Recent advances and perspectives in reaction-based fluorescent probes for imaging peroxynitrite in biological systems

Cui, Wei-Long; Wang, Maohua; Yang, Yun-Hao; Wang, Jianyong; Zhu, Xiuzhong; Zhang, Haitao; Ji, Xingxiang

doi:10.1016/j.ccr.2022.214848

Cited by 65 publications

(12 citation statements)

References 107 publications

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“…[51] There is also growing interest to design novel organic fluorophores which could be potentially be used for sensing and cellular imaging applications. [52][53][54] The dyes which could be used for monitoring cellular viability and can distinguish live/ dead cells are of particular interest to track cellular metabolism. In this context, research group of Wang and co-workers have designed interesting organic fluorescent dyes which could specifically label lipid droplets and hence differentiate between dead and living zebra fish model.…”

Section: Introductionmentioning

confidence: 99%

An Isothiazolanthrone‐Based Self‐Assembling Anticancer Color‐Changing Dye for Concurrent Imaging and Monitoring of Cell Viability

Gour

Kshtriya

Khatun

et al. 2023

Chemistry An Asian Journal

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We report the photophysical properties, self‐assembly and biological evaluation of an isothiazolanthrone‐based dye, 7‐amino‐6H‐anthra[9,1‐cd]isothiazol‐6‐one (AAT), which reveals anticancer properties and can be potentially used as dye for monitoring cell viability. The solvent‐dependent photophysical studies suggest that the emission of AAT is sensitive to environment polarity due to which interesting changes in the colored emission may be observed owing to the charge transfer (CT) processes. AAT also self‐assembles to tree‐like branched morphologies and produce, a greenish emission inside the cells when imaged after short interval (15 mins) of incubation while a red fluorescence could be noted after 24 h. Interestingly, AAT also produce differential emission inside mouse normal cells as compared to its cancer cell lines since it possess anticancer activity. The experimental observations were also validated theoretically via computational modeling.

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Section: Introductionmentioning

confidence: 99%

An Isothiazolanthrone‐Based Self‐Assembling Anticancer Color‐Changing Dye for Concurrent Imaging and Monitoring of Cell Viability

Gour

Kshtriya

Khatun

et al. 2023

Chemistry An Asian Journal

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“…Recently, fluorescent probes have attracted more attention because of their merits of high sensitivity, simple operation, noninvasiveness, and real-time detection. − Coupled with microscopic imaging technology, a number of fluorescent probes for ONOO – detection have been reported. − Fluorescent probes with near-infrared (NIR, 650–900 nm) fluorescence responses can afford additional superiorities such as minimal background interference, deep penetration, and low damage to biological samples. − NIR fluorophores generally have a large pull–push π-conjugated structure to obtain low excited-state energy; however, the structural hallmark easily enables intermolecular aggregation through π–π interactions. − The aggregation accompanied by properties such as aggregation-caused quenching (ACQ) and poor water solubility is not conducive to detection in the biological system . Moreover, the elongated conjugative backbone of NIR fluorophores is readily decomposed by the strong oxidization ability of ONOO – , leading to the decrease of NIR fluorescence. ,− This photo-bleaching of NIR fluorophores induced by ONOO – is in conflict with the design of NIR ONOO – fluorescent probes because, in this design, ONOO – is expected to act on the reactive functionalities within the fluorophores to recover their NIR fluorescence and generate a turn-on fluorescence signal for ONOO – detection.…”

