A near-infrared endoplasmic reticulum-targeted fluorescent probe to visualize the fluctuation of SO2 during endoplasmic reticulum stress

Yue, Lizhou; Huang, Huawei; Song, Wenhui; Lin, Weiying

doi:10.1016/j.cej.2021.133468

Cited by 49 publications

(17 citation statements)

References 40 publications

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“…It was logical to verify that the dimalononitrile isophorone moiety was helpful for ER-specific localization of ISO-Chy. 43,44 These results demonstrated that ISO-Chy could be used to monitor the bioactivity of CHT in the ER of living cells and tumors.…”

Section: Resultsmentioning

confidence: 83%

Activatable endoplasmic reticulum-targeted NIR fluorescent probe with a large Stokes shift for detecting and imaging chymotrypsin

Lan

Tian

et al. 2022

Analyst

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Section: Resultsmentioning

confidence: 83%

Activatable endoplasmic reticulum-targeted NIR fluorescent probe with a large Stokes shift for detecting and imaging chymotrypsin

Lan

Tian

et al. 2022

Analyst

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“…Reactive-species-induced ER stress and its association with ER-related diseases have drawn significant attention and concerns. Following the discovery that SO 2 has the functionality to inhibit ER stress [ 124 ], Yue et al designed a probe, MSO-SO 2 ( 34 , Scheme 5 ), with which to detect SO 2 produced during ER stress induced by dithiothreitol (DTT) [ 125 ]. Due to the good ER-targeting ability of dimalononitrile isophorone derivatives, the authors selected levulinic acid as the specific recognition site for SO 2 , as well as a weak electron withdrawing group, and constructed an ER-targeted NIR fluorescent probe based on the dicyanoisophorone framework, realizing directly the visualization of the production as well as consumption of SO 2 during DTT-induced ER stress.…”

Section: Design Of Molecular Probes For Organelle-targeted Cell Imagingmentioning

confidence: 99%

Recent Development of Advanced Fluorescent Molecular Probes for Organelle-Targeted Cell Imaging

Dai

Cui

et al. 2023

Biosensors

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Fluorescent molecular probes are very powerful tools that have been generally applied in cell imaging in the research fields of biology, pathology, pharmacology, biochemistry, and medical science. In the last couple of decades, numerous molecular probes endowed with high specificity to particular organelles have been designed to illustrate intracellular images in more detail at the subcellular level. Nowadays, the development of cell biology has enabled the investigation process to go deeply into cells, even at the molecular level. Therefore, probes that can sketch a particular organelle’s location while responding to certain parameters to evaluate intracellular bioprocesses are under urgent demand. It is significant to understand the basic ideas of organelle properties, as well as the vital substances related to each unique organelle, for the design of probes with high specificity and efficiency. In this review, we summarize representative multifunctional fluorescent molecular probes developed in the last decade. We focus on probes that can specially target nuclei, mitochondria, endoplasmic reticulums, and lysosomes. In each section, we first briefly introduce the significance and properties of different organelles. We then discuss how probes are designed to make them highly organelle-specific. Finally, we also consider how probes are constructed to endow them with additional functions to recognize particular physical/chemical signals of targeted organelles. Moreover, a perspective on the challenges in future applications of highly specific molecular probes in cell imaging is also proposed. We hope that this review can provide researchers with additional conceptual information about developing probes for cell imaging, assisting scientists interested in molecular biology, cell biology, and biochemistry to accelerate their scientific studies.

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“…A key feature for the HSA protein is its hydrophobic cavity, where the binding of HSA with small molecules would significantly perturb the local environment of the molecular probe. In this regard, fluorophores such as the dicyanoisophorone-based type were particularly interesting as their optical properties were strongly dependent to their environmental changes such as polarity or viscosity. − Herein, a dual-channel responsive fluorescent probe M–OH–SO 3 with a large Stokes’ shift was prepared, consisting of a fluorescent reporter (dicyanoisophorone), a dinitrobenzenesulfonate ester moiety, and the hydroxymethyl group (regulator), which exhibited yellow (575 nm) and red (660 nm) emission for HSA under excitations at 400 and 500 nm, respectively (Scheme ). The response of the probe toward HSA was optimized by screening a series of functional groups at the ortho position of the phenol moiety, where the probe with the hydroxymethyl group ( M–OH–SO 3 ) possesses the best performance.…”

Section: Introductionmentioning

confidence: 99%

Dual-Channel Recognition of Human Serum Albumin and Glutathione by Fluorescent Probes with Site-Dependent Responsive Features

Yuan

Pan

et al. 2022

Anal. Chem.

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Design of chemical probes with high specificity and responses are particularly intriguing. In this work, a fluorescent probe (M–OH–SO 3 ) with dual-channel spectral responses toward human serum albumin (HSA) is presented. By employing dinitrobenzenesulfonate as a recognition site as well as a fluorescence quencher, probe M–OH–SO 3 displayed weak fluorescence, which, nevertheless, exhibits extensive yellow (575 nm) and red (660 nm) fluorescence emissions toward HSA under excitations at 400 and 500 nm, respectively. Interestingly, M–OH–SO 3 displayed the best performance toward HSA with distinctly higher selectivity than that of its counterparts M–SO 3 , M–H–SO 3 , and M–F–SO 3 , which were prepared simply by modulating the functional group at the ortho position of the dicyanoisophorone core. Molecular docking results revealed that M–OH–SO 3 possesses the lowest binding energy among the tested derivatives and accordingly the strongest binding affinity. Probe M–OH–SO 3 showed a good linear relationship toward HSA in a range of 0.5–18 μM with a limit of detection of 35 nM. Cell imaging results demonstrated that probe M–OH–SO 3 could visualize the variation HSA levels in hepatocarcinoma cells. In addition, probe M–OH–SO 3 could also be employed for the recognition of glutathione through the cleavage of the dinitrobenzenesulfonate group along with an enhancement of emission at 575 nm. The site-dependent properties inspired a novel paradigm for design of fluorescent probes with optimized selectivity and responses.

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A near-infrared endoplasmic reticulum-targeted fluorescent probe to visualize the fluctuation of SO2 during endoplasmic reticulum stress

Cited by 49 publications

References 40 publications

Activatable endoplasmic reticulum-targeted NIR fluorescent probe with a large Stokes shift for detecting and imaging chymotrypsin

Activatable endoplasmic reticulum-targeted NIR fluorescent probe with a large Stokes shift for detecting and imaging chymotrypsin

Recent Development of Advanced Fluorescent Molecular Probes for Organelle-Targeted Cell Imaging

Dual-Channel Recognition of Human Serum Albumin and Glutathione by Fluorescent Probes with Site-Dependent Responsive Features

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