Synthesis of nitric oxide-releasing polyurethanes with S-nitrosothiol-containing hard and soft segments

Abstract

Nitric oxide (NO)-releasing polyurethanes capable of releasing up to 0.20 μmol NO cm−2 were synthesized by incorporating active S-nitrosothiol functionalities into hard and soft segment domains using thiol group protection and post-polymerization modifications, respectively. The nitrosothiol position within the hard and soft segment domains of the polyurethanes impacted both the total NO release and NO release kinetics. The NO storage and release properties were correlated to both chain extender modification and ensuing phase miscibility of the polyurethanes. Thorough material characterization is provided to examine the effects of hard and soft segment modifications on the resultant polyurethane properties.

Nitric oxide release: Part I. Macromolecular scaffolds

“…63 Likewise, S -nitrosothiol NO donors have been covalently linked to polyester 64, 65 and polyurethane. 66 For a more detailed description of NO-releasing polymers the reader is directed to reviews by Frost et al, 11 Hetrick and Schoenfisch, 12 and Varu et al 13 …”

Protected thiol strategies in macromolecular design

“…However, when adding acetic anhydride, part of the deprotected thiols were transformed into thioacetate groups and thus crosslinking could be prevented. Schoenfisch and co-workers [152] used the trityl protective group to shield a thiol-containing monomer for the synthesis of functional polyurethanes. The thiols were recovered by reaction with TFA, after which they were converted in S-nitrosothiols, to serve as nitric oxide-releasing materials.…”

Polymer‐Based Nitric Oxide Therapies: Recent Insights for Biomedical Applications

“…Coneski and Schoenfisch also used thiol groups to develop NO-releasing polyurethanes with NO release values up to 0.20 μmol cm −2 . [97] …”