Hydrogen sulfide (HS) is a mediator of a number of cellular processes, and modulating cellular levels of this gas has emerged as an important therapeutic area. Localized generation of HS is thus very useful but highly challenging. Here, we report pivaloyloxymethyl-based carbonothioates and carbamothioates that are activated by the enzyme, esterase, to generate carbonyl sulfide (COS), which is hydrolyzed to HS.

Enhancement of hydrogen sulfide in bacteria reveals a key role for this gas in mediating antibiotic resistance.

Generation of hydrogen sulfide (HS) is challenging and few methods are capable of localized delivery of this gas. Here, a boron dipyrromethene-based carbamothioate (BDP-HS) that is uncaged by visible light of 470 nm to generate carbonyl sulfide (COS), which is rapidly hydrolyzed to HS in the presence of carbonic anhydrase, a widely prevalent enzyme, is reported.

A series of carbamothioates with tunable release of HS after activation by reactive oxygen species are reported. The half-lives of HS release could be tuned from 24 to 203 min by varying the basicity of the amine.