Aniline-co-o-anthranilic Acid Copolymer-Chitosan/Ag@AgCl Nanohybrid as a Carrier for (E)-N′-(Pyridin-2-ylmethylene) Hydrazinecarbothiohydrazide Release and Antimicrobial Activity

Abstract

Poly(aniline-co-o-anthranilic acid)-chitosan/silver@silver chloride (PAAN-CS/Ag@AgCl) nanohybrids were synthesized using different ratios of Ag@AgCl through a facile one-step process. The presence of CS led to the formation of the nanohybrid structure and prevented the aggregation of the copolymer efficiently. The synthesized nanohybrids were fully characterized by transmission electron microscopy, X-ray diffraction, Fourier transform infrared (FTIR) spectroscopy, and thermogravimetric analysis. (E)-N′-(Pyridin-2-ylmethylene) hydrazinecarbothiohydrazide I was prepared using thiosemicarbazide and confirmed by 1H-NMR, 13C-NMR, and FTIR analyses. Loading of the azine derivative I using various concentrations at different pH values onto the nanohybrid was followed by UV–vis spectroscopy. Langmuir and Freundlich adsorption isotherm models were used to describe the equilibrium isotherm, and the adsorption followed the Langmuir adsorption isotherm. A pseudo-second-order model was used to describe the kinetic data. A PAAN-CS/Ag@AgCl nanohybrid loaded with azine I interestingly showed efficient antimicrobial activity against Escherichia coli and Staphylococcus aureus more than the azine derivative I. The release of azine I at different pH values (2–7.4) was investigated and the kinetics of release were studied using zero-order, first-order, second-order, Higuchi, Hixson–Crowell, and Korsmeyer–Peppas equations.