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

ABSTRACT: 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.

SUBMITTER: Knight JR

PROVIDER: S-EPMC7736145 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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

Knight Jessica Renee JR Wang Yingying Y Xu Shi S Chen Wei W Berkman Clifford E CE Xian Ming M

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20201013

A unique reaction between thiols (RSH) and alkyl sulfonylbenzothiazole was discovered. This reaction was specific for thiols and produced a sulfinic acid (RSO<sub>2</sub>H) 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. ...[more]

PMID: 33128946

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