Synthesis and evaluation of pseudoglucosinolates (psGSLs) releasing isothiocyanates (ITCs) in the presence of azoreductases

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 (psGSLs) provides a novel prodrug approach for the release of ITCs which can be adjusted to different triggers such as enzymatic and chemical microenvironments. Here, we report the first adaptation of this concept towards the release of ITCs in the presence of azoreductases within a turn-on fluorescence probe and underline its applicability in covalent protein labelling.