A modular template for the design of thiol-triggered sensors and prodrugs.

A unique reaction between thiols (RSH) and alkyl sulfonylbenzothiazole was discovered. This reaction was specific for thiols and produced a sulfinic acid (RSO2H) as the intermediate, which further triggered an intramolecular cyclization to release a-OH containing payload. This reaction was used to develop thiol-triggered fluorescent sensors and prodrugs. The modular design of this template provides tunability of the release profiles of the payloads. (C) 2020 Elsevier B.V. All rights reserved.