2015

DOI: 10.1039/c4cc07411d

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A fast-responsive mitochondria-targeted fluorescent probe detecting endogenous hypochlorite in living RAW 264.7 cells and nude mouse

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Abstract: A very fast-responsive fluorescent probe PZ-Py for imaging mitochondrial HClO/ClO(-), with a relatively long emission wavelength, was prepared. The limit of detection was evaluated to be 17.9 nM. Moreover, the probe PZ-Py was successfully applied in the imaging of endogenous HClO/ClO(-) in the mitochondria of RAW 264.7 cells and living nude mouse.

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Cited by 225 publications

(71 citation statements)

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“…In recent years, fluorescence imaging technique based on chemical probe make the in situ tissue quantification possible 12 , a precondition of which is the need to design a rapid and sensitive probe for the target. Many excellent chemical probes have been devised to monitor the ROS molecules like ClO -in various biological samples [13][14][15][16][17][18] .…”

Section: Introductionmentioning

confidence: 99%

In situ quantification and evaluation of ClO⁻/H₂S homeostasis in inflammatory gastric tissue by applying a rationally designed dual-response fluorescence probe featuring a novel H⁺-activated mechanism

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Homeostasis of ClO -/H2S plays crucial role in the damage and repair of gastric tissue, but has been rarely investigated due to the challenge of in situ analysis in the highly acidic gastric environment. Herein, we design a new H + -activated optical mechanism including the controllable photo-induced electron transfer (PET) and the switch of electron push-pull (SEPP) to develop the simple yet multifunctional probe (

“…In recent years, fluorescence imaging technique based on chemical probe make the in situ tissue quantification possible 12 , a precondition of which is the need to design a rapid and sensitive probe for the target. Many excellent chemical probes have been devised to monitor the ROS molecules like ClO -in various biological samples [13][14][15][16][17][18] .…”

Section: Introductionmentioning

confidence: 99%

In situ quantification and evaluation of ClO⁻/H₂S homeostasis in inflammatory gastric tissue by applying a rationally designed dual-response fluorescence probe featuring a novel H⁺-activated mechanism

¹

,

²

,

³

et al. 2017

View full text Add to dashboard Cite

Homeostasis of ClO -/H2S plays crucial role in the damage and repair of gastric tissue, but has been rarely investigated due to the challenge of in situ analysis in the highly acidic gastric environment. Herein, we design a new H + -activated optical mechanism including the controllable photo-induced electron transfer (PET) and the switch of electron push-pull (SEPP) to develop the simple yet multifunctional probe (

“…As shown in Figure S6, upon the addition of HOCl into the aqueous solution of PQI , the molecular ion peak of [ PQI ] + at m / z= 423.1905 was disappeared. A new peak at m / z= 439.1848 was obtained, which can be assigned to the oxidized sulfoxide product, PQI‐O . The result indicated that the HOCl‐induced oxidation of thiazine thioetherto sulfoxide is responsible for the HOCl sensing mechanism.…”

Section: Resultsmentioning

confidence: 99%

Responsive Fluorescence Probe for Selective and Sensitive Detection of Hypochlorous Acid in Live Cells and Animals

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et al. 2018

Chemistry An Asian Journal

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The development of effective bioanalytical methods for rapid, sensitive and specific detection of HOCl in vitro and in vivo plays a key role for better understanding the roles of this molecule in normal and diseased conditions, but remains challenging due to the highly reactive nature of HOCl and the complicated biological conditions. In this work, a new fluorescence probe, PQI, was developed for monitoring of the HOCl level in biological samples. PQI was easily synthesized by a one-step condensation reaction. Upon addition of HOCl, significant changes in the absorption spectra and the color of the solution were noticed, facilitating the "naked eye" detection of HOCl in PBS buffer. The fluorescence of PQI was found to be significantly increased within a few seconds, leading to "OFF-ON" fluorescence response towards HOCl. The sensing mechanism, oxidation of thioether by HOCl, was confirmed by HRMS titration analysis. PQI features a large Stokes shift, high sensitivity and selectivity, and rapid fluorescence response towards HOCl. Quantitative detection of HOCl in single live cells was demonstrated through fluorescence imaging and flow cytometry analysis. PQI was then successfully used in visualisation of HOCl in live zebrafish and nude mice.

“…Another sulfide‐based fluorescent probe for the selective detection of HOCl was reported by Wang and co‐workers in 2015 (Scheme ) . The methylated pyridinium group of the chemical probe exhibits not only a new type of effective mitochondria‐targeting group (due to the positive charge within the molecule), but also assists in the water‐solubility of the organic fragment of the molecule.…”

Section: Introductionmentioning

confidence: 99%

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

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et al. 2019

Chemistry An Asian Journal

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In recent decades, HOCl research has attracted a lot of scientists from around the world. This chemical species is well known as an important player in the biological systems of eukaryotic organisms including humans. In the human body, HOCl is produced by the myeloperoxidase enzyme from superoxide in very low concentrations (20 to 400 μm); this species is secreted by neutrophils and monocytes to help fight pathogens. However, in the condition called “oxidative stress”, HOCl has the capability to attack many important biomolecules such as amino acids, proteins, nucleotides, nucleic acids, carbohydrates, and lipids; these reactions could ultimately contribute to a number of diseases such as neurodegenerative diseases (AD, PD, and ALS), cardiovascular diseases, and diabetes. In this review, we discuss recent efforts by scientists to synthesize various fluorophores which are attached to receptors to detect HOCl such as: chalcogen‐based oxidation, oxidation of 4‐methoxyphenol, oxime/imine, lactone ring opening, and hydrazine. These synthetic molecules, involving rational synthetic pathways, allow us to chemoselectively target HOCl and to study the level of HOCl selectivity through emission responses. Virtually all the reports here deal with well‐defined and small synthetic molecular systems. A large number of published compounds have been reported over the past years; this growing field has given scientists new insights regarding the design of the chemosensors. Reversibility, for example is considered important from the stand point of chemosensor reuse within the biological system; facile regenerability using secondary analytes to obtain the initial probe is a very promising avenue. Another aspect which is also important is the energy of the emission wavelength of the sensor; near‐infrared (NIR) emission is favorable to prevent autofluorescence and harmful irradiation of tissue; thus, extended applicability of such sensors can be made to the mouse model or animal model to help image internal organs. In this review, we describe several well‐known types of receptors that are covalently attached to the fluorophore to detect HOCl. We also discuss the common fluorophores which are used by chemist to detect HOCl, Apart from the chemical aspects, we also discuss the capabilities of the compounds to detect HOCl in living cells as measured through confocal imaging. The growing insight from HOCl probing suggests that there is still much room for improvement regarding the available molecular designs, knowledge of interplay between analytes, biological applicability, biological targeting, and chemical switching, which can also serve to further sensor and theurapeutic agent development alike.

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