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 M.; Kuhl, Michael; Laursen, Bo W.

doi:10.1016/j.dyepig.2019.107866

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

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

MPS-Authors

/persons/resource/persons257446

Müller, Marie-Caroline
IMPRS MarMic, Max Planck Institute for Marine Microbiology, Max Planck Society;

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Koren, K., Salinas, N. K. G., Santella, M., Mosshammer, M., Müller, M.-C., Dmitriev, R. I., et al. (2020). Evaluation of Ebselen-azadioxatriangulenium as redox-sensitive fluorescent intracellular probe and as indicator within a planar redox optode. Dyes and Pigments, 173: 107866. doi:10.1016/j.dyepig.2019.107866.

Cite as: https://hdl.handle.net/21.11116/0000-0006-411C-2

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.