Evaluation of Ebselen-azadioxatriangulenium as redox-sensitive fluorescent intracellular probe and as indicator within a planar redox optode

Koren, Klaus; Salinas, Nina Katharina Gravesen; Santella, Marco; Moßhammer, Maria; Müller, Marie-Caroline; Dmitriev, Ruslan I.; Borisov, Sergey; Kühl, Michael; Laursen, Bo W.

doi:10.1016/j.dyepig.2019.107866

Cited by 11 publications

(8 citation statements)

References 52 publications

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“…Recently, Koren et al combined the ebselen group with azadioxatriangulenium (ADOTA) dye to synthesize the probe Ebselen-ADOTA and studied its potential application in redox detection inside and outside the cell. 58 Similar to the response mechanism reported by Mugesh's group, 57 the probe Ebselen-ADOTA reacted with H 2 O 2 and added one or two oxygen atoms to the Se atom of the ebselen parent to generate fluorescence (Figure 7A). The probe can effectively stain mammalian cells and bacterial cells (Figure 7B), and there is a significant effect on the oxidative stress fluorescence signal produced by anaerobic bacteria in oxygen, which can reach the maximum after 37 min (Figure 7C).…”

Section: Biochemical Applicationssupporting

confidence: 56%

Section: Biochemical Applicationsmentioning

confidence: 92%

“…Of course, if ebselen interacts with H 2 O 2 first, another cycle can be carried out: first, under the oxidation of H 2 O 2 , an oxygen atom is added to the selenium atom to generate selenoamide compound 4 , and then a selenite compound 5 is generated by removing a molecule of water and finally return to ebselen through the reduction of GSH to complete the cycle. Following the principle of the ebselen involved redox cycles, it is rational that the combination of benzoselenazole and fluorophore can make probes toward RSS or ROS. − Their work mechanisms are often based on the open or close of benzoselenazole ring under the stimulation of GSH or H 2 O 2 , which changes the photoinduced electron transfer (PET) effect of ebselen part to the fluorophore, and further causes a observable fluorescence response.…”

Section: Biochemical Applicationsmentioning

confidence: 99%

“…(b) Fluorescence (detected at >550 nm) of a redox optode mounted in a flow-through system and exposed to various amounts of oxidant (H 2 O 2 ) and reductant (AA). Reproduced with permission from ref . Copyright 2019 Elsevier.…”

Section: Biochemical Applicationsmentioning

confidence: 99%

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Ebselen-Agents for Sensing, Imaging and Labeling: Facile and Full-Featured Application in Biochemical Analysis

Zhang

Lei

Wang

et al. 2021

ACS Appl. Bio Mater.

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Phenyl-1,2-benzoselenazol-3(2H)-one (ebselen) is a classical mimic of glutathione peroxidase (GPx). Thioredoxin interaction endows ebselen attractive biological functions, such as antioxidation and anti-infection, as well as versatile therapeutic usage. Accordingly, application of ebselen analogues in biosensing, chemical labeling, imaging analysis, disease pathology, drug development, clinical treatment, etc. have been widely developed, in which mercaptans, reactive oxygen species, reactive sulfur species, peptides, and proteins were involved. Herein, focusing on the application of ebselen-agents in biochemistry, we have made a systematic summary and comprehensive review. First, we summarized both the classical and the innovative methods for preparing ebselen-agents to present the synthetic strategies. Then we discussed the full functional applicability of ebselen analogues in three fields of biochemical analysis including the fluorescence sensing and bioimaging, derivatization for high throughput fluorescence analysis, and the labeling gents for proteomics. Finally, we discussed the current challenges and perspectives for ebselen-agents as analytical tools in biological research. By presenting the multifunctional applicability of ebselen, we hope this review could appeal researchers to design the ebselen-related biomaterials for biochemical analysis.

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Section: Biochemical Applicationssupporting

confidence: 56%

Section: Biochemical Applicationsmentioning

confidence: 92%

Section: Biochemical Applicationsmentioning

confidence: 99%

Section: Biochemical Applicationsmentioning

confidence: 99%

See 2 more Smart Citations

Ebselen-Agents for Sensing, Imaging and Labeling: Facile and Full-Featured Application in Biochemical Analysis

Zhang

Lei

Wang

et al. 2021

ACS Appl. Bio Mater.

View full text Add to dashboard Cite

show abstract

“…Is an environment reduced or oxidized? While this question is often asked in redox biology, , optodes that respond to a changing redox environment have not been available until very recently . Such optodes should be further developed and applied in studying heterogeneous environments where oxidants and reductants are consumed or produced locally (e.g., biofilms).…”

Section: How Can We Unravel the Full Potential Of Optode Based Chemic...mentioning

confidence: 99%

Optode Based Chemical Imaging—Possibilities, Challenges, and New Avenues in Multidimensional Optical Sensing

Koren

Zieger

2021

ACS Sens.

Self Cite

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Seeing is believing, as the saying goes, and optical sensors (so-called optodes) are tools that can make chemistry visible. Optodes react reversibly and quickly (seconds to minutes) to changing analyte concentrations, enabling the spatial and temporal visualization of an analyte in complex environments. By being available as planar sensor foils or in the form of nano-or microparticles, optodes are flexible tools suitable for a wide array of applications. The steadily grown applications of in particular oxygen (O 2 ) and pH optodes in fields as diverse as medical, environmental, or material sciences is proof for the large demand of optode based chemical imaging. Nevertheless, the full potential of this technology is not exhausted yet, challenges have to be overcome, and new avenues wait to be taken. Within this Perspective, we look at where the field currently stands, highlight several successful examples of optode based chemical imaging and ask what it will take to advance current state-of-the-art technology. It is our intention to point toward some potential blind spots and to inspire further developments.

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Time‐Resolved Luminescent Sensing and Imaging for Enzyme Catalytic Activity Based on Responsive Probes

Wang

Jin

et al. 2022

Chemistry An Asian Journal

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Enzymes, as a kind of biomacromolecules, play an important role in many physiological processes and relate directly to various diseases. Developing an efficient detection method for enzyme activity is important to achieve early diagnosis of enzyme-relevant diseases and high throughput screening of potential enzyme-relevant drugs. Time-resolved luminescence assay provide a high accuracy and signal-tonoise ratios detection methods for enzyme activity, which has been widely used in high throughput screening of enzyme-relevant drugs and diagnosis of enzyme-relevant diseases. Inspired by these advantages, various responsive probes based on metal complexes and metal-free organic compounds have been developed for time-resolved bioimaging and biosensing of enzyme activity owing to their long luminescence lifetimes, high quantum yields and photostability. In this review, we comprehensively reviewed metal complex-and metal-free organic compound-based responsive probes applied to detect enzyme activity through timeresolved imaging, including their design strategies and sensing principles. Current challenges and future prospects in this rapidly growing field are also discussed.

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Evaluation of Ebselen-azadioxatriangulenium as redox-sensitive fluorescent intracellular probe and as indicator within a planar redox optode

Cited by 11 publications

References 52 publications

Ebselen-Agents for Sensing, Imaging and Labeling: Facile and Full-Featured Application in Biochemical Analysis

Ebselen-Agents for Sensing, Imaging and Labeling: Facile and Full-Featured Application in Biochemical Analysis

Optode Based Chemical Imaging—Possibilities, Challenges, and New Avenues in Multidimensional Optical Sensing

Time‐Resolved Luminescent Sensing and Imaging for Enzyme Catalytic Activity Based on Responsive Probes

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