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Pharmaceuticals (Basel). 2016 Jul 8;9(3). pii: E43. doi: 10.3390/ph9030043.

Convergent Synthesis of Two Fluorescent Ebselen-Coumarin Heterodimers.

Author information

1
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany. jim.kueppers@uni-bonn.de.
2
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany. anna.schulz-fincke@uni-bonn.de.
3
Department of Organic Chemistry, Wrocław University of Technology (A2), Wyspiańskiego 27, 50-370 Wrocław, Poland. jerzy.palus@pwr.wroc.pl.
4
Department of Organic Chemistry, Wrocław University of Technology (A2), Wyspiańskiego 27, 50-370 Wrocław, Poland. miroslaw.giurg@pwr.wroc.pl.
5
Department of Organic Chemistry, Wrocław University of Technology (A2), Wyspiańskiego 27, 50-370 Wrocław, Poland. jacek.skarzewski@pwr.wroc.pl.
6
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany. guetschow@uni-bonn.de.

Abstract

The organo-seleniumdrug ebselen exhibits a wide range of pharmacological effects that are predominantly due to its interference with redox systems catalyzed by seleno enzymes, e.g., glutathione peroxidase and thioredoxin reductase. Moreover, ebselen can covalently interact with thiol groups of several enzymes. According to its pleiotropic mode of action, ebselen has been investigated in clinical trials for the prevention and treatment of different ailments. Fluorescence-labeled probes containing ebselen are expected to be suitable for further biological and medicinal studies. We therefore designed and synthesized two coumarin-tagged activity-based probes bearing the ebselen warhead. The heterodimers differ by the nature of the spacer structure, for which-in the second compound-a PEG/two-amide spacer was introduced. The interaction of this probe and of ebselen with two cysteine proteases was investigated.

KEYWORDS:

coumarin; ebselen; heterodimer

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