A novel Schiff base derived from the gabapentin drug and copper (II) complex: Synthesis, characterization, interaction with DNA/protein and cytotoxic activity

Abstract

A novel Schiff base [C20H23NO3], has been prepared and characterized using FT-IR, UV-vis, (1)H NMR spectroscopy, elemental analysis and X-ray crystallography. A copper (II) complex [Cu(C20H22NO3)2]·H2O has also been synthesized and characterized. The new ligand and complex thus obtained were investigated by their interaction with calf thymus DNA and BSA using electronic absorption spectroscopy, fluorescence spectroscopy, and thermal denaturation. The intrinsic binding constants Kb of the ligand and Cu (II) complex, with CT-DNA obtained from UV-vis absorption studies were 1.53×10(4)M(-1) and 3.71×10(5)M(-1), respectively. Moreover the addition of the two compounds to CT-DNA (1:2) led to an increase of the melting temperature of DNA up to around 2.61°C for the ligand and 3.99°C for the Cu (II) complex. The ligand and Cu (II) complex bind to CT-DNA via a partial intercalative, as shown by the experimental data. In addition, the albumin interactions of the two compounds were studied by fluorescence quenching spectra, the results indicating that the binding mechanism is a static quenching process. The in vitro cytotoxicity of the two compounds on three different cancer cell lines was evaluated by MTT assay. The results showed that the copper complex exerted enhanced cytotoxicity compared with the Schiff base ligand; thereby, this complex clearly implies a positive synergistic effect. Furthermore, the copper complex showed a high, selective, and dose-dependent cytotoxicity against cancer cell lines.

Metal complexes in cancer therapy – an update from drug design perspective

“…The complex was investigated for its interaction with calf thymus DNA and bovine serum albumin using spectroscopic methods. The results revealed that the binding mechanism is a static quenching process 57. The in vitro cytotoxic evaluation study was conducted using MTT assay, and the result revealed that a copper complex exhibited enhanced cytotoxicity, high selectivity and dose-dependent cytotoxicity 57…”

Schiff Base Metal Complexes as Anticancer Agents

“…Investigated results showed that copper complex (Fig. 4) show positive synergic effect and high selective in dose dependent manner [13].…”

“…New Schiff base ligand with molecular formula (C 20 H 23 NO 3 ), has been prepared and treated with copper metal [13]. The copper metal complex was screened for spectroscopic analyses.…”

Spectroscopic studies, structural characterization and electrochemical studies of two cobalt (III) complexes with tridentate hydrazone Schiff base ligands: Evaluation of antibacterial activities, DNA‐binding, BSA interaction and molecular docking

“…The interaction of ligands and complexes ( 1 ) and ( 2 ) with DNA has been recorded by the use of MB. MB is a well‐known intercalator and tricyclic that is often used as a spectral probe to establish the mode of binding of small molecules to double‐helical DNA. The emission spectra of the MB‐DNA solution are shown in Figure by the addition of various amounts of ligands and complexes ( 1 ) and ( 2 ).…”