Synthesis, characterization, and anticancer activity of some metal complexes with a new Schiff base ligand

Abstract

A new Schiff base ligand, 2-(( E )-((4-((( E )-benzylidene)amino)phenyl)imino)methyl)-naphthalene-1-ol, was prepared by the reflux condensation of p -phenylenediamine with 2-hydroxy-1-naphthaldehyde and benzaldehyde. Metal complexes were prepared by reacting the ligand with metal salts: VCl 3 , CrCl 3 ·6H 2 O, MnCl 2 ·3H 2 O, FeCl 3 ·6H 2 O, CoCl 3 ·6H 2 O, NiCl 2 ·6H 2 O, CuCl 2 ·2H 2 O, and ZnCl 2 . The ligand and its metallic complexes were characterized by various techniques such as elemental analysis, AAS, NMR, IR, UV–Vis, TGA, DTA, XRD and TEM. The data confirmed that the ligand coordinated with the metal ions in a bidentate nature, bonding through its azomethine nitrogen atom and phenolic oxygen atom; this gave an octahedral geometry. The XRD patterns of the complexes indicated that they were of various structures: the Mn(II), Co(III), and Cu(II) complexes were triclinic, the ligand and Ni(II) complex were orthorhombic, the V(III) and Zn(II) complexes were hexagonal, the Cu(II) complex was monoclinic, and the Fe(II) complex was cubic. TEM analysis confirmed that the complexes were nanoscale in nature. The antibacterial and antifungal activities of the ligand and its complexes against Salmonella enterica serovar typhi and Candida albicans were investigated by the hole plate diffusion method. It was observed that the Co(II) and Zn(II) complexes had intermediate antibacterial activities, while the V(III) complex had the highest activity against C. albicans fungi. The in vitro anticancer activities of the ligand and its metal complexes were tested towards PC-3, SKOV3, and HeLa tumour cell lines, where they exhibited higher antitumour activities against these selected human cell lines than clinically used drugs such as cisplatin, estramustine, and etoposide.