New phthalimide‐appended Schiff bases: Studies of DNA binding, molecular docking and antioxidant activities

Abstract

Herein, we investigated new phthalimide-based Schiff base molecules as promising DNA-binding and free radical scavenging agents. Physicochemical properties of these molecules were demonstrated on the basis of elemental analysis, ultraviolet-visible (UV-Vis), infra-red (IR), H and C nuclear magnetic resonance (NMR) spectroscopy. All spectral data are agreed well with the proposed Schiff base framework. The DNA-binding potential of synthesized compounds were investigated by means of UV-visible, fluorescence, iodide quenching, circular dichroism, viscosity and thermal denaturation studies. The intrinsic binding constants (K ) were calculated from absorption studies were found to be 1.1 × 10 and 1.0 × 10 M for compounds 2a and 2b suggesting that compound 2a binding abilities with DNA were stronger than the compound 2b. Our studies showed that the presented compounds interact with DNA through groove binding. Molecular docking studies were carried out to predict the binding between Ct-DNA and test compounds. Interestingly, in silico predictions were corroborated with in vitro DNA-binding conclusions. Furthermore, the title compounds displayed remarkable antioxidant activity compared with reference standard.

Exploring the binding mode of donepezil with calf thymus DNA using spectroscopic and molecular docking methods

“…Tris–HCl buffer containing different concentrations of NaCl from 0 to 0.5 mol·L −1 were prepared in advance. [ 25 ] The pH of all buffer solutions was 7.4. Emission and excitation wavelengths were set as 393 nm and 270 nm, respectively.…”

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.…”

“…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] .…”

“…[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.…”

Synthesis, characterization and preliminary antimicrobial study of some new phthalimide phenyl hydrazide derivatives

“…The basic goal of medicinal chemistry is to create molecules with less harmful properties that have potential efficacy as therapeutic agents. Phthalimide derivatives are one group of such agents that have a wide range of anti-inflammatory, 1,2 antidiabetic, 3 and antioxidant 4 medical uses. There are many phthalimide derivatives as potential anticancer agents.…”