Published January 1, 2025 | Version v1
Journal article Open

Synthesis and Evaluation of <i>Pseudo</i>glucosinolates Releasing Isothiocyanates in the Presence of Azoreductases

  • 1. Univ Gothenburg, Dept Chem & Mol Biol, Medicinaregatan 7B, S-41390 Gothenburg, Sweden
  • 2. Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany
  • 3. Helmholtz Ctr Infect Res, Dept Chem Biol, Inhoffenstr 7, D-38124 Braunschweig, Germany
  • 4. Tech Univ Carolo Wilhelmina Braunschweig, Inst Biochem Biotechnol & Bioinformat, Spielmannstr 7, D-38106 Braunschweig, Germany

Description

Naturally occurring isothiocyanates (ITCs) display multiple interesting bioactivities, but their medicinal exploitation is very limited as ITCs are non-druglike compounds with problematic pharmacokinetic properties. The concept of pseudoglucosinolates provides a novel prodrug approach for the release of ITCs which can be adjusted to different triggers such as enzymatic and chemical microenvironments. Herein, the first adaptation of this concept toward the release of ITCs in the presence of azoreductases within a turn-on fluorescence probe is reported and its applicability in covalent protein labeling is underlined.

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