Synthesis, chromism, antimicrobial activity, molecular docking, and pharmacokinetics of novel molecular switchable hydrazones

A series of novel tricyanofuran-hydrazone chromophores were synthesized and characterized by different spectroscopic techniques. The prepared hydrazones displayed solvatochromic activity in different organic solvents. The tricyanofuran-hydrazone was imprinted onto a paper strip as an optical solid-state sensor for aqueous and gaseous ammonia. Due to their reversible halochromism-driven molecular switching, the hydrazone dyes showed variable sensitivity towards different concentrations of aqueous ammonia. The strong electron-withdrawing tricyanofuran fragment promotes a proton transfer from the hydrazone moiety to ammonia, which allows for the recognition of ammonia vapor. The resulting paper sensor demonstrated a reversible sensitivity to ammonia vapor. Using the minimum inhibitory concentration (MIC) method, the dinitro-substituted chromophore showed the strongest antibacterial activity. It was effective against A. fumigatus , C. albicans , E. coli , S. pneumoniae , and S. aureus , with MIC values of <226, <198, <122, <71, and <38, respectively. Thus, the dinitro-substituted chromophore appears to be a promising antibacterial agent. The theoretical molecular docking study of the produced series against a protein of interest (PDB: 1lnz) was performed to assign the binding and type of interaction between ligand and protein amino acids. The pharmacokinetic properties of potential drug candidates for the synthesized chromophores were simulated to determine their efficacy and safety profiles.