120th General Meeting of the KCS

Type Poster Presentation
Area Medicinal Chemistry
Room No. Exhibition Hall 2+3
Time 10월 19일 (목요일) 11:00~12:30
Code MEDI.P-343
Subject New Reduced Asymmetric Xanthene Fluorescent Probes with Improved Chemical Stability and Reactivity: Application to Detection of Nitroreductase
Authors Tae-Hwan Lim, KUNAL MORE, Dong-Jo Chang*
Department of Pharmacy, Suncheon National University, Korea
Abstract Xanthene fluorophores including fluorescein, rhodamine and their hybrid structure, rhodol, are among the most commonly used fluorescent probes, and many activity-based fluorescent probes have been discovered with their asymmetric derivatives in many areas including biology and medicines. Rhodol and rhodamine derivatives have been of great interest as activity-based fluorescent probes that can detect various phenonmena in live cells because they are fluorescent with a high quantum yield within broad ranges of pH and are also known to be photo-stable as compared to other fluorescent probes such as fluorescein. However, as with other xanthene fluorophores, rhodol and rhodamine probes also have a synthetic disadvantage that it’s difficult to modify and introduce various substituents at the terminal of xanthene ring due to low chemical stability to acids and bases. A few reduced xanthene fluorophores including fluorescein and rhodol have been developed, but the reduced asymmetric rhodamine fluorescent probe has not been discovered. Herein, we designed, synthesized and evaluated the reduced asymmetric xanthene fluorophores including fluorescein, rhodol and rhodamine moieties. In order to confirm synthetic advantage of reduced xanthene fluorophores, we evaluated chemical stability of reduced symmetric and asymmetric fluorophores by reacting them under alkylation and amide coupling reaction conditions. Additionally, we performed the study for evaluation of fluorogenic nature of reduced fluorophores. Nitroreductase (NTR)-, which is a representative biomarker of hypoxia, response fluorescent probes were synthesized with these reduced fluorophores, and their fluorescent activities were evaluated in presence of NTR.
E-mail djchang@sunchon.ac.kr