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

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

doi:10.1016/j.dyepig.2019.107866

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

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

2 Citations (Scopus)

Abstract

Redox homeostasis is essential for cellular survival and is therefore tightly regulated. Visualizing changes in the local redox state is essential for detecting oxidative stress, especially with the help of red, long emission lifetime probes. We synthesized a new reversible, redox-sensitive fluorescent probe, ebselen-azadioxatriangulenium (Ebselen-ADOTA), and characterized its potential use for intra- and extracellular redox sensing. The probe consists of a photostable triangulenium-based fluorophore (emission maximum at 564 nm) modulated by a redox-active ebselen motif. The reduced form only shows around 1/10 of the emission intensity of the oxidized form. The Ebselen-ADOTA probe exhibited reversible oxidation and reduction in solution under extracellular conditions. In addition, Ebselen-ADOTA can visualize an increase in oxidative stress within anaerobic bacteria when exposing them to air, the probe did not readily respond to changes in the redox environment inside mammalian cells, probably due to unfavorable localization, aggregation or binding to cysteine containing proteins. When incorporated inside a polymer matrix (hydrogel D4 mixed with poly(acrylic acid)), the probe showed a rapid and fully reversible response to redox changes, thus enabling the preparation of a redox-sensitive optode.

Original language	English
Article number	107866
Journal	Dyes and Pigments
Volume	173
Number of pages	9
ISSN	0143-7208
DOIs	https://doi.org/10.1016/j.dyepig.2019.107866
Publication status	Published - Feb 2020

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Koren, K., Salinas, N. K. G., Santella, M., Moßhammer, M., Müller, M.-C., Dmitriev, R. I., Borisov, S. M., Kühl, M., & Laursen, B. W. (2020). Evaluation of Ebselen-azadioxatriangulenium as redox-sensitive fluorescent intracellular probe and as indicator within a planar redox optode. Dyes and Pigments, 173, Article 107866. https://doi.org/10.1016/j.dyepig.2019.107866

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

abstract = "Redox homeostasis is essential for cellular survival and is therefore tightly regulated. Visualizing changes in the local redox state is essential for detecting oxidative stress, especially with the help of red, long emission lifetime probes. We synthesized a new reversible, redox-sensitive fluorescent probe, ebselen-azadioxatriangulenium (Ebselen-ADOTA), and characterized its potential use for intra- and extracellular redox sensing. The probe consists of a photostable triangulenium-based fluorophore (emission maximum at 564 nm) modulated by a redox-active ebselen motif. The reduced form only shows around 1/10 of the emission intensity of the oxidized form. The Ebselen-ADOTA probe exhibited reversible oxidation and reduction in solution under extracellular conditions. In addition, Ebselen-ADOTA can visualize an increase in oxidative stress within anaerobic bacteria when exposing them to air, the probe did not readily respond to changes in the redox environment inside mammalian cells, probably due to unfavorable localization, aggregation or binding to cysteine containing proteins. When incorporated inside a polymer matrix (hydrogel D4 mixed with poly(acrylic acid)), the probe showed a rapid and fully reversible response to redox changes, thus enabling the preparation of a redox-sensitive optode.",

author = "Klaus Koren and Salinas, {Nina Katharina Gravesen} and Marco Santella and Maria Mo{\ss}hammer and Marie-Caroline M{\"u}ller and Dmitriev, {Ruslan I.} and Borisov, {Sergey M.} and Michael K{\"u}hl and Laursen, {Bo W.}",

year = "2020",

month = feb,

doi = "10.1016/j.dyepig.2019.107866",

language = "English",

volume = "173",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Pergamon Press",

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TY - JOUR

T1 - Evaluation of Ebselen-azadioxatriangulenium as redox-sensitive fluorescent intracellular probe and as indicator within a planar redox optode

AU - Koren, Klaus

AU - Salinas, Nina Katharina Gravesen

AU - Santella, Marco

AU - Moßhammer, Maria

AU - Müller, Marie-Caroline

AU - Dmitriev, Ruslan I.

AU - Borisov, Sergey M.

AU - Kühl, Michael

AU - Laursen, Bo W.

PY - 2020/2

Y1 - 2020/2

N2 - Redox homeostasis is essential for cellular survival and is therefore tightly regulated. Visualizing changes in the local redox state is essential for detecting oxidative stress, especially with the help of red, long emission lifetime probes. We synthesized a new reversible, redox-sensitive fluorescent probe, ebselen-azadioxatriangulenium (Ebselen-ADOTA), and characterized its potential use for intra- and extracellular redox sensing. The probe consists of a photostable triangulenium-based fluorophore (emission maximum at 564 nm) modulated by a redox-active ebselen motif. The reduced form only shows around 1/10 of the emission intensity of the oxidized form. The Ebselen-ADOTA probe exhibited reversible oxidation and reduction in solution under extracellular conditions. In addition, Ebselen-ADOTA can visualize an increase in oxidative stress within anaerobic bacteria when exposing them to air, the probe did not readily respond to changes in the redox environment inside mammalian cells, probably due to unfavorable localization, aggregation or binding to cysteine containing proteins. When incorporated inside a polymer matrix (hydrogel D4 mixed with poly(acrylic acid)), the probe showed a rapid and fully reversible response to redox changes, thus enabling the preparation of a redox-sensitive optode.

AB - Redox homeostasis is essential for cellular survival and is therefore tightly regulated. Visualizing changes in the local redox state is essential for detecting oxidative stress, especially with the help of red, long emission lifetime probes. We synthesized a new reversible, redox-sensitive fluorescent probe, ebselen-azadioxatriangulenium (Ebselen-ADOTA), and characterized its potential use for intra- and extracellular redox sensing. The probe consists of a photostable triangulenium-based fluorophore (emission maximum at 564 nm) modulated by a redox-active ebselen motif. The reduced form only shows around 1/10 of the emission intensity of the oxidized form. The Ebselen-ADOTA probe exhibited reversible oxidation and reduction in solution under extracellular conditions. In addition, Ebselen-ADOTA can visualize an increase in oxidative stress within anaerobic bacteria when exposing them to air, the probe did not readily respond to changes in the redox environment inside mammalian cells, probably due to unfavorable localization, aggregation or binding to cysteine containing proteins. When incorporated inside a polymer matrix (hydrogel D4 mixed with poly(acrylic acid)), the probe showed a rapid and fully reversible response to redox changes, thus enabling the preparation of a redox-sensitive optode.

U2 - 10.1016/j.dyepig.2019.107866

DO - 10.1016/j.dyepig.2019.107866

M3 - Journal article

SN - 0143-7208

VL - 173

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 107866

ER -

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

Abstract

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