Biodegradable citrate-based polyesters with S-nitrosothiol functional groups for nitric oxide release

Abstract

Herein, we report the synthesis and characterization of biodegradable citrate-based polyesters that were functionalized for nitric oxide release. The material extracts did not exhibit cytotoxicity as evaluated with human dermal fibroblasts.

Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO)

“…These include micelles, 138,190,191 microbubbles, 192 proteins, 193–197 liposomes, 126,198 inorganic nanoparticles (such as silica, 70,199–203 gold, 204,205 microparticles, 198,206 zeolites, 207,208 ), metal-organic frameworks (MOFs), 209–212 dendrimers, 71,213,214 xerogels, 215–217 electrospun fibers, 88,100,218 natural polymers (chitosan, 85–87,219–221 gelatin, 222 etc. ), and other organic polymers (polymethacrylate, 223 polyester, 224,225 polydimethylsiloxane (PDMS), 226 polysaccharides, 227,228 hydrogel, 178,179,229,230 PVA, 49,231,232 polyurethanes, 161,162,233,234 and PVC 154 ). The approaches and benefits of different NO-delivery materials have been highlighted in numerous reviews.…”

“…These include micelles, 139,191,192 microbubbles, 193 proteins, [194][195][196][197][198] liposomes, 127,199 inorganic nanoparticles (such as silica, 71,[200][201][202][203][204] gold 205,206 ), microparticles, 199,207 zeolites, 208,209 metal-organic frameworks (MOFs), [210][211][212][213] dendrimers, 72,214,215 xerogels, [216][217][218] electrospun fibers, 89,101,219 natural polymers (chitosan, [86][87][88][220][221][222] gelatin, 223 etc. ), and other organic polymers (polymethacrylate, 224 polyester, 225,226 polydimethylsiloxane (PDMS), 227 polysaccharides,…”

“…Lastly, several biodegradable polymers, such as citratebased 226 or saccharide-based polymers (e.g., dextran 228,245 and chitosan 87,88,221 ) provide very attractive scaffolds for NO delivery because of their natural occurrence, biodegradability, tolerability to mammalian cells and accessibility for NO donor functionalization reactions. 221,245,246 Reynolds and coworkers synthesized two S-nitrosated dextran thiomers (dextran-cystamine and dextran-cysteine), with up to 0.205 ± 0.003 μmol per mg NO loading and the capability to release NO for 6 h in PBS buffer at 37 °C.…”

Biodegradable crosslinked polyesters derived from thiomalic acid and S-nitrosothiol analogues for nitric oxide release

“…Three polyesters, PTMO, PTCO and PTO were synthesized from a combination of thiomalic acid, citric acid, maleic acid, and 1,8-octanediol following a modified literature protocol to yield crosslinked polyesters. 16, 26 In particular, thiomalic acid was included in order to avoid the use of coupling reactions to incorporate the thiol moiety. These thiol pendant groups serve as functionalization sites to form S -nitrosothiols.…”

Nitric Oxide–Releasing Macromolecular Scaffolds for Antibacterial Applications

“…Although several strategies describing the synthesis of biodegradable synthetic polymers either chemically modified with NO donors or prepared as polymeric nanoparticles for the encapsulation of NO-releasing small molecules have been reported, the majority of these materials are limited to polyesters such as poly(lactic-co-glycolic acid), [56] poly(sulfhydrylated polyester) [57] , poly(glycerol-co-glutaric acid), [58] and poly(citric-co-maleic acid-co-1,8-octanediol). [59] Reynolds and co-workers have worked to expand this area by developing S -nitrosothiol-modified poly(organophosphazenes) (POP) systems that can degrade hydrolytically into non-toxic phosphate and ammonia. [60] The NO-release properties of POP is altered based on the incorporated thiol structure, with primary thiols providing faster NO release and tertiary thiols leading to sustained NO release.…”