Sydnthiones are versatile bioorthogonal hydrogen sulfide donors.

ABSTRACT: Hydrogen sulfide (H₂S) is an important endogenous gasotransmitter, but the bioorthogonal reaction triggered H₂S donors are still rare. Here we show one type of bioorthogonal H₂S donors, sydnthiones (1,2,3-oxadiazol-3-ium-5-thiolate derivatives), which was designed with the aid of density functional theory (DFT) calculations. The reactions between sydnthiones and strained alkynes provide a platform for controllable, tunable and mitochondria-targeted release of H₂S. We investigate the reactivity of sydnthiones‒dibenzoazacyclooctyne (DIBAC) reactions and their orthogonality with two other bioorthogonal cycloaddition pairs: tetrazine‒norbornene (Nor) and tetrazine‒monohydroxylated cyclooctyne (MOHO). By taking advantage of these mutually orthogonal r

SUBMITTER: Xu W 

PROVIDER: S-EPMC11603141 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature