Sulfur-based fluorescent probes for HOCl: Mechanisms, design, and applications

Hou, Ji‐Ting; Kwon, Nahyun; Wang, Shan; Wang, Bingya; He, Xiaojun; Yoon, Juyoung; Shen, Jianliang

doi:10.1016/j.ccr.2021.214232

Cited by 139 publications

(59 citation statements)

References 119 publications

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“…The kinetic data for this class of probes are, however, very limited. The third class of probes is based on a rapid reaction of a thiol group with HOCl, producing a sulfenyl chloride intermediate, which undergoes further reactions to produce a fluorescent product, via a mechanism depending on the chemical design of the probe 20 , 41 – 43 .…”

Section: Introductionmentioning

confidence: 99%

Fluorescent probes for monitoring myeloperoxidase-derived hypochlorous acid: a comparative study

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Pięta

Rola

et al. 2022

Sci Rep

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MPO-derived oxidants including HOCl contribute to tissue damage and the initiation and propagation of inflammatory diseases. The search for small molecule inhibitors of myeloperoxidase, as molecular tools and potential drugs, requires the application of high throughput screening assays based on monitoring the activity of myeloperoxidase. In this study, we have compared three classes of fluorescent probes for monitoring myeloperoxidase-derived hypochlorous acid, including boronate-, aminophenyl- and thiol-based fluorogenic probes and we show that all three classes of probes are suitable for this purpose. However, probes based on the coumarin fluorophore turned out to be not reliable indicators of the inhibitors’ potency. We have also determined the rate constants of the reaction between HOCl and the probes and they are equal to 1.8 × 104 M−1s−1 for coumarin boronic acid (CBA), 1.1 × 104 M−1s−1 for fluorescein based boronic acid (FLBA), 3.1 × 104 M−1s−1 for 7-(p-aminophenyl)-coumarin (APC), 1.6 × 104 M−1s−1 for 3’-(p-aminophenyl)-fluorescein (APF), and 1 × 107 M−1s−1 for 4-thiomorpholino-7-nitrobenz-2-oxa-1,3-diazole (NBD-TM). The high reaction rate constant of NBD-TM with HOCl makes this probe the most reliable tool to monitor HOCl formation in the presence of compounds showing HOCl-scavenging activity.

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Section: Introductionmentioning

confidence: 99%

Fluorescent probes for monitoring myeloperoxidase-derived hypochlorous acid: a comparative study

Pierzchała

Pięta

Rola

et al. 2022

Sci Rep

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“…[17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] To date, several HOCl responsive fluorescent probes have been reported based on well-known fluorophore small molecules as well as using DNA-based technologies. [34][35][36][37][38][39] Several reported activity-based fluorescent probes (ABFP) are limited by their synthetic difficulties, modulation of the optical properties, aqueous solubility, and especially organelle targeting ability. We recently developed unique pentacyclic-based IndiFluors with full visible color-tunability with high quantum yields and good aqueous solubility.…”

Section: Introductionmentioning

confidence: 99%

An efficient PeT based fluorescent probe for mapping mitochondrial oxidative stress produced via the Nox2 pathway

et al. 2022

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“…Amongst the various analytical methods, fluorescence imaging technology has been considered as a potentially powerful method for tracing active species in biological systems due to its simplicity, sensitivity, real-time, and non-destructive detection. [22][23][24][25][26][27][28][29][30][31][32][33] Therefore, myriad ONOO À -responsive fluorescent probes suitable for fluorescence imaging have been fabricated that have greatly promoted the understanding of ONOO À biology. [34] Most ONOO À -sensitive fluorescent probes display a fluorescence-intensity response at a single wavelength, which is susceptible to technical limitations caused by various interfering factors such as detection environment, probe concentration and photobleaching.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Progress of Small‐Molecule Ratiometric Fluorescent Probes for Peroxynitrite in Biological Systems

Zhai

et al. 2022

Chemistry A European J

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Peroxynitrite (ONOO À ) as a major reactive oxygen species plays important roles in cellular signal transduction and homeostatic regulation. Precise detection of ONOO À in biological systems is vital for exploring its physiological and pathological function. Among numerous detection methods, fluorescence imaging technology using fluorescent probes offers some advantages, including simple operation, high sensitivity and selectivity, as well as real-time and nondestructive detection. In particular, ratiometric fluorescent probes, in which the built-in calibration of the two emission bands prevents interference from the biological environment, have been extensively employed to monitor the fluctuation of bioactive species. In this review, we will discuss smallmolecule ratiometric fluorescent probes for ONOO À in live cells or in vivo, which involves chemical structures, response mechanisms, and biological applications. Moreover, the challenges and future prospects of ONOO À -responsive ratiometric fluorescent probe are also proposed.

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Sulfur-based fluorescent probes for HOCl: Mechanisms, design, and applications

Cited by 139 publications

References 119 publications

Fluorescent probes for monitoring myeloperoxidase-derived hypochlorous acid: a comparative study

Fluorescent probes for monitoring myeloperoxidase-derived hypochlorous acid: a comparative study

An efficient PeT based fluorescent probe for mapping mitochondrial oxidative stress produced via the Nox2 pathway

Recent Progress of Small‐Molecule Ratiometric Fluorescent Probes for Peroxynitrite in Biological Systems

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