Section: Introductionmentioning

confidence: 99%

New “Destruction Seek to Survive” Strategy Based on a Serum Albumin Assembly with a Squaraine Molecule for the Detection of Peroxynitrite

et al. 2023

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Peroxynitrite (ONOO − ), a kind of active nitrogen species, plays an important role in biological systems. Overproduction of ONOO − is closely related to the pathogenesis of many diseases. Therefore, it is necessary to quantify intracellular ONOO − for differentiating health and disease states. Fluorescent probes with near-infrared (NIR) fluorescence can detect ONOO − with high sensitivity and selectivity. However, there is an inevitable problem that many NIR fluorophores are easily oxidized by ONOO − to give a false-negative result. To avoid this problem, herein, we ingeniously propose a "destruction to seek to survive" strategy to detect ONOO − . Two NIR squaraine (SQ) dyes were connected together to form a fluorescent probe (SQDC). This method utilizes the destructive effect of peroxynitrite on one of the SQ moieties of SQDC to eliminate the steric hindrance, enabling the other "survived" SQ segment to enter the hydrophobic cavity of bovine serum albumin (BSA) via the well-known host−guest interactions. The encapsulation of albumin protects the "survived" SQ from further attack of ONOO − . As a result, a NIR fluorescence turn-on response coming from the host−guest interaction between BSA and the "survived" SQ escaped from SQDC was found, which can be used for the detection of ONOO − . The assembly of SQDC mixed with BSA can be located in mitochondria to detect endogenous and exogenous ONOO − sensitively in living cells. As a proof-of-concept method, it is envisioned that this novel detection strategy with a simple assembly would become a powerful means for the detection of ONOO − when employing NIR fluorophores.

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“…Detections with fluorescent probes have become an ideal way for real-time monitoring of molecular events in living cells and in vivo ( Chen et al, 2017 ; Yin et al, 2019 ; Wang et al, 2021 ; Ji et al, 2023 ). Although a variety of rationally designed fluorescent probes specifically for Cys or pH have been reported in recent years ( Guo et al, 2019 ; Ajayaghosh et al, 2020 ; Kikuchi et al, 2020 ; Wang et al, 2020 ; Chen et al, 2021 ; Yamaguchi et al, 2021 ; Lin et al, 2022 ), the separate detection of Cys and pH in the same detection system leads to differences in probe localizations, the different metabolisms of the probes, and the failure to elucidate signaling pathways ( James et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

A cascading-response fluorescent probe for real-time pH monitoring during cysteine-depletion process in pancreatic cancer cells

Qin

Zhang

Guo

et al. 2022

Front. Bioeng. Biotechnol.

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Pancreatic cancer (PC) is one of the deadliest human malignancies, and exploring the complex molecular mechanisms behind cell death will greatly promote the clinical treatment of PC. Here, we reported a cascading-response fluorescent-imaging probe, Cy-Cys-pH, for the sequential detection of cysteine (Cys) and pH in pancreatic cancer cells. In the presence of Cys, Cys-mediated cleavage of the acrylate group caused Cy-Cys-pH to be transformed into Cy-Cys-O, which induced intense fluorescence enhancement at 725 nm. Then, Cy-Cys-O was protonated to obtain Cy-Cys-OH and the fluorescence emission shifted to 682 nm, showing a ratiometric pH response. Furthermore, Cy-Cys-pH can monitor the intracellular pH during the therapeutic process with anticancer drugs and evaluated the ability of three anticancer drugs to kill Panc-1 cells, proving that associating Cys and pH is in part an effective anticancer strategy in the treatment of pancreatic cancer. Significantly, Cy-Cys-pH is able to monitor and image pH changes during Cys depletion in real-time, which further reveals the molecular mechanism of Cys-depleted pancreatic cancer cell death, providing a powerful molecular tool for the precise treatment of PC.

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Recent advances and perspectives in reaction-based fluorescent probes for imaging peroxynitrite in biological systems

Cited by 65 publications

References 107 publications

An Isothiazolanthrone‐Based Self‐Assembling Anticancer Color‐Changing Dye for Concurrent Imaging and Monitoring of Cell Viability

An Isothiazolanthrone‐Based Self‐Assembling Anticancer Color‐Changing Dye for Concurrent Imaging and Monitoring of Cell Viability

New “Destruction Seek to Survive” Strategy Based on a Serum Albumin Assembly with a Squaraine Molecule for the Detection of Peroxynitrite

A cascading-response fluorescent probe for real-time pH monitoring during cysteine-depletion process in pancreatic cancer cells

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