S-Nitroso-N-acetylpenicillamine (SNAP) Derivatization of Peptide Primary Amines to Create Inducible Nitric Oxide Donor Biomaterials

VanWagner, Michael J.; Rhadigan, Jessica; Lancina, Michael G.; Lebovsky, Allison; Romanowicz, Genevieve E.; Holmes, Hal R.; Brunette, Margaret A.; Snyder, Katherine L.; Bostwick, Michael; Lee, Bruce P.; Frost, Megan C.; Rajachar, Rupak M.

doi:10.1021/am4017945

Cited by 17 publications

(23 citation statements)

References 62 publications

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“…The SNAP approach provides a robust procedure to functionalize both natural and synthetic peptides bearing amine residues (e.g., lysine) to form NO donors. For instance, a natural protein, fibrin, was decorated with SNAP with the formation of NO-releasing peptide and the resulting peptide can remarkably inhibit bacterial adhesion compared with natural fibrin without NO-releasing capability (Vanwagner et al, 2013). Besides peptides, natural polysaccharides and oligosaccharides could also be modified with the formation of SNO-type NO donors.…”

Section: S-nitrosothiol (Sno)-based No Polymeric No Donorsmentioning

confidence: 99%

Nitric Oxide (NO)-Releasing Macromolecules: Rational Design and Biomedical Applications

Cheng

Shen

et al. 2019

Front. Chem.

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Nitric oxide (NO) has been recognized as a ubiquitous gaseous transmitter and the therapeutic potential has nowadays received increasing interest. However, NO cannot be easily directly administered due to its high reactivity in air and high concentration-dependent physiological roles. As such, a plethora of NO donors have been developed that can reversibly store and release NO under specific conditions. To enhance the stability and modulate the NO release profiles, small molecule-based NO donors were covalently linked to polymeric scaffolds, rendering them with multifunctional integration, prolonged release durations, and optimized therapeutic outcomes. In this minireview, we highlight the recent achievements of NO-releasing macromolecules in terms of chemical design and biomedical applications. We hope that more efforts could be devoted to this emerging yet promising field.

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Section: S-nitrosothiol (Sno)-based No Polymeric No Donorsmentioning

confidence: 99%

Nitric Oxide (NO)-Releasing Macromolecules: Rational Design and Biomedical Applications

Cheng

Shen

et al. 2019

Front. Chem.

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“…Genipin-cross-linked fibrin exhibited promise in functioning as an adhesive for repairing intervertebral disc annulus while demonstrating elastic modulus in the range of native annular tissue and remained adhered to the native tissue at strains exceeding physiological levels. Most recently, fibrin gel was functionalized with nitric oxide donors for preparing biomaterials capable of controlling release of nitric oxide for promoting tissue regeneration and wound healing [ 61 , 62 ].…”

Section: Future Outlookmentioning

confidence: 99%

Fibrin Gel as an Injectable Biodegradable Scaffold and Cell Carrier for Tissue Engineering

Meng

Liu

et al. 2015

The Scientific World Journal

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257

180

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Due to the increasing needs for organ transplantation and a universal shortage of donated tissues, tissue engineering emerges as a useful approach to engineer functional tissues. Although different synthetic materials have been used to fabricate tissue engineering scaffolds, they have many limitations such as the biocompatibility concerns, the inability to support cell attachment, and undesirable degradation rate. Fibrin gel, a biopolymeric material, provides numerous advantages over synthetic materials in functioning as a tissue engineering scaffold and a cell carrier. Fibrin gel exhibits excellent biocompatibility, promotes cell attachment, and can degrade in a controllable manner. Additionally, fibrin gel mimics the natural blood-clotting process and self-assembles into a polymer network. The ability for fibrin to cure in situ has been exploited to develop injectable scaffolds for the repair of damaged cardiac and cartilage tissues. Additionally, fibrin gel has been utilized as a cell carrier to protect cells from the forces during the application and cell delivery processes while enhancing the cell viability and tissue regeneration. Here, we review the recent advancement in developing fibrin-based biomaterials for the development of injectable tissue engineering scaffold and cell carriers.

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“…The well-known NO donor, S-nitroso-N-acetyl penicillamine (SNAP), has been used to release NO through photolytic cleavage of the S-N bond 25 . For use in clinical applications, recent studies have demonstrated the potential for NO release through compressive and shear mechanisms in addition to thermal mediated pathways, presenting a more clinically relevant and viable option for the application of site specific controlled NO release 1 .…”

Section: Introductionmentioning

confidence: 99%

Development of an Injectable Nitric Oxide Releasing Poly(ethylene) Glycol-Fibrin Adhesive Hydrogel

Joseph

McCarthy

Tyo

et al. 2018

ACS Biomater. Sci. Eng.

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Fibrin microparticles were incorporated into poly(ethylene) glycol (PEG)-fibrinogen hydrogels to create an injectable, composite that could serve as a wound healing support and vehicle to deliver therapeutic factors for tissue engineering. Nitric oxide (NO), a therapeutic agent in wound healing, was loaded into fibrin microparticles by blending S-Nitroso-N-acetyl penicillamine (SNAP) with a fibrinogen solution. The incorporation of microparticles affected swelling behavior and improved tissue adhesivity of composite hydrogels. Controlled NO release was induced via photolytic and thermal activation, and modulated by weight percent of particles incorporated. These NO-releasing composites were non-cytotoxic in culture. Cells maintained morphology, viability, and proliferative character. Fibrin microparticles loaded with SNAP and incorporated into a PEG-fibrinogen matrix, creates a novel injectable composite hydrogel that offers improved tissue adhesivity and inducible NO-release for use as a regenerative support for wound healing and tissue engineering applications.

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S-Nitroso-N-acetylpenicillamine (SNAP) Derivatization of Peptide Primary Amines to Create Inducible Nitric Oxide Donor Biomaterials

Cited by 17 publications

References 62 publications

Nitric Oxide (NO)-Releasing Macromolecules: Rational Design and Biomedical Applications

Nitric Oxide (NO)-Releasing Macromolecules: Rational Design and Biomedical Applications

Fibrin Gel as an Injectable Biodegradable Scaffold and Cell Carrier for Tissue Engineering

Development of an Injectable Nitric Oxide Releasing Poly(ethylene) Glycol-Fibrin Adhesive Hydrogel

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