Evaluation of in vitro antibacterial, DNA binding, DNA damage, DFT and antioxidant studies of aminobenzaldehyde-based heterocyclic Schiff base derivatives

Abstract

Heterocyclic Schiff base derivatives have been synthesized by condensation of dimethylaminobenzaldehyde and substituted amines in 1:1 molar ratio. Synthesized heterocyclic Schiff base derivatives (3a-3h) were structurally characterized by UV-visible, IR, 1 H and 13 C NMR spectroscopy, elemental analysis and mass spectrometry. Antibacterial property of heterocyclic Schiff base derivatives has been explored against Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Staphylococcus aureus using disc diffusion method. Results revealed that Schiff base derivatives 3c, 3f and 3h have signi cant antibacterial activity against tested bacterial strains. Heterocyclic Schiff base derivatives also explored for DNA binding interactions study with calf thymus-DNA (Ct-DNA) by absorption spectroscopy, uorescence measurements, circular dichroism, viscosity measurement and molecular docking study. Heterocyclic Schiff base derivatives 3c, 3f and 3h bind with Ct-DNA through groove binding mode with (K b ) 1.62 × 10 4 , 1.58 × 10 4 M -1 and 2.3 × 10 4 M -1 respectively. Molecular docking the target compounds was also studied against B-DNA dodecamer d(CGCGAATTCGCG) 2.Agarose gel electrophoresis study revealed that after the addition of compounds 3c, 3f and 3h, DNA damage induced by free radical has been inhibited. Antioxidant potential of heterocyclic Schiff base derivatives was also estimated by Diphenyl-1-picryl-hydrazyl (DPPH) free radical and hydrogen peroxide assay. The experimental results of the spectral properties of the synthesized derivatives 3c, 3f and 3h in solution were interpreted at the molecular level with aid of the DFT and TD-DFT/CAM-B3LYP/6-31+G(d) computational methods with Becke-3-Lee-Yang-Parr(B3LYP) exchange-correlation functional approach. Research HighlightsBioactive Schiff base were synthesized and characterized.Potent compounds showed signi cant antibacterial activity.Synthesized compounds interact with Ct-DNA through electrostatic mode of binding.Molecular docking study also con rms the binding nature of the compounds with DNA.Heterocyclic compound can also be used as signi cant antioxidant agents.DFT of the potent compounds has been also carried out for the optimization of geometry and spectroscopic data.