Supramolecular Interaction of Gliclazide with Cucurbit[7]uril and its Analytical Application

Abstract

Gliclazide (GLZ) is non-fluorescent in aqueous solution. This property makes its determination through direct fluorescent methods impossible. Palmatine (PAL) exhibits very weak fluorescence emissions in aqueous solution. However, in acidic media at room temperature, PAL can react with cucurbit[7]uril (CB[7]) to form a stable complex and the fluorescence intensity of the complex is greatly enhanced. Dramatic quenching of the fluorescence intensity of the CB[7]–PAL complex was observed with the addition of GLZ. The competing reactions and the supramolecular interaction mechanisms between GLZ and PAL as they fight for occupancy of the CB[7] cavity were studied using spectrofluorimetry, 1H NMR spectroscopy, and molecular modelling calculations. The association constants of the complexes formed between the host and the guest were determined. Based on the significant quenching of the supramolecular complex fluorescence intensity, a fluorescent probe method of high sensitivity was developed to determine GLZ in its pharmaceutical dosage forms and in human plasma with good precision and accuracy. The linear range of the method was from 0.003 to 2.100 μg mL–1. The limit of detection was 0.001 μg mL–1. This shows that the proposed method has promising potential for therapeutic monitoring and pharmacokinetics and for clinical application.