Abstract
Herein, we report facile procedures for synthesis of a new Schiff base ligand (H2L,5-Diethylamino-2-({2-[(2-hydroxy-benzylidene)-amino]-phenylimino}-methyl)-phenol) and its Ag(I), Pd(II) and Cu(II) complexes. The structure of the H2L ligand as well as its metal complexes was deduced based on wide range of analytical, structural and spectroscopic tools, along with theoretical evidence via density functional theory (DFT) calculations. The obtained results indicated that the Schiff base (H2L) ligand acts as a tetradentate N2O2 donor with two azomethine nitrogen’s (N1, N2) and two deprotonated phenolic oxygens (O1, O2) atoms. A distorted octahedral structure is assigned to [CuL(OH2)2]·3/2H2O complex and square planar structure for PdL and AgL complexes. The electronic structure and non-linear optical (NLO) property of the prepared compounds were discussed theoretically by the B3LYP/GENECP program. Results revealed that all complexes have non-planner geometries as indicated from the dihedral angles. The charge transfer occurs within the synthesized complexes as indicated from the calculated energy gap between HOMO and LUMO energies. The H2L ligand and its complexes are excellent candidates for NLO materials as implied from their hyperpolarizabilities and polarizabilities values. The biological activities of the prepared complexes against selected microorganisms and cancer cell lines gave good growth inhibitory effect. The biocidal potencies of the ligand and its complexes can be arranged as follows: AgL > CuL > PdL > H2L, as compared to the used standard drugs. The antiproliferative activity of the studied complexes against different carcinoma cell lines such as liver (Hep-G2), breast (MCF-7) and colon (HCT-116) followed the order H2L < AgL< PdL < CuL < vinblastine. Probing the binding interactions of prepared complexes with calf thymus (CT)-DNA using electronic absorption, gel electrophoresis and viscosity measurements revealed strong interaction via intercalation modes, as also evidenced by their molecular docking study.
Highlights
One of the major health crises of today’s world is antimicrobial drug resistance
Motivated by the promising structural and biological properties of Schiff based metal complexes together with our perpetual engagement in this kind of research endeavor [14,15,16,17,18], here, we offer a facile approach for the synthesis and characterization of a novel tetradentate (N2 O2 ) Schiff base ligand (H2 L), (L = 5-Diethylamino-2-({2-[(2-hydroxy-benzylidene)-amino]-phenylimino}-methyl)-phenol), and its metal complexes with Ag(I), Pd(II) and Cu(II) ions
The 1 H-NMR data for the Schiff base was recorded by using dimethyl sulfoxide (DMSO)-d6 as a solvent and the chemical shift in ppm
Summary
One of the major health crises of today’s world is antimicrobial drug resistance. To tackle it, there is an immediate requirement for the development of new and much safer drugs and the present work is one such quest for novel and efficient drug candidates. Schiff base compounds are an important class of ligands that have attracted a great deal of interest owing to their rich coordination chemistry [1,2]. These compounds have extensive applications in different fields. Motivated by the promising structural and biological properties of Schiff based metal complexes together with our perpetual engagement in this kind of research endeavor [14,15,16,17,18], here, we offer a facile approach for the synthesis and characterization of a novel tetradentate (N2 O2 ) Schiff base ligand (H2 L), (L = 5-Diethylamino-2-({2-[(2-hydroxy-benzylidene)-amino]-phenylimino}-methyl)-phenol), and its metal complexes with Ag(I), Pd(II) and Cu(II) ions.
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