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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

191 Citations (SciVal)

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.

Original language	English
Pages (from-to)	14267-14271
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	43
Early online date	2 Oct 2018
DOIs	https://doi.org/10.1021/jacs.8b08457
Publication status	Published - 31 Oct 2018

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.8b08457Licence: Other

Cite this

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

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.",

author = "Sedgwick, \{Adam C.\} and Dou, \{Wei Tao\} and Jiao, \{Jin Biao\} and Luling Wu and Williams, \{George T.\} and Jenkins, \{A. Toby A.\} and Bull, \{Steven D.\} and Sessler, \{Jonathan L.\} and He, \{Xiao Peng\} and James, \{Tony D.\}",

year = "2018",

month = oct,

day = "31",

doi = "10.1021/jacs.8b08457",

language = "English",

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journal = "Journal of the American Chemical Society",

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AU - Sedgwick, Adam C.

AU - Dou, Wei Tao

AU - Jiao, Jin Biao

AU - Wu, Luling

AU - Williams, George T.

AU - Jenkins, A. Toby A.

AU - Bull, Steven D.

AU - Sessler, Jonathan L.

AU - He, Xiao Peng

AU - James, Tony D.

PY - 2018/10/31

Y1 - 2018/10/31

N2 - 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.

AB - 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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DO - 10.1021/jacs.8b08457

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JF - Journal of the American Chemical Society

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ER -

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

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

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