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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 5, pp 901–911 | Cite as

Synthesis and antiradical activity of novel copper(II) complexes of long chain reduced Schiff base ligands

  • Lucia Lintnerová
  • Jindra Valentová
  • Peter Herich
  • Jozef Kožíšek
  • Ferdinand Devínsky
Original Paper
  • 141 Downloads

Abstract

Oxidative stress is the cause of many diseases and at the heart of it is the overproduction of reactive oxygen species (ROS). There are several protective enzymes, e.g., superoxide dismutases (SOD), able to decrease the level of ROS in the cell; however, a therapeutic use of these enzymes is problematic. Small molecule compounds and complexes able to scavenge free radicals such as superoxide anion radicals could be used instead. These compounds are often called SOD-mimics and various researches are interested in synthesis and study of these compounds. In our study, a series of Cu(II) complexes were synthesized, containing reduced Schiff base ligands prepared from salicylaldehyde and amino acids with longer chain length (5-aminopentanoic acid, 6-aminohexanoic acid, 8-aminooctanoic acid, 11-aminoundecanoic acid, and 12-aminododecanoic acid). Complexes prepared from these ligands are novel and were prepared using three different methods. An assay based on the ability to inhibit reduction of iodonitrotetrazolium dye by superoxide anion radicals was used to determine antiradical activity of the prepared complex. Most of the prepared complexes proved to be good antiradical agents compared to cystamine and the copper(II) complex with Schiff base type ligand N-salicylidene-β-alanine. The best IC50 values of the radical transfer of the prepared compounds were two complexes of N-(2-hydroxybenzyl)-11-aminoundecanoic acid: 97.0 ± 1.9 and 45.1 ± 0.5 μM.

Graphical abstract

Keywords

Coordination chemistry Crystal structure Amino acids Ligands Reduced Schiff bases Antiradical activity 

Notes

Acknowledgements

This work was supported by the Slovak Research and Development Agency under Contract no. APVV-0516-12 and no. APVV-15-0079 and Scientific Grant Agency of the Slovak Republic VEGA (Project no. 1/0871/16 and 1/0346/16).

Supplementary material

706_2017_2137_MOESM1_ESM.docx (793 kb)
Supplementary material 1 (DOCX 792 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemical Theory of Drugs, Faculty of PharmacyComenius University in BratislavaBratislavaSlovak Republic
  2. 2.Department of Physical ChemistrySlovak University of TechnologyBratislavaSlovak Republic

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