A novel 2-aminophenalenone-based fluorescent probe designed for monitoring H2O2 for in vitro and in vivo bioimaging

• Published in: Talanta (Oxford) 2024-05, Vol.271, p.125669-125669, Article 125669
• Main Authors: Saygili, Ecem, Ersoz-Gulseven, Esra, Kıbrıs, Erman, Cakan-Akdogan, Gulcin, Ucuncu, Muhammed
• Format: Article
• Language: English
• Subjects: Aminophenalenone; Fluorescent probes; Hydrogen peroxide; Intracellular; Zebrafish
• ISSN: 0039-9140; 1873-3573
• DOI: 10.1016/j.talanta.2024.125669

A significant compound in living organisms, hydrogen peroxide (H2O2) plays a dual role as a signalling molecule in cellular communication and as a pivotal biomarker in assessing disease and oxidative stress. Thus, the detection of abnormal changes in H2O2 levels is essential to understanding its function and involvement in biological systems. The growing demand to meet the specific needs for applications, particularly in biological systems, has sharpened focus on highly sensitive, highly selective molecular sensors and, in turn, heightened interest in these diagnostic tools with innovative designs. In our study, 2-aminophenalenone (2-AP) was used for the first time as a fluorophore in a fluorescent probe. The 2-APB molecule obtained from the reaction of 2-AP with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzyl chloroformate exhibited a highly selective and sensitive (i.e. 62 nM) detection profile for H2O2 compared with the other reactive oxygen species, anions, and metal cations. Moreover, offering naked-eye detection in aqueous solutions, 2-APB demonstrated excellent sensing performance, detection and real-time monitoring in relation to exogenous H2O2 in cells and endogenous H2O2 in zebrafish embryos. [Display omitted] •The use of 2-aminophenalenone (2-AP) as a fluorophore was demonstrated for the first time.•The naked eye and fluorometric detection of H2O2 with 2-APB was demonstrated.•The high sensitivity of 2-APB to H2O2 was demonstrated (LOD = 62 nM).•The high selectivity of 2-APB to H2O2 over the other reactive oxygen species (ROS), anions and metal cations was demonstrated.•The usability of 2-APB for both in vitro and in vivo bioimaging was proven.