Non-Linear Optical Property and Biological Assays of Therapeutic Potentials Under In Vitro Conditions of Pd(II), Ag(I) and Cu(II) Complexes of 5-Diethyl amino-2-({2-[(2-hydroxy-Benzylidene)-amino]-phenylimino}-methyl)-phenol

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.

Co (II), Cu (II), Mn (II), Ni (II), Pd (II), and Pt (II) complexes of bidentate Schiff base ligand: Synthesis, crystal structure, and acute toxicity evaluation

“…[ 5–9 ] Due to azomethine moiety, Schiff bases function as important ligands in the metallic complexes, transforming those into stable structures able to increase the biological effect of the ligand itself through its coordination with metal ions. [ 10–16 ] The design of coordination complexes is guided by the Schiff base ligands and various important transitional metals, such Pd 2+ , Pt 2+ , Cu 2+ , Zn 2+ , Ni 2+ , and Co 2+ . Besides the increased biological effect, the newly obtained structure gains a lipophilic character that facilitates crossing the membrane barrier.…”

Theoretical Study of the Structural Stability, Chemical Reactivity, and Protein Interaction for NMP Compounds as Modulators of the Endocannabinoid System

“…For NMP-4 the presence of methoxy group in the absorption region at 3106.0 and 2976.5 cm −1 for asymmetric and symmetric stretching of CH 3 group, respectively, is closed to the reported region at 2830-2815 cm −1 [15]. The C-O-C stretching is in 1239.0 cm −1 , the reported region for ether group is 1300-1000 cm −1 [16][17][18]. Furthermore, the 585 cm −1 vibration of the O-C-C bending is according to the region 580-505 cm −1 for aromatic compounds with methoxy groups [15].…”

“…The asymmetric and symmetric C-H stretching for the piperidine group are 3039.3 and 2991.0 cm −1 for NMP-4, and 3039.3 and 2989.0 cm −1 for NMP-7. The reported value in literature for asymmetric C-H stretching is 3000-2800 cm −1 and for the symmetric C-H stretching is 2870-2850 cm −1 [15][16][17].…”

Development and structure elucidation of new VO2+, Mn2+, Zn2+, and Pd2+ complexes based on azomethine ferrocenyl ligand: DNA interaction, antimicrobial, antioxidant, anticancer activities, and molecular docking

“…Therefore, the proposed interaction of the FCAPMn complex, for example, with DNA, could be via intercalation or replacement as presented in Scheme 3. [ 49 ]…”