún Felipe Sáez-Cortez Rubén Polanco Carolina Otero Juan A. Fuentes Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against <i>Botrytis cinerea</i> of (<i>E</i>)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol (Pyridine Schiff Base) Molecules Pyridine Schiff base intramolecular hydrogen bond <i>Botrytis cinerea</i> |
| title | Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against <i>Botrytis cinerea</i> of (<i>E</i>)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol (Pyridine Schiff Base) |
| title_full | Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against <i>Botrytis cinerea</i> of (<i>E</i>)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol (Pyridine Schiff Base) |
| title_fullStr | Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against <i>Botrytis cinerea</i> of (<i>E</i>)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol (Pyridine Schiff Base) |
| title_full_unstemmed | Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against <i>Botrytis cinerea</i> of (<i>E</i>)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol (Pyridine Schiff Base) |
| title_short | Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against <i>Botrytis cinerea</i> of (<i>E</i>)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol (Pyridine Schiff Base) |
| title_sort | structural characterization dft calculation nci scan rate analysis and antifungal activity against i botrytis cinerea i of i e i 2 2 aminopyridin 2 yl imino methyl 4 6 di i tert i butylphenol pyridine schiff base |
| topic | Pyridine Schiff base intramolecular hydrogen bond <i>Botrytis cinerea</i> |
| url | https://www.mdpi.com/1420-3049/25/12/2741 |
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