Formation and Stability of a Nitric Oxide Donor:  <i>S</i>-Nitroso-<i>N</i>-acetylpenicillamine

Chipinda, Itai; Simoyi, Reuben H.

doi:10.1021/jp0531107

Cited by 46 publications

(45 citation statements)

References 43 publications

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“…A modified version of a previously reported method was used to synthesize SNAP [28]. Equimolar ratios of NAP and sodium nitrite were added to a 1:1 mixture of water and methanol containing 2 M HCl and 2 M H 2 SO 4 .…”

Section: Methodsmentioning

confidence: 99%

Characterization of an S-nitroso-N-acetylpenicillamine–based nitric oxide releasing polymer from a translational perspective

Goudie

Brisbois

Pant

et al. 2016

International Journal of Polymeric Materials and Polymeric Biom

130

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Due to the role of nitric oxide (NO) in regulating a variety of biological functions in humans, numerous studies on different NO releasing/generating materials have been published over the past two decades. Although NO has been demonstrated to be a strong antimicrobial and potent antithrombotic agent, NO-releasing (NOrel) polymers have not reached the clinical setting. While increasing the concentration of the NO donor in the polymer is a common method to prolong the NO-release, this should not be at the cost of mechanical strength or biocompatibility of the original material. In this work, it was shown that the incorporation of S-nitroso-penicillamine (SNAP), an NO donor molecule, into Elast-eon E2As (a copolymer of mixed soft segments of polydimethylsiloxane and poly(hexamethylene oxide)), does not adversely impact the physical and biological attributes of the base polymer. Incorporating 10 wt % of SNAP into E2As reduces the ultimate tensile strength by only 20%. The inclusion of SNAP did not significantly affect the surface chemistry or roughness of E2As polymer. Ultraviolet radiation, ethylene oxide, and hydrogen peroxide vapor sterilization techniques retained approximately 90% of the active SNAP content, where sterilization of these materials did not affect the NO-release profile over an 18 day period. Furthermore, these NOrel materials were shown to be biocompatible with the host tissues as observed through hemocompatibility and cytotoxicity analysis. In addition, the stability of SNAP in E2As was studied under a variety of storage conditions, as they pertain to translational potential of these materials. SNAP-incorporated E2As stored at room temperature for over 6 months retained 87% of its initial SNAP content. Stored and fresh films exhibited similar NO release kinetics over an 18 day period. Combined, the results from this study suggest that SNAPdoped E2As polymer is suitable for commercial biomedical applications due to the reported physical and biological characteristics that are important for commercial and clinical success.

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Section: Methodsmentioning

confidence: 99%

Characterization of an S-nitroso-N-acetylpenicillamine–based nitric oxide releasing polymer from a translational perspective

Goudie

Brisbois

Pant

et al. 2016

International Journal of Polymeric Materials and Polymeric Biom

130

View full text Add to dashboard Cite

show abstract

“…44, 70 1M HCl and 1M H 2 SO 4 was added to an equimolar amount of NAP, methanol and sodium nitrite solution containing DI water. This reaction was stirred for 15 minutes and then cooled in an ice bath for 4 hours.…”

Section: Methodsmentioning

confidence: 99%

Enhanced antibacterial efficacy of nitric oxide releasing thermoplastic polyurethanes with antifouling hydrophilic topcoats

