5 years ago

Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes

Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes
Luke A. Connal, Thomas Bonnard, Daniel E. Heath, Joe Collins, Zeyun Xiao, Aida Shakouri-Motlagh, Jonathan White, Christoph E. Hagemeyer, Ross A. L. Wylie
Hydrogen sulfide (H2S) has been identified as an important cell-signaling mediator and has a number of biological functions, such as vascular smooth muscle relaxation, neurotransmission, and regulation of inflammation. A facile and versatile approach for H2S production initiated by light irradiation and controlled by reaction with an amine or an amino acid was developed. The donor was synthesized in a one-pot reaction, and simple crystallization led to a yield of approximately 90 %. The synthetic strategy is scalable and versatile, and the H2S donors can be expressed ina number of different molecular and macromolecular forms, including crystalline small-molecule compounds, water-soluble polymers, polystyrene films, and hydrogels. The H2S donors based on polystyrene film and hydrogel were used as cell-culture scaffolds. The H2S donor based on water-soluble polymer was applied in photocontrolled inhibition of P-selectin expression on human platelets and subsequent regulation of platelet aggregation. This study provides the simplest controllable H2S source to study its biological functions. The developed materials are also new therapeutic platforms to deliver H2S, as there is no accumulation of toxic byproducts, and the donor materials from polystyrene films and hydrogels can be readily removed after releasing H2S. Dual-trigger H2S donors: A facile and versatile approach to H2S release has been developed by trapping photogenerated thiobenzaldehydes with amines. The H2S release process can be controlled with light and an amine. In addition to a crystalline small-molecule H2S donor, water-soluble polymer, polystyrene film, and hydrogel H2S donors were easily obtained. The new materials showed excellent biocompatibility and were used for controlled delivery of H2S to cells and antiplatelet applications (see scheme).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701206

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