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 ONOO-via 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.
Highlights
Peroxynitrite (ONOOÀ) is a highly reactive oxygen species that can be formed biologically from a diffusion-controlled reaction between superoxide (O2cÀ) and nitric oxide (NOc).[1]
As part of a program to develop chemical probes for imaging reactive sulphur,[29,37] oxygen,[30,38,39] and nitrogen species, our laboratory has previously reported that isatin reacts with ONOOÀ via an oxidative decarbonylation reaction to generate anthranilic acid.40 19F NMR probes, 5- uoroisatin and 6- uorisatin, have been developed for selective detection of ONOOÀ
Given the destructive reactivity of hydroxyl radical (HOc), we examined the interference of this species by treating PNCL with ONOOÀ in the presence of the HOc-generating Fenton system (Fig. S4†), where only a minimal reduction in signal was observed
Summary
Peroxynitrite (ONOOÀ) is a highly reactive oxygen species that can be formed biologically from a diffusion-controlled reaction between superoxide (O2cÀ) and nitric oxide (NOc).[1]. We report the development, characterization, and biological applications of a reaction-based chemiluminescent probe for ONOOÀ detection, termed as PNCL.
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