Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Yue, Yongkang; Huo, Fangjun; Yin, Caixia; Escobedo, Jorge O.; Strongin, Robert M.

doi:10.1039/c6an00158k

Cited by 169 publications

(69 citation statements)

References 69 publications

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“…It is now apparent that the previously reported decrease in fluorescence intensity during Cl À oxidation was likely due to fluorescence quenching and not to desalination. [55] We conclude that electrochemical Cl À oxidation does not form a significant IDZ or electric field gradient in solution that can be used for saltwater desalination. Furthermore, these findings demonstrate that undesired (or unknown) electrochemical and chemical processes can prevent formation of an IDZ and electric field gradient in other electrochemical systems.…”

Section: Discussionmentioning

confidence: 80%

“…Second, the ECP gradient measured during electrochemical Cl − oxidation is caused by a shift in the chemical potential, rather than the electric potential, of the solution in the vicinity of the anode. It is now apparent that the previously reported decrease in fluorescence intensity during Cl − oxidation was likely due to fluorescence quenching and not to desalination …”

Section: Discussionmentioning

confidence: 89%

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Effect of Chloride Oxidation on Local Electric Fields in Microelectrochemical Systems

2019

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We recently reported that electrochemical oxidation of Cl− to neutral Cl2 decreases solution conductivity, thereby yielding a local electric field gradient. Here, we report detailed experimental results and simulations indicating that the situation is more complex than we originally thought. The key new findings are twofold. First, once generated, Cl2 rapidly reacts with water to form ionic species that increase, rather than decrease, solution conductivity near the anode. Second, the electrochemical potential gradient measured in the vicinity of the anode during Cl− oxidation is dominated by differences in the chemical potential, rather than the electrical potential, of the solution. These findings clarify the electrochemical and chemical processes previously reported to enable desalination via faradaic Cl− oxidation.

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Section: Discussionmentioning

confidence: 80%

Section: Discussionmentioning

confidence: 89%

Effect of Chloride Oxidation on Local Electric Fields in Microelectrochemical Systems

2019

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“…Recently studies revealed that this molecule is an important microbicidal agent during immune inflammation response, corresponding to the digestion of the bacterium engulfed by neutrophil phagosome . However, overbalance of HOCl production during inflammation is implicated with many diseases, including Alzheimer disease, cardiovascular disease, atherosclerosis, ischemia‐reperfusion injury in stroke, osteoarthritis, inflammatory bowel disease, myocardial infarction, organ transplant rejection, and even cancers …”

Section: Introductionmentioning

confidence: 98%

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

Feng

Meng

Wang

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.

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“…However, more than 100 reports have been published in the literature regarding this single analyte (Scheme ). There is still room to develop an excellent probe for detection of this ROS; importantly, R. Strongin and co‐workers reported the first review article which covered the recent progress in chromogenic and fluorogenic chemosensors for HOCl (2016) . Recently, the D. Yang group has reported coverage for the fluorescent probes for HOCl imaging .…”

Section: Introductionmentioning

confidence: 99%

“…There is still room to develop an excellent probe for detection of this ROS;importantly,R.Strongin and co-workersr eported the first review article which covered the recent progress in chromogenic and fluorogenic chemosensors forH OCl (2016). [18] Recently,t he D. Yang group has reported coverage for the fluorescent probes for HOCl imaging. [19] In both earlier reports, the authorsh ad not covered extensively all reports of HOCl detection.…”

Section: Introductionmentioning

confidence: 99%

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

Yudhistira

Mulay

Kim

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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Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Cited by 169 publications

References 69 publications

Effect of Chloride Oxidation on Local Electric Fields in Microelectrochemical Systems

Effect of Chloride Oxidation on Local Electric Fields in Microelectrochemical Systems

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

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

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