Synthesis and Characterization of a Fluorinated S-Nitrosothiol as the Nitric Oxide Donor for Fluoropolymer-Based Biomedical Device Applications

合成和表征氟化S-亚硝基硫醇作为一氧化氮供体在氟聚合物基生物医学器件应用中的性能

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Abstract

Fluorinated polymers are widely used as biomaterials in various biomedical implant and device applications. However, thrombogenicity, surface-induced inflammation, and risk of microbial infection remain key issues that can limit their use. In this work, we describe the first nitric oxide (NO) releasing fluorinated polymer, in which a new fluorinated NO donor, S-nitroso-N-pentafluoropropionylpenicillamine (C(2)F(5)-SNAP), is incorporated within the polyvinylidene fluoride (PVDF) tubing. The synthesis, decomposition kinetics, and NO-release characteristics of the C(2)F(5)-SNAP species are described in detail. Then, using a simple solvent swelling method, we demonstrate that C(2)F(5)-SNAP can readily be doped into PVDF tubing. The resulting tubing can release NO for 11 days under physiological conditions, with an NO flux > 0.5 × 10(-10) mol/cm(2)·min over the first 7 days. Due to fluorous-fluorous interactions, the leaching of the fluorinated NO donor and its decomposed products is shown to be very low (less than 5 nmol/mg, total). Further, the new NO-releasing PVDF tubing exhibits significant antimicrobial activity (compared to undoped PVDF tubing) against both gram positive and negative S. aureus and P. aeruginosa bacterial strains over a 7 d test period. This new NO-releasing fluorinated polymer is likely to have the potential to improve the biocompatibility and antimicrobial activity of various biomedical devices.

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