Aminocoumaranones as Chemiluminescence Indicators of the Urease Activity and Hydrogen Peroxide

Abstract

Objective: The phenomenon of chemiluminescence - the emission of light by a substance after oxidation - has been known for a very long time. Substances capable of chemiluminescence are actively used for the detection and quantitative determination of a wide variety of analytes. In this work, we studied the possibility of using 3-amino-coumaranones for the detection of hydrogen peroxide and urease activity study. Methods: In this work, we synthesized a series of 3-amino-coumaran-2-one derivatives, which can be divided into two groups: amide derivatives and urea derivatives. The optical and chemiluminescent properties of all the obtained compounds were studied under various conditions. Results and Discussion: In this work, a series of 3-amino-coumaranones was synthesized. It has been found that amide derivatives and derivatives of asymmetrically substituted ureas have significant chemiluminescence under various conditions. The introduction of the electron-donor groups in the coumaranone moiety and increasing of the conjugated π-system of coumaranones allow to shift 30–40 nm of the chemiluminescence maxima to the long-wavelength region. For N,N-disubstituted unsymmetrical urea derivatives it is shown that the luminescence intensity can be different under various conditions. It has been shown that derivatives of N,N-disubstituted unsymmetrical ureas can be used for the determination of hydrogen peroxide, and some compounds, due to their bright luminescence in the presence of urease, can be used as indicators of its enzymatic activity. Conclusions: We showed that some 3-amino-coumaranones can be used for detecting the urease and hydrogen peroxide.