Two-photon ESIPT-based fluorescent probe using 4-hydroxyisoindoline-1,3-dione for the detection of peroxynitrite

Luling Wu; Xue Tian; Dong Joon Lee; Juyoung Yoon; Chang Su Lim; Hwan Myung Kim; Tony D. James

doi:10.1039/d1cc03160k

Two-photon ESIPT-based fluorescent probe using 4-hydroxyisoindoline-1,3-dione for the detection of peroxynitrite

Luling Wu, Xue Tian, Dong Joon Lee, Juyoung Yoon, Chang Su Lim, Hwan Myung Kim, Tony D. James

Department of Chemistry & Nanoscience

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

49 Scopus citations

Abstract

Excited-state intramolecular proton transfer (ESIPT)-based fluorophores with two-photon excitation fluorescence (TPEF) are rare. Our aim with this research was to develop ESIPT-based fluorophores exhibiting TPEF. Herein, we used 4-hydroxyisoindoline-1,3-dione as a scaffold to develop a two-photon fluorescent probe BHID-Bpin, for the detection of peroxynitrite (ONOO-). BHID-Bpin exhibits excellent selectivity, sensitivity, and fast response towards ONOO- in PBS buffer solution (10 mM, pH = 7.40). Additionally, BHID-Bpin displays high photo-stability under two-photon irradiation at 750 nm. Furthermore, the probe can image endogenous ONOO- in HeLa cells and exogenous ONOO- in rat hippocampal slices at a depth of 110 μm.

Original language	English
Pages (from-to)	11084-11087
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	84
DOIs	https://doi.org/10.1039/d1cc03160k
State	Published - 28 Oct 2021

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© The Royal Society of Chemistry.

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title = "Two-photon ESIPT-based fluorescent probe using 4-hydroxyisoindoline-1,3-dione for the detection of peroxynitrite",

abstract = "Excited-state intramolecular proton transfer (ESIPT)-based fluorophores with two-photon excitation fluorescence (TPEF) are rare. Our aim with this research was to develop ESIPT-based fluorophores exhibiting TPEF. Herein, we used 4-hydroxyisoindoline-1,3-dione as a scaffold to develop a two-photon fluorescent probe BHID-Bpin, for the detection of peroxynitrite (ONOO-). BHID-Bpin exhibits excellent selectivity, sensitivity, and fast response towards ONOO- in PBS buffer solution (10 mM, pH = 7.40). Additionally, BHID-Bpin displays high photo-stability under two-photon irradiation at 750 nm. Furthermore, the probe can image endogenous ONOO- in HeLa cells and exogenous ONOO- in rat hippocampal slices at a depth of 110 μm.",

author = "Luling Wu and Xue Tian and Lee, \{Dong Joon\} and Juyoung Yoon and Lim, \{Chang Su\} and Kim, \{Hwan Myung\} and James, \{Tony D.\}",

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year = "2021",

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doi = "10.1039/d1cc03160k",

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T1 - Two-photon ESIPT-based fluorescent probe using 4-hydroxyisoindoline-1,3-dione for the detection of peroxynitrite

AU - Wu, Luling

AU - Tian, Xue

AU - Lee, Dong Joon

AU - Yoon, Juyoung

AU - Lim, Chang Su

AU - Kim, Hwan Myung

AU - James, Tony D.

PY - 2021/10/28

Y1 - 2021/10/28

N2 - Excited-state intramolecular proton transfer (ESIPT)-based fluorophores with two-photon excitation fluorescence (TPEF) are rare. Our aim with this research was to develop ESIPT-based fluorophores exhibiting TPEF. Herein, we used 4-hydroxyisoindoline-1,3-dione as a scaffold to develop a two-photon fluorescent probe BHID-Bpin, for the detection of peroxynitrite (ONOO-). BHID-Bpin exhibits excellent selectivity, sensitivity, and fast response towards ONOO- in PBS buffer solution (10 mM, pH = 7.40). Additionally, BHID-Bpin displays high photo-stability under two-photon irradiation at 750 nm. Furthermore, the probe can image endogenous ONOO- in HeLa cells and exogenous ONOO- in rat hippocampal slices at a depth of 110 μm.

AB - Excited-state intramolecular proton transfer (ESIPT)-based fluorophores with two-photon excitation fluorescence (TPEF) are rare. Our aim with this research was to develop ESIPT-based fluorophores exhibiting TPEF. Herein, we used 4-hydroxyisoindoline-1,3-dione as a scaffold to develop a two-photon fluorescent probe BHID-Bpin, for the detection of peroxynitrite (ONOO-). BHID-Bpin exhibits excellent selectivity, sensitivity, and fast response towards ONOO- in PBS buffer solution (10 mM, pH = 7.40). Additionally, BHID-Bpin displays high photo-stability under two-photon irradiation at 750 nm. Furthermore, the probe can image endogenous ONOO- in HeLa cells and exogenous ONOO- in rat hippocampal slices at a depth of 110 μm.

UR - https://www.scopus.com/pages/publications/85118196794

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DO - 10.1039/d1cc03160k

M3 - Article

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VL - 57

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JO - Chemical Communications

JF - Chemical Communications

IS - 84

ER -

Two-photon ESIPT-based fluorescent probe using 4-hydroxyisoindoline-1,3-dione for the detection of peroxynitrite

Abstract

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