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  2. Oxidovanadium(V) Schiff Base Complexes Derived from Chiral 3-amino-1,2-propanediol Enantiomers: Synthesis, Spectroscopic Studies, Catalytic and Biological Activity

Oxidovanadium(V) Schiff Base Complexes Derived from Chiral 3-amino-1,2-propanediol Enantiomers: Synthesis, Spectroscopic Studies, Catalytic and Biological Activity

  • Int J Mol Sci. 2024 May 3;25(9):5010. doi: 10.3390/ijms25095010.
Grzegorz Romanowski 1 Justyna Budka 2 Iwona Inkielewicz-Stepniak 2
Affiliations

Affiliations

  • 1 Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, PL-80308 Gdansk, Poland.
  • 2 Department of Pharmaceutical Pathophysiology, Faculty of Pharmacy, Medical University of Gdansk, Dębinki 7, Building 27, PL-80211 Gdansk, Poland.
Abstract

Oxidovanadium(V) complexes, [(+)VOL1-5] and [(-)VOL1-5], with chiral tetradentate Schiff Bases, which are products of monocondensation of S(‒)-3-amino-1,2-propanediol or R(+)-3-amino-1,2-propanediol with salicylaldehyde derivatives, have been synthesized. Different spectroscopic methods, viz. 1H and 51V NMR, IR, UV-Vis, and circular dichroism, as well as elemental analysis, have been used for their detailed characterization. Furthermore, the epoxidation of styrene, cyclohexene, and two monoterpenes, S(‒)-limonene and (‒)-α-pinene, using two oxidants, aqueous 30% H2O2 or tert-butyl hydroperoxide (TBHP) in decane, has been studied with catalytic amounts of all complexes. Finally, biological cytotoxicity studies have also been performed with these oxidovanadium(V) compounds for comparison with cis-dioxidomolybdenum(VI) Schiff base complexes with the same chiral ligands, as well as to determine the cytoprotection against the oxidative damage caused by 30% H2O2 in the HT-22 hippocampal neuronal cells in the range of their 10-100 μM concentration.

Keywords

cytoprotection; cytotoxicity; epoxidation; vanadium.

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