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

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 (C2F5-SNAP), is incorporated within the polyvinylidene fluoride (PVDF) tubing. The synthesis, decomposition kinetics, and NO-release characteristics of the C2F5-SNAP species are described in detail. Then, using a simple solvent swelling method, we demonstrate that C2F5-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/cm2·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.

SUBMITTER: Zhou Y

PROVIDER: S-EPMC6516761 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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

Zhou Yang Y Zhang Qi Q Wu Jianfeng J Xi Chuanwu C Meyerhoff Mark E ME

Journal of materials chemistry. B 20180829 38

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 (C2F5-SNAP), is incorporated within the polyvinylidene f ...[more]

PMID: 31105961

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Project description:Nitric oxide (NO) releasing polymers have been widely applied as biomaterials for a variety of biomedical implants and devices. However, the chemical leaching of NO donors and their byproduct species is almost always observed during the application of polymers doped with NO donors, unless the donor is covalently linked to the polymer. Herein, we report the first NO releasing poly(vinylidene fluoride-co-hexafluoropropylene) (PVDF-HFP) fluorinated copolymer prepared by incorporating a fluorinated S-nitrosothiol as the NO donor. Under physiological conditions, the resulting polymeric films can release NO for 16?days. Importantly, due to both fluorine-fluorine and electrostatic charge interactions between the fluorinated NO donor and the PVDF-HFP copolymer, the total chemical leaching of the fluorinated NO donor and its disulfide product after 9?day was only 0.6% (mol%) of the initial amount of NO donor loaded into the film. These new NO release PVDF-HFP films exhibit antimicrobial and anti-biofilm activities against both Gram positive S. aureus and Gram negative P. aeruginosa strains. The NO-releasing PVDF-HFP polymer can also be coated on Teflon tubing to release NO under physiological conditions for extended time periods. This NO-releasing PVDF-HFP copolymer with greatly reduced chemical leaching could help enhance the biocompatibility and antimicrobial activity of various biomedical devices. STATEMENT OF SIGNIFICANCE: Fluoropolymers have been widely used in creating various biomedical implants and devices. However, nitric oxide (NO) release fluoropolymers have not been well studied to date. Additionally, in the application of biomaterials doped with NO donors, a significant amount of NO donors and their byproducts almost always leach into aqueous environment. We now report an NO releasing poly(vinylidene fluoride-co-hexafluoropropylene) (PVDF-HFP) fluoropolymer by incorporating a new fluorinated S-nitrosothiol. The NO release can last for 16?days under physiological conditions. The total chemical leaching was determined to be only 0.6?mol% of the initial S-nitrosothiol loaded. As expected, significant antimicrobial/anti-biofilm activities of the NO release PVDF-HFP film were observed against Gram positive S. aureus and Gram negative P. aeruginosa bacterial strains.

Dataset Information

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

Publications

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

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