A simple and reversible fluorescent probe based on NBD for rapid detection of hypochlorite and its application for bioimaging

Shen, Youming; Zhang, Xiangyang; Huang, Xi; Wen, Siyu; Liu, Mingdi; Deng, Yan; Zhang, Youyu; Zhang, Chunxiang; Jin, Jun‐Ling; Li, Haitao; Yao, Shouzhuo

doi:10.1039/c5ra15373e

Cited by 28 publications

(7 citation statements)

References 50 publications

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“…Due to the PET from Se to coumarin, CM1 showed fluorescence "OFF" in PBS buffer. In the presence of HOCl, the fluorescence of CM1 was switched "ON" within seconds, making it a good candidate for real-time By employing other fluorophores [105,123,[193][194][195][196][197][198][199][200], such as pyrene [87,88,201], phenanthroline [94,202], phenothiazine [100,[203][204][205], carbazole [93], NBD [206][207][208], MB [209], TPE [210], benzothiazole [211,212], phenanthroimidazole [96,213], and cyanine (Cy) [119,214]…”

Section: <Fig 8 Is Here>mentioning

confidence: 99%

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Zhang

Song

Yuan

2018

TrAC Trends in Analytical Chemistry

228

115

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Hypochlorous acid (HOCl), a well-known universal disinfectant in clinical practice, plays important roles in immune systems of animal and human bodies. For understanding the roles of HOCl in living systems, a number of approaches, including chemiluminescence, colorimetric, electrochemical and chromatographic methods have been explored. For the detection of HOCl in live organisms, cuttingedge techniques, such as fluorescence/phosphorescence molecular probes, responsive nanoprobes, Raman and activatable photoacoustic sensors, have also been developed recently. In this review, the recent advances in the development of bioanalytical methods for detection of HOCl in environmental and biological specimens were summarized. More specifically, traditional techniques for assay of HOCl in bulk solution were initially discussed, and then fluorescence molecular probes, phosphorescence probes, responsive nanoprobes and other methods for HOCl detection were reviewed, which gives an overview of the developments and applications in bioanalytical methods for HOCl detection.

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Section: <Fig 8 Is Here>mentioning

confidence: 99%

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Zhang

Song

Yuan

2018

TrAC Trends in Analytical Chemistry

228

115

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“…Zhang et al reported the Se-containing reversible HOCl probe 38 based on 7-nitrobenz-2-oxa-1,3-diazole (NBD). [50] This probe shows highly selective, sensitive (low detection limit of 3.3 nM) and rapid (within 10 s), as well as reversible recognition to hypochlorite in the presence of GSH. Se oxidation suppresses the d-PeT process from the selenide to NBD in the excited state, making the turn-on fluorescence response of probe 38 to happen.…”

Section: Eurjocmentioning

confidence: 99%

Reversible Reaction‐Based Fluorescent Probes for Dynamic Sensing and Bioimaging

2020

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Diverse chemical species such as ions and molecules exist within living cells and organisms undergoing dynamic changes in their local environment by a web of continuously interacting reactions. Reaction‐based fluorescent probes with a highly sought reversible feature can provide a real‐time monitor of the concentration dynamics (increases and decreases) of such chemical species, thus ideally suited to understand the physiological function, and pathogenic mechanisms of corresponding bio‐species in the regulation of cellular function and disease progression. This review summarizes the current methods for constructing reversible reaction‐based fluorescent probes. The sensing mechanisms and biological applications of these probes are also discussed. The representative examples reported recently are categorized according to the type of reversible chemical reactions utilized: nucleophilic additions (Michael additions, chromophore reactions), nucleophilic addition‐condensation reactions, and redox reactions. Finally, we present the potential challenges and suggestions for developing probes based on dynamic and reversible covalent bond formation reactions.

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“…Zhang and co-workersd escribed the small and reversible probe based on 7-nitrobenz-2-oxa-1,3-diazole as af luorescent moiety and selenomorpholine as ar eactive site on the probe which quenches the fluorescenceb yw ay of aP ET process (Scheme 24). [54] Because of the PET effect imparted by the selenomorpholine probe is weakly fluorescent, it therefore shows a" turn-on" response after reaction with HOCl, and again a "turn-off" response with GSH. The reversible redoxc ycle of the probe was demonstrated (up to four times in repetition) under the same conditions suggesting adequate stabilityo ft he probe which could be used to detect the oxidant in question Scheme20.…”

Section: Oxidation Of Organochalogen To Their Tetravalent (E = O) Oxidesmentioning

confidence: 99%

“…Zhang and co‐workers described the small and reversible probe based on 7‐nitrobenz‐2‐oxa‐1,3‐diazole as a fluorescent moiety and selenomorpholine as a reactive site on the probe which quenches the fluorescence by way of a PET process (Scheme ) . Because of the PET effect imparted by the selenomorpholine probe is weakly fluorescent, it therefore shows a “turn‐on” response after reaction with HOCl, and again a “turn‐off” response with GSH.…”

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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A simple and reversible fluorescent probe based on NBD for rapid detection of hypochlorite and its application for bioimaging

Abstract: A simple and reversible fluorescent probe bearing 7-nitrobenz-2-oxa-1,3-diazole and a selenomorpholine fragment was designed and synthesized.

Cited by 28 publications

References 50 publications

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Reversible Reaction‐Based Fluorescent Probes for Dynamic Sensing and Bioimaging

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

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