Green synthesis of nanosized N,N'-bis(1-naphthylidene)-4,4'-diaminodiphenylmethane and its metal (II) complexes and evaluation of their biological activity

Abstract

Condensation of ecofriendly synthesized 4,4’-methanedianiline with 2-hydroxy-1-naphthaldehyde produced a (1:1) octopus-like Schiff base mixed ligand. Reaction with Co(OAc)2⋅H2O, NiCl2⋅6H2O, Cu(OAc)2⋅H2O and Zn(OAc)2⋅2H2O metals furnished their complexes in high yield and purity. All new structures were fully characterized by various spectroscopic and spectrometric measurements. The complexes exhibited high thermal stability up to 700 °C, leaving nearly 40% of their mass as residues. Antimicrobial screening results exhibited moderate activities towards all studied microbes. Antioxidant screening was concentration dependent, and their activities were in the order Ni(II) > Zn(II) > Cu(II) > Co(II) complexes. The NO inhibitory effect revealed that the nickel complex exhibited the highest activity, whereas the cobalt complex showed the lowest inhibition. All compounds showed a significant lipid peroxidation inhibitory effect against oxidative stress. The complexes significantly diminished the TBARS level, and the nickel complex exhibited the highest inhibition at p < 0.01. Antioxidants stress the oxidative damage induced by iron, indicating that the nickel complex has the highest reducing activity. The inhibitory effect against acetylcholine esterase showed that the copper complex has the highest activity. Membrane stabilization activities clearly indicated that most compounds can improve the integrity of the cells and stability of their membrane, and this result may be related to their antioxidant capacity to protect against cytotoxicity. The nickel complex exhibited a stronger total antioxidant capacity than the other complexes. The biological and antioxidant capacities of these complexes may make them promising candidates in pharmaceutical applications.