121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-399
Subject A BODIPY-based Fluorescence Turn-On Probe for Electrochemiluminescent Detection and in Vivo Imaging of Hydrogen Peroxide
Authors Yon Namkoong, JONG-IN HONG*
Department of Chemistry, Seoul National University, Korea
Abstract Hydrogen peroxide (H2O2), produced through various metabolic pathways in biological systems, acts as a signaling molecule in general but becomes a strong oxidant at higher concentration. As one of Reactive Oxygen Species, H2O2 is well known for its cytotoxicity, which causes oxidative stress in cells and results in cellular damages. Despite the renowned importance of H2O2 in bioanalytical chemistry, a few methods have been developed for rapid detection of H2O2 due to its transient nature. Thus, fluorescent probes with fast reaction rates and high sensitivity can be powerful tools for medical diagnosis. Here we report a probe 1 that can detect H2O2 in the right place at the right time. The probe 1 consists of three parts, a fluorophore (BODIPY), a linker (pyridinium), and a reaction site (boronic pinacol ester). Two pyridinium moieties at α-positions of BODIPY enables the probe 1 successfully target mitochondria. In presence of H2O2, the probe 1 exhibits rapid response with bright red fluorescence turn-on. The reaction was saturated within 20 minutes under mild basic conditions. At physiological pH, only half an hour is required to determine H2O2. Moreover, electrochemiluminescence (ECL) of the probe 1 is anticipated because the BODIPY core is substituted with alkyl groups, minimizing instability during the ECL process. The basic condition induced by the coreactant TPrA provides a good environment for the probe 1. In short, the probe 1 is a promising chemodosimeter able to monitor H2O2 with fast response and high sensibility both in mitochondria and by ECL analysis.
E-mail yonnk@snu.ac.kr