title: 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.
authors.affiliation: Department of Chemistry, Isfahan University of Technology, Isfahan, Iran, 84156-83111.
authors.forename: Zahra
authors.initials: Z
authors.lastname: Shokohi-Pour
authors.affiliation: Department of Chemistry, Isfahan University of Technology, Isfahan, Iran, 84156-83111. Electronic address: chinif@cc.iut.ac.ir.
authors.forename: Hossein
authors.initials: H
authors.lastname: Chiniforoshan
authors.affiliation: Student Research Committee, Nanotechnology Research Center, Department of Medical Biotechnology, School of Medicine, Mashhad University of Medical Sciences, Mashhad, Iran.
authors.forename: Amir Abbas
authors.initials: AA
authors.lastname: Momtazi-Borojeni
authors.affiliation: Department of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran.
authors.forename: Behrouz
authors.initials: B
authors.lastname: Notash
mesh_terms: D000588:Amines / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003509:Cyclohexanecarboxylic Acids / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D000077206:Gabapentin; D006801:Humans; D008024:Ligands; D013058:Mass Spectrometry; D011506:Proteins / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D005680:gamma-Aminobutyric Acid / Q000737:chemistry*
chemical_list: D000588:Amines; D000970:Antineoplastic Agents; D003509:Cyclohexanecarboxylic Acids; D008024:Ligands; D011506:Proteins; D012545:Schiff Bases; D005680:gamma-Aminobutyric Acid; D000077206:Gabapentin; D003300:Copper; D004247:DNA
keywords: Copper (II) complex; Cytotoxic activity; Gabapentin; Interaction with DNA and BSA; Schiff base