Synthesis, characterization, DNA-binding, and antioxidant activities of four copper(II) complexes containing N-(3-hydroxybenzyl)-amino amide ligands

Abstract

Four new substituted amino acid ligands, N-(3-hydroxybenzyl)-glycine acid (HL₁), N-(3-hydroxybenzyl)-alanine acid (HL₂), N-(3-hydroxybenzyl)-phenylalanine acid (HL₃), and N-(3-hydroxybenzyl)-leucine acid (HL₄), were synthesized and characterized on the basis of ¹H NMR, IR, ESI-MS, and elemental analyses. The crystal structures of their copper(II) complexes [Cu(L₁)₂]·2H₂O (1), [Cu(L₂)₂(H₂O)] (2), [Cu(L₃)₂(CH₃OH)] (3), and [Cu(L₄)₂(H₂O)]·H₂O (4) were determined by X-ray diffraction analysis. The ligands coordinate with copper(II) through secondary amine and carboxylate in all complexes. In 2, 3, and 4, additional water or methanol coordinates, completing a distorted tetragonal pyramidal coordination geometry around copper. Fluorescence titration spectra, electronic absorption titration spectra, and EB displacement indicate that all the complexes bind to CT-DNA. Intrinsic binding constants of the copper(II) complexes with CT-DNA are 1.32 × 10⁶M⁻¹, 4.32 × 10⁵M⁻¹, 5.00 × 10⁵M⁻¹, and 5.70 × 10⁴M⁻¹ for 1, 2, 3, and 4, respectively. Antioxidant activities of the compounds have been investigated by spectrophotometric measurements. The results show that the Cu(II) complexes have similar superoxide dismutase activity to that of native Cu, Zn-SOD.

Keywords:

• Substituted amino acid ligand
• Copper(II) complex
• Crystal structure
• DNA Binding
• Antioxidant activity

Acknowledgement

This work was supported by the National Science Foundation of China (21001040).