Selective Detection and Visualization of Exogenous/endogenous Hypochlorous Acid in Living Cells using a BODIPY‐based Red‐emitting Fluorescent Probe

Wang, Xianhui; Tao, Yuanfang; Zhang, Jian; Chen, Miao; Wang, Nannan; Ji, Xin; Zhao, Weili

doi:10.1002/asia.201901709

Cited by 19 publications

(7 citation statements)

References 66 publications

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“…Through a benzyl pyridinium cleavable unit at meso position of BODIPY, probe 23 was developed for detection of HOCl. Upon addition of HOCl, it exhibits a fastresponsive rate and a dramatic red fluorescence increase (λ em = 614 nm, 170-fold) with high selectivity and sensitivity (LOD = 60 × 10 −9 mol dm −3 ) [40].…”

Section: Sensing Applicationsmentioning

confidence: 99%

Advances in Pyridyl-Based Fluorophores for Sensing Applications

Leite¹,

Queirós²,

Silva³

2023

Exploring Chemistry With Pyridine Derivatives

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Fluorescence sensing plays an important role in high sensitivity, selectivity, and real-time monitoring of biological and environmentally relevant species. Several classes of fluorescent dyes (fluorophores) including rhodamine, BODIPY, 1,8-naphthalimide, and coumarin-among others−when conveniently functionalized with reactive pyridyl receptors, have emerged as effective sensors to detect and quantify chemical species with high accuracy through fluorescent imaging and spectroscopy. Among the sensing targets, monitoring of harmful chemical species, e.g., metal ions (zinc, copper, iron, mercury, cadmium, lead, etc.) and anions (chloride, fluoride, sulfide, thiocyanate, etc.) can be used to understand their physiological and pathological role in live-cells and tissues, as well as to protect human health. This chapter focuses on recent advances in the molecular design of pyridyl-substituted fluorophores, their photophysical properties, and sensing applications.

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Section: Sensing Applicationsmentioning

confidence: 99%

Advances in Pyridyl-Based Fluorophores for Sensing Applications

Leite¹,

Queirós²,

Silva³

2023

Exploring Chemistry With Pyridine Derivatives

View full text Add to dashboard Cite

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“…The selection of HClO-sensitive functional groups includes pmethoxyphenol, [12] hydroxylamine [13] and chalcogenide. [14] Among them, the fluorescent probes with aldoxime group conjugated with BODIPY, [15][16][17][18][19][20] rhodamine, [21] and phenanthroline [22] have exhibited great response. In particular, the aldoxime group can react with HClO to generate aldehyde, carboxylic acid, or nitrile oxide, which leads to the structure convert oriented emission change.…”

Section: Introductionmentioning

confidence: 99%

A BODIPY‐Based Far‐Red‐Absorbing Fluorescent Probe for Hypochlorous Acid Imaging

Wan

Wang

et al. 2022

ChemPhotoChem

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Hypochlorous acid (HClO) is produced by white blood cells to defend against injury and bacteria. However, as one of the reactive oxygen species, high intracellular HClO concentration could lead to chronic diseases that affect the cardiovascular and nervous systems. To monitor HClO concentrations in bio‐samples, the fluorescent probe is preferred to have: a) Absorbability in the far‐red window with reduced light toxicity and improved tissue penetration depth; b) Ratiometric features for accurate analysis. In this study, we reported a far‐red ratiometric HClO fluorescence probe based on BODIPY chromophore and aldoxime sensing group. Not only the color change of the probe solution can be detected by the naked eye, but also the emission ratios (I645/I670) showed a significant increase upon the introduction of HClO. More importantly, the feasibility of HClO monitoring in biosamples was demonstrated in vitro using a confocal microscope.

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“…Among various kinds of analytical methods, fluorescent probes can detect HOCl in biological organisms in real-time and in situ, so several fluorophore-based fluorescent probes, including coumarin [ 18 , 19 , 20 , 21 , 22 , 23 ], BODIPY [ 24 , 25 , 26 , 27 , 28 , 29 ], rhodamine [ 30 , 31 , 32 , 33 , 34 , 35 ], naphthalimide [ 36 , 37 , 38 , 39 , 40 , 41 ], etc., have been developed for imaging HOCl in vitro and in vivo [ 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ]. The detection mechanism is primarily the oxidation reaction of HOCl with p -alkoxyaniline, p -methoxyphenol, oxime, hydrazine, electron-deficient C=C bonds, and S/Se/Te, resulting in fluorescence signals “on” or “off” [ 53 , 54 ].…”

Section: Introductionmentioning

confidence: 99%

A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid

et al. 2022

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Hypochlorous acid (HOCl) is a reactive substance that reacts with most biomolecules and is essential in physiological and pathological processes. Abnormally elevated HOCl levels may cause inflammation and other disease responses. To further understand its key role in inflammation, HOCl must be detected in situ. Here, we designed a hydroxytricyanopyrrole-based small-molecule fluorescent probe (HTCP-NTC) to monitor and identify trace amounts of HOCl in biological systems. In the presence of HOCl, HTCP-NTC released hydroxyl groups that emit strong fluorescence covering a wide wavelength range from the visible to near-infrared region owing to the resumption of the intramolecular charge transfer process. Additionally, HTCP-NTC demonstrated a 202-fold fluorescence enhancement accompanied by a large Stokes shift and a low detection limit (21.7 nM). Furthermore, HTCP-NTC provided a rapid response to HOCl within 18 s, allowing real-time monitoring of intracellular HOCl. HTCP-NTC exhibited rapid kinetics and biocompatibility, allowing effective monitoring of the exogenous and endogenous HOCl fluctuations in living cells. Finally, based on fluorescence imaging, HTCP-NTC is a potential method for understanding the relationship between inflammation and HOCl.

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Selective Detection and Visualization of Exogenous/endogenous Hypochlorous Acid in Living Cells using a BODIPY‐based Red‐emitting Fluorescent Probe

Cited by 19 publications

References 66 publications

Advances in Pyridyl-Based Fluorophores for Sensing Applications

Advances in Pyridyl-Based Fluorophores for Sensing Applications

A BODIPY‐Based Far‐Red‐Absorbing Fluorescent Probe for Hypochlorous Acid Imaging

A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid

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