Design of a dual functionalized chemiluminescence ultrasensitive probe for quinones based on their redox cycle. Application to the determination of doxorubicin in lyophilized powder and human serum

Abstract Quinones are ubiquitous compounds that have two-sided nature; a beneficial one, especially in the electron transport chain, and a toxic one through the generation of reactive oxygen species in vivo. Herein we developed a new dual-function chemiluminescence probe for their determination namely N-(4-aminobutyl)-N-ethylisoluminol-lipoic acid (ABEI-LA). This probe has two moieties, a reductant one, lipoic acid (LA), which upon its redox cycle reaction with quinones, generate superoxide anion, and the other moiety is the luminophore, ABEI, which generates intense chemiluminescence upon reaction with the generated superoxide anion. ABEI-LA is the first single reagent that could generate CL with quinones in a one-step operation. A simple rapid chemiluminescence assay for the anticancer drug, doxorubicin, was developed using ABEI-LA as a probe. The method showed good linearity towards doxorubicin in the range of 1-200 nM and excellent sensitivity with a detection limit of 0.17 nM (25 pg/assay). The proposed probe, ABEI-LA, was successfully applied for the quantification of doxorubicin, in lyophilized powder for injections and human serum samples and it showed very good recoveries of 84-91% and 98-101%, respectively. These results demonstrate the ability of ABEI-LA for the determination of quinones in different matrices enabling the in-depth study of quinones two-sided nature.