Synthesis, DNA Binding, and Molecular Docking Studies of Dimethylaminobenzaldehyde-Based Bioactive Schiff Bases

Zainab M Almarhoon,Wedad A Al-Onazi,Asma A Alothman,Amal M Al-Mohaimeed,Eida S Al-Farraj

doi:10.1155/2019/8152721

Abstract

A new series of p-dimethylaminobenzaldehyde derivatives were tested for therapeutic potential by exploring their properties through characterization. The derivatives were synthesized by 1 : 1 condensation reaction of p-dimethylaminobenzaldehyde and substituted amines. The synthesized compounds 1–8 were characterized by different characterization techniques including IR, mass, 1H NMR, and 13C NMR spectroscopy, elemental analysis, and mass spectrometry. Furthermore, binding of these Schiff bases to Ct-DNA was examined by absorption spectroscopy, fluorescence quenching, circular dichroic, viscosity measurement, molecular docking, and molecular dynamics simulation methods. Schiff bases were tested for antimicrobial activity against bacterial species Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Staphylococcus aureus by the disc diffusion method. The pharmacological treatment of Schiff bases showed that 1–8 have promising potential against tested bacterial strains. The molecular docking study of the target compounds was also carried out against B-DNA dodecamer d(CGCGAATTCGCG)2, and it has been found that 1–8 can bind to Ct-DNA via an intercalative mode. DPPH free radical and hydrogen peroxide scavenging assays were employed to assess the antioxidant potential of synthesized Schiff bases.

Highlights

Heterocyclic Schiff base chemistry is one of the attractive and challenging fields in current medical science
Heterocyclic Schiff base derivatives are the most extensively used organic compounds with broad range of applications used as pigments, dyes, catalysts, and intermediates in many organic reactions [1, 2]. ey showed phototropism and thermochromism in the solid state used in optical and electrochemical sensors for the detection and enhancement of selectivity and sensitivity [3, 4]
Due to their applications in biological, analytical, and medicinal field, and their role as catalysts in organic synthesis, heterocyclic Schiff bases are considered as one of the most potential groups of heterocyclic compounds [5]. e presence of azomethine group in heterocyclic Schiff base derivatives makes it very critical for various biological applications such as antifungal [6, 7], antibacterial [8, 9], antiproliferative [10], anticoagulant [11], anti-inflammatory [12], and antiviral [13] agents. ey have been widely used in coordination chemistry mainly due to their facile synthesis, electronic properties, and good solubility in common solvents [14]

Summary

Introduction

Heterocyclic Schiff base chemistry is one of the attractive and challenging fields in current medical science. Ey have been used extensively in biochemistry, material science, hydrometallurgy, catalysis and separation phenomena, and many of the biological processes [15, 16] Due to their thermal stability, Journal of Chemistry biological applications, and presence of nitrogen atom in aromatic ring, pyridine and pyrimidine-based heterocyclic compounds are considered to be better ligands [17]. Researchers have been working for last many years to find new antibacterial agents due to the development of bacterial resistance [28] In this regard, we have tried to develop such types of heterocyclic derivatives which can bind with DNA and significant antioxidant to prevent damage caused by free radicals [29]; we reported synthesis of unknown pdimethylaminobenzaldehyde derivatives 1–8 and screened their DNA binding, fluorescence quenching, and antioxidant and antimicrobial assays. In this work, we calculated some molecular docking parameters of compounds in order to correlate them with their antimicrobial activity

Experimental Section

Results and Discussion

DNA Binding Studies

Antioxidant Assay