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  • S-nitrosothiol-terminated poly(vinyl alcohol): Nitric oxide release and skin blood flow response.

S-nitrosothiol-terminated poly(vinyl alcohol): Nitric oxide release and skin blood flow response.

Nitric oxide : biology and chemistry (2020-03-10)
Leonardo P Giglio, Guilherme F Picheth, Kaja Borup Løvschall, Alexander N Zelikin, Marcelo G de Oliveira
ABSTRACT

Polymeric biomaterials capable of delivering nitric oxide (NO) topically can be used to enhance skin blood flow (SkBF) and accelerate wound healing. Herein, we used reversible addition-fragmentation chain transfer radical (RAFT) polymerization to synthesize the first poly(vinyl alcohol) (PVA) functionalized with terminal NO-releasing S-nitrosothiol (RSNO) groups for topical NO delivery. This strategy was based on the synthesis of a precursor amino-terminated PVA (PVA-NH2), which was next functionalized with iminothiolane yielding 4-imino-4-amino-PVA-butane-1-thiol (PVA-SH), and finally S-nitrosated yielding S-nitroso 4-imino-4-amino-PVA-butane-1-thiol (PVA-SNO). Real-time chemiluminescence NO detection showed that blended films of pure PVA with PVA-SNO with mass ratios 30:70, 50:50 and 70:30 release NO with initial rates ranging from 1 to 12 nmol g-1 min-1, and lead to a 2 to 10-fold dose-response increase in the SkBF, after topical application on the ventral forearm of volunteers. These results show that PVA-SNO is a potential platform for topical NO delivery in biomedical applications.

MATERIALS
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2-Iminothiolane hydrochloride, ≥98% (TLC), powder
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Sigma-Aldrich
N-(Bromomethyl)phthalimide, 96%
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