An ESIPT probe for the ratiometric imaging of peroxynitrite facilitated by binding to Aβ-aggregates

Sedgwick, Adam C., Dou, Wei-Tao, Jiao, Jin-Biao, Wu, Luling, Williams, George, Jenkins, A. Toby A., Bull, Steven D., Sessler, Jonathan L., He, Xiao-Peng and James, Tony D. (2018) An ESIPT probe for the ratiometric imaging of peroxynitrite facilitated by binding to Aβ-aggregates. Journal of the American Chemical Society, 140 (43), 14267–14271. (doi:10.1021/jacs.8b08457).

Abstract

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-β (Aβ) in the presence of ONOO–. The 3-HF-OMe probe was found to produce a ratiometric response toward ONOO– when bound to Aβ 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.

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Contributors

Author: George Williams

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