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

Shokohi-Pour, Z. and Chiniforoshan, H. and Momtazi-Borojeni, A. A. and Notash, B. (2016) A novel Schiff base derived from the gabapentin drug and copper (II) complex: Synthesis, characterization, interaction with DNA/protein and cytotoxic activity. Journal of Photochemistry and Photobiology B: Biology, 162. pp. 34-44.

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Abstract

A novel Schiff base C20H23NO3, has been prepared and characterized using FT-IR, UV-vis, 1H 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 × 104 M- 1 and 3.71 × 105 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. © 2016 Published by Elsevier B.V.

Item Type: Article
Additional Information: Cited By :34 Export Date: 16 February 2020 CODEN: JPPBE Correspondence Address: Chiniforoshan, H.; Department of Chemistry, Isfahan University of TechnologyIran; email: chinif@cc.iut.ac.ir
Uncontrolled Keywords: Copper (II) complex Cytotoxic activity Gabapentin Interaction with DNA and BSA Schiff base albumin copper complex cytotoxic agent DNA double stranded DNA 4 aminobutyric acid amine antineoplastic agent copper cyclohexanecarboxylic acid derivative ligand protein absorption spectroscopy antineoplastic activity Article binding affinity cancer cell line controlled study cytotoxicity denaturation DNA denaturation DNA helix drug binding site drug DNA interaction drug protein binding drug selectivity drug synthesis energy transfer fluorescence spectroscopy human human cell IC50 in vitro study ionic strength jurkat cell line peripheral blood mononuclear cell pH priority journal proton nuclear magnetic resonance SKOV3 cell line U87 cell line X ray crystallography X ray diffraction chemistry drug screening infrared spectroscopy mass spectrometry tumor cell line ultraviolet spectrophotometry Amines Antineoplastic Agents Cell Line, Tumor Crystallography, X-Ray Cyclohexanecarboxylic Acids Drug Screening Assays, Antitumor gamma-Aminobutyric Acid Humans Ligands Proteins Schiff Bases Spectrophotometry, Ultraviolet Spectroscopy, Fourier Transform Infrared
Subjects: QV pharmacology
Divisions: Mashhad University of Medical Sciences
Depositing User: mr lib4 lib4
Date Deposited: 26 Feb 2020 10:12
Last Modified: 26 Feb 2020 10:12
URI: http://eprints.mums.ac.ir/id/eprint/13215

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