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.

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.

MeSH terms

  • Animals
  • Catalysis
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology
  • Humans
  • Mice
  • Oxidative Stress / drug effects
  • Schiff Bases* / chemical synthesis
  • Schiff Bases* / chemistry
  • Schiff Bases* / pharmacology
  • Stereoisomerism
  • Vanadium / chemistry

Substances

  • Schiff Bases
  • Vanadium
  • Coordination Complexes

Grants and funding

This scientific work was supported by the grant ST-54 from the Medical University of Gdansk and the Polish Ministry of Science and Higher Education (Grant No. 531-T050-D840-24).