A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation

Yanhui Zhang; Hao Teng; Ying Gao; Muhammad Wasim Afzal; Jingye Tian; Xi Chen; Haoyang Tang; Tony D. James; Yuan Guo

doi:10.1016/j.cclet.2020.03.020

A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation

Yanhui Zhang, Hao Teng, Ying Gao, Muhammad Wasim Afzal, Jingye Tian, Xi Chen, Haoyang Tang, Tony D. James, Yuan Guo

Department of Chemistry

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

44 Citations (SciVal)

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Abstract

Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.

Original language	English
Pages (from-to)	2917-2920
Journal	Chinese Chemical Letters
Volume	31
Issue number	11
Early online date	6 Mar 2020
DOIs	https://doi.org/10.1016/j.cclet.2020.03.020
Publication status	Published - 30 Nov 2020

Funding

We gratefully acknowledge the financial support from the National Natural Science Foundation of China (Nos. 21977082 , 21472148 and 21807088 ), Open Funding Project of the State Key Laboratory of Bioreactor Engineering (No. 2018OPEN12 ), Special Foundation of the Education Committee of Shaanxi Province (No. 18JK0702 ), Technology Plan Project of Xi'an (Nos. 201805040YD18CG24 and GXYD18.1 ) and Academic Backbone of Northwest University Outstanding Youth Support Program . Tony D. James wishes to thank the Royal Society for a Wolfson Research Merit Award.

Keywords

2-Pyridylhydrazones
Fluorescent probes
Hypochlorous acid
Reactive oxygen species
Triazolopyridines

ASJC Scopus subject areas

General Chemistry

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10.1016/j.cclet.2020.03.020

Chinese Chemical Letters.PDFAccepted author manuscript, 600 KBLicence: CC BY-NC-ND

Cite this

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title = "A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation",

abstract = "Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.",

keywords = "2-Pyridylhydrazones, Fluorescent probes, Hypochlorous acid, Reactive oxygen species, Triazolopyridines",

author = "Yanhui Zhang and Hao Teng and Ying Gao and Afzal, {Muhammad Wasim} and Jingye Tian and Xi Chen and Haoyang Tang and James, {Tony D.} and Yuan Guo",

year = "2020",

month = nov,

day = "30",

doi = "10.1016/j.cclet.2020.03.020",

language = "English",

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AU - Zhang, Yanhui

AU - Teng, Hao

AU - Gao, Ying

AU - Afzal, Muhammad Wasim

AU - Tian, Jingye

AU - Chen, Xi

AU - Tang, Haoyang

AU - James, Tony D.

AU - Guo, Yuan

PY - 2020/11/30

Y1 - 2020/11/30

N2 - Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.

AB - Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.

KW - 2-Pyridylhydrazones

KW - Fluorescent probes

KW - Hypochlorous acid

KW - Reactive oxygen species

KW - Triazolopyridines

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M3 - Article

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SP - 2917

EP - 2920

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 11

ER -

A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation

Abstract

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Keywords

ASJC Scopus subject areas

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Cite this

A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation

Abstract

Funding

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

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Raman confocal microscope RENISHAM INVIA

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