A highly specific fluorescent probe for hypochlorite based on fluorescein derivative and its endogenous imaging in living cells

Wang, Bihui; Chen, Dan; Srinivasulu, K.; Wang, Fang; Wang, Yong; Zhang, Wei; Yin, Jun; Chen, Haiyan; Chen, Xiaoqiang

doi:10.1016/j.dyepig.2015.03.022

Cited by 92 publications

(24 citation statements)

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“…So, a lot of effort has been devoted to develop ClO − sensors in the past decade, with various functional moieties like thioether, 19 thioester, [20][21][22] thione, 23,24 p-methoxy, 25,26 hydrazide, 27,28 oxime, 29,30 selenide, 31,32 and C=N bond. [33][34][35] Chemodosimeter is a molecular probe that recognizes analytes with the irrevocable process. [36][37][38][39][40] It has the advantage of high selectivity with little interference of other anions, so it has been frequently studied in anion sensing area.…”

Section: Introductionmentioning

confidence: 99%

An imine-based colorimetric chemodosimeter for the detection of hypochlorite $$(\hbox {ClO}^{-})$$ in aqueous media: its application in test strips and real water samples

2019

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A highly selective colorimetric chemodosimeter ASAD, (E)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)-5-methoxybenzenesulfonic acid, was readily synthesized and characterized. The probe ASAD could selectively recognize hypochlorite (ClO −) through an oxidative cleavage of C=N bond with a color change from yellow to colorless and detected it down to a low concentration of 0.95 μM. Importantly, ASAD could be employed as a practical and efficient optical sensor for ClO − in test strips and water samples. Moreover, the detection process of ASAD to hypochlorite was demonstrated by UV-vis spectroscopy, NMR titration and theoretical calculations.

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Section: Introductionmentioning

confidence: 99%

An imine-based colorimetric chemodosimeter for the detection of hypochlorite $$(\hbox {ClO}^{-})$$ in aqueous media: its application in test strips and real water samples

2019

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“…The probe contains both C=Na nd hydrazine groups which are used together for the first time to detect HOCl. [87] The reaction between the probe and HOCl is very fast (within 5s); changes of the solution from pink to light yellow followed. Upon the reactionw ith HOCl, an increasei nt he fluorescence quantumy ield was measured from F F = 0.01 to F F = 0.58;e mission intensity was linear in relationship when using an HOCl concentration range of 0-30 mm and involved adetection limit of 7.3 nm (S/N = 3).…”

Section: Scheme77mentioning

confidence: 99%

“…Chen and co‐workers reported in 2015 the fluorescein‐based selective and sensitive probe for the detection of HOCl (Scheme ). The probe contains both C=N and hydrazine groups which are used together for the first time to detect HOCl . The reaction between the probe and HOCl is very fast (within 5 s); changes of the solution from pink to light yellow followed.…”

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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“…Nowadays, fluorescent probes have been evaluated as one of the most indispensable tools for monitoring trace amounts of biological species in practical application, as their prominent tissue permeability, wonderful specificity, superb sensitivity, high spatial resolution, rapid response time, easiness of manipulating, less cell‐damage and real‐time detection . Among the probes based on coumarin, rhodamine, tetraphenylethylene, fluorescein and naphthalimide were constantly emerged, while they may be influenced by instrument efficiency, poor stability for oxidants, environmental conditions, inferior detection limit and weak anti‐interference over other species .…”

Section: Introductionmentioning

confidence: 99%

A Fluorescent Probe with a Significant Selective Turn‐On Response for HClO Detection and Bioimaging in Living Cells

et al. 2019

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Hypochlorous/Hypochlorite(HClO/ClO À ) plays an important biochemistry roles in normal operation of the life system. Herein, a fluorescent probe 7-chloro-3-((E)-3-(4-(dimethylamino)phenyl)acryloyl)-2H-chromen-2-one (CCO) was rationally designed and synthesized via aldehyde ketone condensation reaction to detect ClO À in Tris-HCl (pH = 7.2, 60% DMF) solution. Probe CCO was cleaved conceivably in the coumarin lactone ring by an oxidation reaction with ClO À and emitted intensive bright yellow fluorescence. The sensing mechanism was further confirmed by ESI-MS and DFT calculation. The fluorescence emission of probe CCO triggered by ClO À was obviously enhanced within 20 s. The limit of detection of probe CCO was calculated as low as 2.6 nM. Furthermore, probe CCO can be given as an effective and outstanding fluorescent exogenous ClO À probe in living HEK293T cells for microscopic cell imaging.

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A highly specific fluorescent probe for hypochlorite based on fluorescein derivative and its endogenous imaging in living cells

Cited by 92 publications

References 50 publications

An imine-based colorimetric chemodosimeter for the detection of hypochlorite $$(\hbox {ClO}^{-})$$ in aqueous media: its application in test strips and real water samples

An imine-based colorimetric chemodosimeter for the detection of hypochlorite $$(\hbox {ClO}^{-})$$ in aqueous media: its application in test strips and real water samples

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

A Fluorescent Probe with a Significant Selective Turn‐On Response for HClO Detection and Bioimaging in Living Cells

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