et al. 2017

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Surface fouling is one of the leading causes of infection associated with implants, stents, catheters, and other medical devices. The surface chemistry of medical device coatings is important in controlling and/or preventing fouling. In this study, we have shown that a combination of nitric oxide releasing hydrophobic polymer with a hydrophilic polymer topcoat can significantly reduce protein attachment and subsequently reduce bacterial adhesion as a result of the synergistic effect. Nitric oxide (NO) is a well-known potent antibacterial agent due to its adverse reactions on microbial cell components. Owing to the surface chemistry of hydrophilic polymers, they are suitable as antifouling topcoats. In this study, four biomedical grade polymers were compared for protein adhesion and NO-release behavior: CarboSil 2080A, RTV, SP60D60, and SG80A. SP60D60 was found to resist protein adsorption up to 80% when compared to the other polymers while CarboSil 2080A maintained a steady NO flux even after 24 hours (~0.50 × 10−10 mol cm−2 min−1) of soaking in buffer solution with a loss of less than 3 wt% S-nitroso-N-acetylpenicillamine (SNAP), the NO donor molecule, in the leaching analysis. Therefore, CarboSil 2080A incorporated with SNAP and topcoated with SP60D60, was tested for antibacterial efficacy after exposure to fibrinogen, an abundantly found protein in blood. The NO-releasing CarboSil 2080A with SP60D60 topcoated polymer showed a 96% reduction in Staphylococcus aureus viable cell count compared to the control samples. Hence, the study demonstrated that a hydrophilic polymer topcoat, when applied to a polymer with sustained NO release from underlying SNAP incorporated hydrophobic polymer, can reduce bacterial adhesion and be used as a highly efficient antifouling, antibacterial polymer for biomedical applications.

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“…A method reported by Chipinda et al was modified for synthesizing SNAP from NAP [64]. Briefly, sodium nitrite and NAP were added in an equimolar ratio to a 1:1 mixture of methanol and water containing 2 M H 2 SO 4 and 2 M HCl.…”

Section: Methodsmentioning

confidence: 99%

A multi-defense strategy: Enhancing bactericidal activity of a medical grade polymer with a nitric oxide donor and surface-immobilized quaternary ammonium compound

et al. 2017

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Although the use of biomedical devices in hospital-based care is inevitable, unfortunately, it is also one of the leading causes of the nosocomial infections, and thus demands development of novel antimicrobial materials for medical device fabrication. In the current study, a multi-defense mechanism against Gram-positive and Gram-negative bacteria is demonstrated by combining a NO releasing agent with a quaternary ammonium antimicrobial that can be covalently grafted to medical devices. Antibacterial polymeric com posites were fabricated by incorporating a nitric oxide (NO) donor, S-nitroso-N-acetyl-penicillamine (SNAP) in CarboSil® polymer and top coated with surface immobilized benzophenone based quaternary ammonium antimicrobial (BPAM) small molecule. The results suggest that SNAP and BPAM have a different degree of toxicity towards Gram-positive and Gram-negative bacteria, and the SNAP-BPAM combination is effective in reducing both types of adhered viable bacteria equally well. SNAP-BPAM combinations reduced the adhered viable Pseudomonas aeruginosa by 99.0% and Staphylococcus aureus by 99.98% as compared to the control CarboSil films. Agar diffusion tests demonstrate that the diffusive nature of NO kills bacteria beyond the direct point of contact which the non-leaching BPAM cannot achieve alone. This is important for potential application in biofilm eradication. The live-dead bacteria staining shows that the SNAP-BPAM combination has more attached dead bacteria (than live) as compared to the controls. The SNAP-BPAM films have increased hydrophilicity and higher NO flux as compared to the SNAP films useful for preventing blood protein and bacterial adhesion. Overall the combination of SNAP and BPAM imparts different attributes to the polymeric composite that can be used in the fabrication of antimicrobial surfaces for various medical device applications.

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Formation and Stability of a Nitric Oxide Donor: S-Nitroso-N-acetylpenicillamine

Cited by 46 publications

References 43 publications

Characterization of an S-nitroso-N-acetylpenicillamine–based nitric oxide releasing polymer from a translational perspective

Characterization of an S-nitroso-N-acetylpenicillamine–based nitric oxide releasing polymer from a translational perspective

Enhanced antibacterial efficacy of nitric oxide releasing thermoplastic polyurethanes with antifouling hydrophilic topcoats

A multi-defense strategy: Enhancing bactericidal activity of a medical grade polymer with a nitric oxide donor and surface-immobilized quaternary ammonium compound

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