Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin

Abstract

There is a complex interplay between the structural and other physicochemical properties of new compounds and the molecules in living organisms. To understand the mechanism of the interactions at the molecular level, the correlations between the selected properties and their biological responses have to be examined. With this aim, in this paper, density functional theory (DFT) and LMP2 calculations were carried out for the 2-acetylpyridine-aminoguanidine ligand, L, and its copper(II) complexes containing different monoanionic ligands. In addition, several parameters, most frequently used for the prediction of drug-likeness of new compounds, were calculated. The influence of the compounds on the effectiveness of the reference chemotherapeutic drug cisplatin was determined in vitro, by comparison of their combination indices (CIs). The drug interactions between cisplatin and the earlier synthesized ligands L1 (bis(3-chloropyridazine-6-hydrazone)-2,6-diacetylpyridine) and L2 (bis(phthalazine-1-hydrazone)-2,6-diacetylpyridine) and their Co(III), Ni(II), Cu(II) and Zn(II) complexes, respectively, were also measured. The ligands L, L2, and L3, as well as their complexes, showed different interactions in combination with cisplatin from strong antagonism of L to strong synergism of 4-L1 and 4-L2. The experimental results and the calculated parameters were analyzed to evaluate their correlation with the measured interactions. The thermal stability of the LÁ2HCl ligand and its four copper(II) complexes was determined and the thermal stability data were correlated to selected calculated molecular descriptors.

Molecular Structure, Spectral Investigations, Hydrogen Bonding Interactions and Reactivity-Property Relationship of Caffeine-Citric Acid Cocrystal by Experimental and DFT Approach

“…s.u., 2) the molecular weight within range 180–500 g mol −1 , 3) the number of atoms from 20–70. Further, the MR value is responsible for the lipophilicity, binding property, polarizability and dispersitivity of the molecular system ( Magyari et al, 2018 ). The calculated values of MR for CAF, monomer and dimer model of cocrystal are 30.26 e.…”

Pharmacophoric features for a very potent 5‐spirofluorenehydantoin inhibitor of cancer efflux pump ABCB1, based on X‐ray analysis

“…A checkerboard microplate method was applied to study the effect of drug interactions between the tested compounds and the chemotherapeutic drug, doxorubicin (Teva Pharmaceuticals), thus to determine the combination index (CI) for the compounds (Magyari et al., ).…”

Recent Progress in Metal‐Incorporated Acyclic Schiff‐Base Derivatives: Biological Aspects

“…Numerous Schiff-bases and their derivatives have been reported to possess promising biological properties and several review articles have been published in the past few years. [37][38][39][40][41][42][43][44] Recently, review articles regarding the biological applications of macrocyclic Schiff-base ligands and their metal complexes have been published. [32,34] However, no comprehensive review has been published recently on the biological properties of metallic derivatives of acyclic Schiff-base ligands.…”

“…[34] Macrocyclic Schiff-bases [32][33][34] have found important applications in macrocyclic and supramolecular chemistry, and various heterocyclic Schiff-bases and their derivatives play crucial roles in medicinal chemistry. [35,36] Furthermore, depend-to their structural flexibility, they can be synthetically modified and fine-tuned for specific biological applications and many metallic [3,15,17,18,[37][38][39] and non-metallic [15,[40][41][42][43][44] derivatives of Schiffbases are being researched extensively to develop new compounds with desired biological properties. The imine or azomethine group in structure-activity relationship (SAR) studies of Schiff-bases have shown the considerable chemical and biological importance for the lone pair of electrons in the sp 2 -hybridized orbital of nitrogen atom of the À C=NÀ group.…”

“…Numerous Schiff‐bases and their derivatives have been reported to possess promising biological properties and several review articles have been published in the past few years [37–44] . Recently, review articles regarding the biological applications of macrocyclic Schiff‐base ligands and their metal complexes have been published [32,34] .…”