Schiff-base ligands containing phenanthroline terminals: Synthesis, characterization, biological activities and molecular docking study

Abstract

Three new phenanthroline-derived ligands were synthesized by the Schiff base condensation method. The first ligand was the result of 1,10-phenanthroline-2-carboxyaldehyde reaction with 1,4-diaminobutane (L1). The other ligands were obtained 1,6-diaminohexane (L2) and 1,8-diaminooctane (L3) with the phenanthroline aldehyde in separate reactions. The structures of all ligands were elucidated using spectral techniques such as FT-IR, 13C NMR, 1H NMR and LC ESI/MS. The geometric properties of ligands such as bond lengths, bond angles, dihedral angles, electronic properties, HOMO and LUMO energies were calculated by using the Gaussian 09w programme. Ligands were optimized with B3LYP and 6–311++G(2d,p) basis set and NMR and FT-IR spectra were calculated. Experimental and theoretical spectrum data were compared. All of the ligands showed antibacterial activity against Staphylococcus aureus ATCC 25923 and Bacillus cereus ATCC 11778. The anticancer activities of the ligands were also determined against human breast cancer (MCF7) and prostate cancer (DU145) cell lines. In addition, which conformation of the ligands was determined by the theoretical calculations. Docking studies of ligands with bovine serum albumin (BSA) were performed using Autock Tools 1.5.6 programme.