Convergent Synthesis of Two Fluorescent Ebselen-Coumarin Heterodimers

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.

Synthesis of new alkylated and methoxylated analogues of ebselen with antiviral and antimicrobial properties

“…31 Alternatively, disodium diselenide in protic medium (MeOH) can be used to introduce the diselenide moiety, however the yield was reported to be lower (18-67 %). 24,32 The procedure for preparation of disodium diselenide is critical to obtain 2,2'-diselenobisbenzoic acid (2) with good yields. The type of reducing agent, such as hydrazine monohydrate, 24 and sodium tetrahydroborate 21 as well as reaction times up to 48 hours, are of particular importance.…”

Cell‐permeable high‐affinity tracers for Gq proteins provide structural insights, reveal distinct binding kinetics and identify small molecule inhibitors

“…Ebselen was synthesized following reported procedures (Küppers et al, ; Pietka‐Ottlik, Potaczek, Piasecki, & Mlochowski, ). BIM‐46174 and BIM‐46178 were synthesized as described (Schmitz et al, ).…”

“…Ebselen was synthesized following reported procedures (Küppers et al, 2016;Pietka-Ottlik, Potaczek, Piasecki, & Mlochowski, 2010).…”

Novel [(3-Nitro-2-Oxo-2h-Chromen-4-Ylamino)-Phenyl]phenyl-Azetidin-2-Ones and Their Antimicrobial Activity

“…15 According to that, many of them have found widespread usage in pharmacies. 16 On the other hand, azetidin-2-one derivatives reported having a wide range of biological activities, 17 including those antimicrobial, 18 anti-fungal, 19 anti-convulsant, 20 and anti-HIV activity. 21 The biological activity of these derivatives is conditioned by their structure, so the presence of different substituents on the benzopyrone ring indicates their impact on the type and potency of biological activity.…”