Synthesis, Computational and cytotoxicity studies of aryl hydrazones of β-diketones: Selective Ni2+ metal Responsive fluorescent chemosensors

Abstract

A new fluorescent sensor 2-(2-(3-chloro-4-fluorophenyl)hydrazono)-5,5-dimethyl cyclohexane-1,3-dione (A) and 2-(2-(4-chloro-2-nitrophenyl)hydrazono)-5,5-dimethyl cyclohexane-1,3-dione (B) composed of a β-diketones of aryl hydrazones synthesized by simple and cost-effective method. Various analytical tools analyzed the structural investigations of the synthesized substituted β-diketones of aryl hydrazones like FT-IR, ¹H, ¹³C NMR and UV-Vis techniques, Single-crystal X-ray diffraction studies (SCXRD) (for A), Scanning electron microscopy (SEM), and fluorescence spectroscopy. SEM also investigates surface morphology modifications of aryl hydrazones and Ni²⁺ complex. Furthermore, the metal sensing (Chemo sensing) behavior of newly prepared aryl hydrazones of β-diketones derivatives was further studied by fluorescence spectroscopy. The aryl hydrazones sensor materials show admirable fluorescence selectivity with enrichment to Ni²⁺ over different cations in an aqueous ethanol solution with a recognition extremity of 4 μM-7 μM. A joint experimental and theoretical investigation was led on the chemical structure employing a density functional theory (DFT) (B3LYP), engaging a 6-31G basis set. The DFT technique's enhanced geometrical bond angles and lengths exhibited great covenant with the experimental results. The highest occupied molecular (HOMO) orbital and lowest unoccupied (LUMO) molecular orbital energy has been concluded. The cytotoxicity studies show these compounds impede the growth of KB cells highly and from the studies to evaluate their capability to accurately dock aryl hydrazones to antibodies of cancer protein such as 4LRH, 4L9K, 4 EKD and 4GIW cancer proteins.

Keywords: Aryl hydrazones of β-diketones; Cytotoxicity; DFT method; Molecular docking; Ni(2+) chemosensor.