Synthesis and Evaluation of Pseudoglucosinolates Releasing Isothiocyanates in the Presence of Azoreductases

Abstract

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.

Keywords: pseudo glucosinolates; artificial glucosinolates; azoreductase; bio‐responsive protein labelings; isothiocyanates.