An ESIPT Probe for the Ratiometric Imaging of Peroxynitrite Facilitated by Binding to A beta-Aggregates

作者:Sedgwick, Adam C.; Dou, Wei-Tao; Jiao, Jin-Biao; Wu, Luling; Williams, George T.; Jenkins, A. Toby A.; Bull, Steven D.; Sessler, Jonathan L.*; He, Xiao-Peng*; James, Tony D.*
来源:Journal of the American Chemical Society, 2018, 140(43): 14267-14271.
DOI:10.1021/jacs.8b08457

摘要

A series of 3-hydroxyflavone (3-HF) ESIPT (excited-state intramolecular proton transfer) boronate-based fluorescent probes have been developed for the detection of peroxynitrite (ONOO-). The dyes are environmentally sensitive, and each probe exhibited a ratiometric response toward ONOO- in a micellar environment. The probes were used to image different aggregation states of amyloid-beta (A beta) in the presence of ONOO-. The 3-HF-OMe probe was found to produce a ratiometric response toward ONOO- when bound to A beta aggregates, resulting in a novel host-guest ensemble, which adds insight into the development of other ESIPT-based probes for the simultaneous sensing of fibrous proteins/peptides and environmental ROS/RNS.