A Highly Efficient and Selective Glycine Based Schiff Base Fluorescent Probe for Dual Sensing of Zn(II) and Cu(II) and its Antibacterial Activity and BSA Interaction Studies

Abstract

A mesogenic glycine based Schiff base compound of the type, (E)‐methyl 2‐((2‐hydroxy‐4‐(tetradecyloxy)benzylidene)amino)acetate (HL) has been successfully synthesized and characterized using analytical and spectroscopic techniques. The Schiff base compound was evaluated for chemosensor activity towards different metal ions using fluorescence spectroscopy. The experiment reveals highly efficient and selective “turn‐on” and “turn‐off” responses of the fluorescence intensity towards zinc(II) and copper(II), respectively, in presence of other metal ions. The binding constant and the stoichiometry ratio were determined using Benesi‐Hildebrand equation giving 1 : 1 stoichiometry. The limits of detection for both the metal ions were estimated from the fluorescence titration experiments. The reversibility nature of the Schiff base probe was also studied using EDTA as chelating ligand. The compound, HL exhibits two INHIBIT logic gates with chemical inputs (i) Zn2+ (IN1) and Cu2+ (IN2) and (ii) Zn2+ (IN1) and EDTA (IN2). An IMPLICATION logic gate was also obtained when Cu2+ (IN1) and EDTA (IN2) serve as chemical inputs. The compound was found to exhibit potent antibacterial activity and efficient binding interaction with BSA. Molecular docking studies were carried out in order to ascertain the degree of interaction and the nature of binding of the compound with the proteins.