Synthesis, DFT analysis, dyeing potential and evaluation of antibacterial activities of azo dye derivatives combined with in-silico molecular docking and ADMET predictions

Abstract

In the present work eight azo dye derivatives were synthesized using condensation of 1-naphthol, resorcinol and phenol with the p-ntroaniline, o-toluidine, p-chloroniline, among these four of the derivatives are new and their structures were characterized using UV-Vis, 1H, 13C, and DEPT-135 NMR. The dyes were screened for their in vitro antibacterial activities against both Gram-positive and Gram-negative bacterial species at 50, 75, and 100 mg/mL concentration, penicillin as standard drug. Most of the synthesized dyes were showed promising activities against these tested bacterial. Further, the dyeing actions of their fastness and color strength properties were evaluated in terms of dye exhaustion and fixation on cotton, wool, silk, and polyester using the cold and hot dyeing conditions. Comparing the hot better exhaustion and fixation recorded values of dyes action on the four types of fibers shown in cold dyeing condition. They showed good fastness resistance to washing. Molecular docking of synthesized compounds was done using Autodock vina version 4.2 software. Among the investigated ligands dye compounds 1 and 2 exhibited better docking efficiency with DNA gyrase with binding affinity-7.4kcal/mol.