Synthesis, Spectroscopic Characterization, Catalytic and Biological Activity of Oxidovanadium(V) Complexes with Chiral Tetradentate Schiff Bases
New oxidovanadium(V) complexes, <b>VOL<sup>1</sup></b>–<b>VOL<sup>10</sup></b>, with chiral tetradentate Schiff bases obtained by monocondensation reaction of salicylaldehyde derivatives with 1<i>S</i>,2<i>S</i>-(+)-2-amino-1-(4...
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MDPI AG
2023-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/21/7408 |
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| author | Grzegorz Romanowski Justyna Budka Iwona Inkielewicz-Stepniak |
| author_facet | Grzegorz Romanowski Justyna Budka Iwona Inkielewicz-Stepniak |
| author_sort | Grzegorz Romanowski |
| collection | DOAJ |
| description | New oxidovanadium(V) complexes, <b>VOL<sup>1</sup></b>–<b>VOL<sup>10</sup></b>, with chiral tetradentate Schiff bases obtained by monocondensation reaction of salicylaldehyde derivatives with 1<i>S</i>,2<i>S</i>-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol. All complexes have been characterized using different spectroscopic methods, viz. IR, UV-Vis, circular dichroism, one- (<sup>1</sup>H, <sup>51</sup>V) and two-dimensional (COSY, NOESY) NMR spectroscopy, and elemental analysis. Furthermore, the catalytic ability of all compounds in the epoxidation of styrene, cyclohexene, and its naturally occurring monoterpene derivatives, i.e., <i>S</i>(−)-limonene and (−)-α-pinene has also been studied, using two different oxidants, i.e., aqueous 30% H<sub>2</sub>O<sub>2</sub> or <i>tert</i>-butyl hydroperoxide (TBHP). In addition, the biological properties of these chiral oxidovanadium(V) compounds, but also <i>cis</i>-dioxidomolybdenum(VI) complexes with the same chiral Schiff bases, were studied. Their cytotoxic and cytoprotective activity studies with the HT-22 hippocampal neuronal cells revealed a concentration-dependent effect in the range of 10–100 μM. Moreover, vanadium(V) complexes, in contrast to <i>cis</i>-dioxidomolybdenum(VI) compounds, demonstrated higher cytotoxicity and lack of cytoprotective ability against H<sub>2</sub>O<sub>2</sub>-induced cytotoxicity. |
| first_indexed | 2024-03-11T11:24:35Z |
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| language | English |
| last_indexed | 2024-03-11T11:24:35Z |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a9cfef37392e4286876f6038388276572023-11-10T15:08:54ZengMDPI AGMolecules1420-30492023-11-012821740810.3390/molecules28217408Synthesis, Spectroscopic Characterization, Catalytic and Biological Activity of Oxidovanadium(V) Complexes with Chiral Tetradentate Schiff BasesGrzegorz Romanowski0Justyna Budka1Iwona Inkielewicz-Stepniak2Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, PL-80308 Gdansk, PolandDepartment of Pharmaceutical Pathophysiology, Faculty of Pharmacy, Medical University of Gdansk, Dębinki 7, Building 27, PL-80211 Gdansk, PolandDepartment of Pharmaceutical Pathophysiology, Faculty of Pharmacy, Medical University of Gdansk, Dębinki 7, Building 27, PL-80211 Gdansk, PolandNew oxidovanadium(V) complexes, <b>VOL<sup>1</sup></b>–<b>VOL<sup>10</sup></b>, with chiral tetradentate Schiff bases obtained by monocondensation reaction of salicylaldehyde derivatives with 1<i>S</i>,2<i>S</i>-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol. All complexes have been characterized using different spectroscopic methods, viz. IR, UV-Vis, circular dichroism, one- (<sup>1</sup>H, <sup>51</sup>V) and two-dimensional (COSY, NOESY) NMR spectroscopy, and elemental analysis. Furthermore, the catalytic ability of all compounds in the epoxidation of styrene, cyclohexene, and its naturally occurring monoterpene derivatives, i.e., <i>S</i>(−)-limonene and (−)-α-pinene has also been studied, using two different oxidants, i.e., aqueous 30% H<sub>2</sub>O<sub>2</sub> or <i>tert</i>-butyl hydroperoxide (TBHP). In addition, the biological properties of these chiral oxidovanadium(V) compounds, but also <i>cis</i>-dioxidomolybdenum(VI) complexes with the same chiral Schiff bases, were studied. Their cytotoxic and cytoprotective activity studies with the HT-22 hippocampal neuronal cells revealed a concentration-dependent effect in the range of 10–100 μM. Moreover, vanadium(V) complexes, in contrast to <i>cis</i>-dioxidomolybdenum(VI) compounds, demonstrated higher cytotoxicity and lack of cytoprotective ability against H<sub>2</sub>O<sub>2</sub>-induced cytotoxicity.https://www.mdpi.com/1420-3049/28/21/7408vanadiumSchiff basecatalysisbiological activity |
| spellingShingle | Grzegorz Romanowski Justyna Budka Iwona Inkielewicz-Stepniak Synthesis, Spectroscopic Characterization, Catalytic and Biological Activity of Oxidovanadium(V) Complexes with Chiral Tetradentate Schiff Bases Molecules vanadium Schiff base catalysis biological activity |
| title | Synthesis, Spectroscopic Characterization, Catalytic and Biological Activity of Oxidovanadium(V) Complexes with Chiral Tetradentate Schiff Bases |
| title_full | Synthesis, Spectroscopic Characterization, Catalytic and Biological Activity of Oxidovanadium(V) Complexes with Chiral Tetradentate Schiff Bases |
| title_fullStr | Synthesis, Spectroscopic Characterization, Catalytic and Biological Activity of Oxidovanadium(V) Complexes with Chiral Tetradentate Schiff Bases |
| title_full_unstemmed | Synthesis, Spectroscopic Characterization, Catalytic and Biological Activity of Oxidovanadium(V) Complexes with Chiral Tetradentate Schiff Bases |
| title_short | Synthesis, Spectroscopic Characterization, Catalytic and Biological Activity of Oxidovanadium(V) Complexes with Chiral Tetradentate Schiff Bases |
| title_sort | synthesis spectroscopic characterization catalytic and biological activity of oxidovanadium v complexes with chiral tetradentate schiff bases |
| topic | vanadium Schiff base catalysis biological activity |
| url | https://www.mdpi.com/1420-3049/28/21/7408 |
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