Synthesis, characterization, in vitro, in silico and in vivo investigations and biological assessment of Knoevenagel condensate β-diketone Schiff base transition metal complexes

Abstract

A novel Schiff base ligand was synthesized by the Knoevenagel condensation of β-diketone (obtained from substituted Curcumin and Cuminaldehyde) and 4-amino antipyrine. Metal complexes were made from this Schiff base by reacting with metal salts such as Cu(II), Ni(II), Ru(III), VO(IV), and Ce(IV). Physicochemical approaches such as UV-Vis, FT-IR, NMR, EPR, and Mass spectroscopy were used to determine the geometry of the complexes. The thermodynamic stability and biological accessibility of the complexes were investigated using density functional theory (DFT) calculations at the B3LYP/6-31G(d) level. A molecular docking analysis was also performed on 1BNA receptor. Both the Schiff base ligand and metal complexes interacted well to this protein receptor. All metal complexes have a significant potential to bind to CT DNA via the intercalation mechanism. All the in vivo and in vitro screening studies showed that the complexes exhibit higher activities than the free Schiff base. Communicated by Ramaswamy H. Sarma