Hydrogen sulfide (H2S) is known for its distinct smell and has been shown to play an important role in many different biological functions. Most of the H2S produced in the body originates from the reaction of cysteine with the enzymes cystathionine beta-synthase and cystathionine gamma-lyase. These enzymes facilitate the production of H2S in many biological systems including the neuronal, cardiovascular, respiratory, liver, immune, renal, gastrointestinal, reproductive, and endocrine systems.  A slow, steady release of nanomolar to micromolar concentrations of H2S is important for its applications as therapies in biological systems because H2S is toxic at concentrations of 100 mM. Although small molecules are known to deliver H2S by hydrolysis in water or by reaction with enzymes, no polymers are known that degrade to release H2S. We developed the first synthesis of polymers based on poly(lactic acid) that contain functional groups known to release H2S in cells. These polymers release H2S over prolonged periods of time and at steady rates. The monomers were synthesized by attaching lactide to H2S-releasing molecules � allyl sulphide and 4-hydoxybenzothioamide � using a thiol-ene reaction and formation of a disulfide bond. The monomers polymerized under mild condition using DMAP as a catalyst. These polymers were readily fabricated into microparticles which released H2S.

Synthesis of a biodegradable hydrogen sulfide releasing polymer

246th National Meeting (2013)

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