Peroxynitrite (ONOO-), owing to its high oxidative and nitrating stress, is associated with several physiological processes in addition to various pathological processes, including those related to neurodegenerative diseases and cancer. Detection of ONOO- at the cellular level is of great significance to understand its pathogenesis. To this end, a variety of fluorescent probes based on small molecules and nanoparticles (NPs) have been engineered and applied as excellent tools for imaging of ONOO- in cells as well as in their diverse biological applications. In this review, we highlight representative cases of fluorescent probes based on recognition mechanism and emphasize their response type (ratiometric, two-photon, long-wavelength/near-infrared, and targeting) in ONOO- detection in the last five years. We further discuss their design strategy, sensing mechanism, and application in bio-imaging and describe NP-based probes according to diverse nanoplatforms.

Recent advances in fluorescent probes of peroxynitrite: Structural, strategies and biological applications

Mercury ion (Hg2+) has been considered as a hazardous heavy metal pollution in water, thus the development of a material for the sensitive detection and efficient adsorption of Hg2+ ions is significant. Herein, a novel coumarin-dithioacetal fluorophore named CA-S was synthesized, and then successfully coated on the chitosan nonwoven fabric. This functionalized fabric exhibited sensitive sensing and efficient adsorption toward Hg2+ ions. The fluorescence response mechanism of the functionalized fiber toward Hg2+ ions was confirmed by experiment and calculation. The detection limit of the functionalized fabric toward Hg2+ ions was 1.26 × 10−7 M. Moreover, this fabric showed favor adsorption capacity (over 1000 mg/g) and adsorption efficiency (within 10 min) toward Hg2+ ions. Meanwhile, this fabric was able to remove almost 99 % Hg2+ ions in real industrial water samples that satisfied the wastewater discharge standard.

A smart chitosan nonwoven fabric coated with coumarin-based fluorophore for selective detection and efficient adsorption of mercury (II) in water

Peroxynitrite (ONOO−), a highly reactive oxygen species (ROS), is implicated with many physiological and pathological processes including cancer, neurodegenerative diseases and inflammation. In this regard, developing effective tools for highly selective tracking of ONOO− is urgently needed. Herein, we constructed a concise and specific fluorescent probe NA-ONOO for sensing ONOO− by conjugating an ONOO−-specific recognition group ((4-methoxyphenylthio)carbonyl, a thiocarbonate derivative) with a naphthalene fluorophore. The probe, NA-ONOO, was in a dark state because the high electrophilicity of (4-methoxyphenylthio)carbonyl disturbs the intramolecular charge transfer (ICT) in the fluorophore. Upon treatment with ONOO−, the fluorescent emission was sharply boosted (quantum yield Φ: 3% to 56.6%) owing to an ONOO− triggered release of (4-methoxyphenylthio)carbonyl from NA-ONOO. Optical analyses showed that NA-ONOO presented high selectivity and sensitivity toward ONOO−. With good cell permeability and biocompatibility, the NA-ONOO probe was successfully applied to imaging and tracing exogenous and endogenous ONOO− in living cells and zebrafish. The probe NA-ONOO presents a new recognition group and a promising method for further investigating ONOO− in living systems.

A thiocarbonate-caged fluorescent probe for specific visualization of peroxynitrite in living cells and zebrafish.

Enhancing probe’s sensitivity for peroxynitrite through alkoxy modification of dicyanovinylchromene

Peroxynitrite (ONOO−) is a highly reactive and short-lived oxidant with low content in cells, and plays an important role in biology. Accordingly, developing a rapid, sensitive, and effective detection approach of cellular ONOO− is very meaningful to further study its biological functions. In this work, a new biosensor BQ for the recognition of ONOO− was facilely synthesized by condensation of 2-hydrazinoquinoline and formylated benzothiazole possessing ‘‘ESIPT + AIE” feature. The probe can be used in a wide range of pH value, and displayed a rapid fluorescence “turn on” response toward ONOO− with low detection limit (5.1 nM) and high selectivity over other competitive substances through ONOO−-triggered oxidative cleavage of C=N double bond. The sensing mechanism of BQ towards ONOO− was proved by 1HNMR and HRMS analysis. Furthermore, the capacity of BQ to detect intracellular ONOO− has been well-demonstrated by fluorescence microscopic imaging experiments, indicating its potential application for investigating the physiological function of ONOO−. 

A rapidly responding and highly sensitive biosensor for pH-universal detection of ONOO− and its cellular imaging

A fluorescence turn-on switch induced by functional group conversion offers great potential in fluorescent probes and bioimaging due to its high specificity and efficiency. Exploring novel fluorescence turn-on switches and their singling mechanism are of great significance. In this manuscript, a novel fluorescent turn-on switch strategy induced by diketone isomerization was reported. It was found that when the diketone group of the synthesized coumarin derivative was converted into its monoketone or carboxylic acid derivatives, it could be illuminated. With this fluorescence turn-on strategy, the obtained probe could be used as a trigger for peroxynitrite (ONOO−). The imaging and monitoring of ONOO− in RAW 264.7 cells endogenously induced by acetaminophen and heat shock were successfully achieved. This diketone isomerization strategy will promote the design and construction of a series of novel redox probes.

A facile and highly efficient fluorescent turn-on switch strategy based on diketone isomerization and its application in peroxynitrite fluorescent imaging

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A facile and highly efficient fluorescent turn-on switch strategy based on diketone isomerization and its application in peroxynitrite fluorescent imaging