Issue 9, 2018

A chemiluminescent probe for cellular peroxynitrite using a self-immolative oxidative decarbonylation reaction

Abstract

Peroxynitrite (ONOO) is a highly reactive oxygen species which has been recognized as an endogenous mediator of physiological activities like the immune response as well as a damaging agent of oxidative stress under pathological conditions. While its biological importance is becoming clearer, many of the details of its production and mechanism of action remain elusive due to the lack of available selective and sensitive detection methods. Herein, we report the development, characterization, and biological applications of a reaction-based chemiluminescent probe for ONOO detection, termed as PNCL. PNCL reacts with ONOOvia an isatin moiety through an oxidative decarbonylation reaction to initiate light emission that can be observed instantly with high selectivity against other reactive sulphur, oxygen, and nitrogen species. Detailed studies were performed to study the reaction between isatin and ONOO, which confirm selectivity for ONOO over NO2˙. PNCL has been applied for ONOO detection in aqueous solution and live cells. Moreover, PNCL can be employed to detect cellular ONOO generated in macrophages stimulated to mount an immune response with lipopolysaccharide (LPS). The sensitivity granted by chemiluminescent detection together with the specificity of the oxidative decarbonylation reaction provides a useful tool to explore ONOO chemistry and biology.

Graphical abstract: A chemiluminescent probe for cellular peroxynitrite using a self-immolative oxidative decarbonylation reaction

Supplementary files

Article information

Article type
Edge Article
Submitted
28 Nov 2017
Accepted
31 Jan 2018
First published
31 Jan 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 2552-2558

A chemiluminescent probe for cellular peroxynitrite using a self-immolative oxidative decarbonylation reaction

J. Cao, W. An, A. G. Reeves and A. R. Lippert, Chem. Sci., 2018, 9, 2552 DOI: 10.1039/C7SC05087A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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