A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging

Nguyen, Van‐Nghia; Heo, Seonye; Kim, Sangin; Swamy, K. M.K.; Ha, Jeongsun; Park, Sungnam; Yoon, Juyoung

doi:10.1016/j.snb.2020.128213

Cited by 51 publications

(24 citation statements)

References 30 publications

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“…The obtained main product ( DSM ′) was confirmed with DIM by 1 H NMR, 13 C NMR, and ESI-HRMS ( Supplementary Figures S35, S36B ). Furthermore, DSM was highly sensitive to ClO − , with a detection limit (LOD) of 0.13 µM ( Supplementary Figure S50B ), which is lower than that of many ClO − probes in previous reports ( Xiao et al, 2015 ; Shen et al, 2017 ; Wang et al, 2018 ; Lee S. C. et al, 2020 ; Nguyen et al, 2020 ).…”

Section: Resultsmentioning

confidence: 69%

“…Among the various reactive oxygen species (ROS), hypochlorite (HOCl/ClO − ) acts as a powerful microbicidal agent in the innate immune system. ClO − is mainly produced by the myeloperoxidase (MPO)-catalyzed reaction of H 2 O 2 and Cl − in immunocytes ( Domigan et al, 1995 ; Xu et al, 2013 ; Pak et al, 2018 ; Wu et al, 2019 ; Nguyen et al, 2020 ). The regulated production of microbicidal HOCl is required for the host to control invading microbes.…”

Section: Introductionmentioning

confidence: 99%

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Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

et al. 2021

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The ability to detect hypochlorite (HOCl/ClO−) in vivo is of great importance to identify and visualize infection. Here, we report the use of imidazoline-2-thione (R1SR2) probes, which act to both sense ClO− and kill bacteria. The N2C=S moieties can recognize ClO− among various typical reactive oxygen species (ROS) and turn into imidazolium moieties (R1IR2) via desulfurization. This was observed through UV–vis absorption and fluorescence emission spectroscopy, with a high fluorescence emission quantum yield (ՓF = 43–99%) and large Stokes shift (∆v∼115 nm). Furthermore, the DIM probe, which was prepared by treating the DSM probe with ClO−, also displayed antibacterial efficacy toward not only Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) but also methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum ß-lactamase–producing Escherichia coli (ESBL-EC), that is, antibiotic-resistant bacteria. These results suggest that the DSM probe has great potential to carry out the dual roles of a fluorogenic probe and killer of bacteria.

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Section: Resultsmentioning

confidence: 69%

Section: Introductionmentioning

confidence: 99%

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

et al. 2021

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“…In addition to the determination of metals, in many cases coumarin derivatives are used as fluorescence probes for the detection of hypochlorite, as in the case of coumarin–thiophene complexes ( Figure 8 , compound XLVI ) [ 70 ] or of 2-thiocoumarins in which the presence of ClO– allows the formation of a fluorescent coumarin ( Figure 8 , compound XLVII ) [ 71 ].…”

Section: Discussionmentioning

confidence: 99%

Trending Topics on Coumarin and Its Derivatives in 2020

et al. 2021

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Coumarins are naturally occurring molecules with a versatile range of activities. Their structural and physicochemical characteristics make them a privileged scaffold in medicinal chemistry and chemical biology. Many research articles and reviews compile information on this important family of compounds. In this overview, the most recent research papers and reviews from 2020 are organized and analyzed, and a discussion on these data is included. Multiple electronic databases were scanned, including SciFinder, Mendeley, and PubMed, the latter being the main source of information. Particular attention was paid to the potential of coumarins as an important scaffold in drug design, as well as fluorescent probes for decaging of prodrugs, metal detection, and diagnostic purposes. Herein we do an analysis of the trending topics related to coumarin and its derivatives in the broad field of drug discovery.

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“… 14 However, the various reactive oxygen species (ROSs) produced by PSs or other oxides perform single-atom sulfur-for-oxygen replacements, which bring about the inactivation of the PSs, implying that these PSs are not stable under light and cannot be reused. 15 Twisted π-conjugation systems 16 and orthogonal compact electron donor–acceptor dyads 17 have also been used to facilitate the ISC process, which also lead to relatively short absorption wavelengths. Based on the aggregation-induced emission (AIE) skeleton, the D–π–A strategy has been proven to be an efficient way to enhance ISC for AIE PS construction.…”

Section: Introductionmentioning

confidence: 99%

New Cy5 photosensitizers for cancer phototherapy: a low singlet–triplet gap provides high quantum yield of singlet oxygen

Long

Cao

et al. 2021

Chem. Sci.

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A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging

Cited by 51 publications

References 30 publications

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

Trending Topics on Coumarin and Its Derivatives in 2020

New Cy5 photosensitizers for cancer phototherapy: a low singlet–triplet gap provides high quantum yield of singlet oxygen

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