Back to Search Start Over

Biological evaluation, proposed molecular mechanism through docking and molecular dynamic simulation of derivatives of chitosan

Authors :
Rahime Eshaghi Malekshah
Farideh Shakeri
Ali Khaleghian
Maral Hemati
Mohammadreza Aallaei
Source :
International journal of biological macromolecules. 166
Publication Year :
2020

Abstract

We synthesized Schiff base and its complexes derivatives of chitosan (CS) in order to develop antibiotic compounds based on functionalized-chitosan against gram-positive and gram-negative bacteria. IR, UV-Vis, AFM, SEM, Melting point, X-ray diffraction (XRD), elemental analysis, and 1H NMR techniques were employed to characterize the chemical structures and properties of these compounds. XRD, UV-Vis, and 1H NMR techniques confirmed the formation of Schiff base and its functionalized-chitosan to metals. Subsequently, our antibacterial studies revealed that antibacterial activities of [Zn(Schiff base)(CS)] against S. aureus bacteria increased compared to those of their compounds. In addition, hemolysis test of CS-Schiff base-Cu(II) demonstrated better hemolytic activity than vitamin C, CS-Schiff base, CS-Schiff base-Zn(II), and CS-Schiff base-Ni(II). In a computational strategy, we carried out the optimization of compounds with molecular mechanics (MM+), Semi-emprical (AM1), Abinitio (STO-3G), AMBER, BIO+(CHARMM), and OPLS. Frontier orbital density distributions (HOMO and LUMO), and the optimized computational UV of the compounds were assessed. The optimized computational UV-Vis was similar to the experimental UV-Vis. We applied the docking methods to predict the DNA binding affinity, Staphylococcus aureus enoyl-acyl carrier protein reductase (ENRs), and Staphylococcus aureus enoyl-acyl carrier protein reductase (saFabI). Ultimately, the obtained data herein suggested that Schiff base is more selective toward ENRs and saFabI compared to chitosan, its complexes, and metronidazole.

Details

ISSN :
18790003
Volume :
166
Database :
OpenAIRE
Journal :
International journal of biological macromolecules
Accession number :
edsair.doi.dedup.....443e726cb054f5bfb012af2b346a6099