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

Adam C Sedgwick; Wei-Tao Dou; Jin-Biao Jiao; Luling Wu; George T Williams; A Toby A Jenkins; Steven D Bull; Jonathan L Sessler; Xiao-Peng He; Tony D James

doi:10.1021/jacs.8b08457

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

J Am Chem Soc. 2018 Oct 31;140(43):14267-14271. doi: 10.1021/jacs.8b08457. Epub 2018 Oct 16.

Authors

Affiliations

¹ Department of Chemistry , University of Bath , Bath BA2 7AY , U.K.
² Department of Chemistry . University of Texas at Austin , 105 East 24th Street A5300 , Austin , Texas 78712-1224 , United States.
³ Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering , East China University of Science and Technology , 130 Meilong Rd. , Shanghai 200237 , China.
⁴ Department of Materials and Life Sciences, Faculty of Science and Technology , Sophia University , 7-1 Kioi-cho , Chiyoda-ku, Tokyo 102-8554 , Japan.

PMID: 30277762
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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amyloid beta-Peptides / chemistry*
Animals
Flavonoids / chemical synthesis
Flavonoids / chemistry*
Fluorescent Dyes / chemical synthesis
Fluorescent Dyes / chemistry*
Mice
Mice, Transgenic
Molecular Structure
Optical Imaging*
Peroxynitrous Acid / analysis*
Protein Aggregates
Protons*

Substances

Amyloid beta-Peptides
Flavonoids
Fluorescent Dyes
Protein Aggregates
Protons
Peroxynitrous Acid
3-hydroxyflavone