Synthesis and Characterization of Controlled Nitric Oxide Release from -Nitroso--Acetyl-d-Penicillamine Covalently Linked to Polyvinyl Chloride (SNAP-PVC)

Overview

Journal Bioengineering (Basel)

Date 2018 Sep 8

PMID 30189614

Citations 8

Authors

Sean P Hopkins

Megan C Frost

Affiliations

Soon will be listed here.

Abstract

Polyvinyl chloride (PVC) is one of the most widely used polymers in medicine but has very poor biocompatibility when in contact with tissue or blood. To increase biocompatibility, controlled release of nitric oxide (NO) can be utilized to mitigate and reduce the inflammatory response. A synthetic route is described where PVC is aminated to a specified degree and then further modified by covalently linking -nitroso--acetyl-d-penicillamine (SNAP) groups to the free primary amine sites to create a nitric oxide releasing polymer (SNAP-PVC). Controllable release of NO from SNAP-PVC is described using photoinitiation from light emitting diodes (LEDs). Ion-mediated NO release is also demonstrated as another pathway to provide a passive mechanism for NO delivery. The large range of NO fluxes obtained from the SNAP-PVC films indicate many potential uses in mediating unwanted inflammatory response in blood- and tissue-contacting devices and as a tool for delivering precise amounts of NO in vitro.

Citing Articles

Combination of melatonin-delivered endothelial progenitor cells with S-nitroso-N-acetyl-DL-penicillamine for improving critical limb ischemia in the rat.

Yeh J, Yip H, Shao P, Chiang J, Wu S, Sung P Am J Transl Res. 2024; 16(9):5020-5037.

PMID: 39398551 PMC: 11470315. DOI: 10.62347/OCFT1003.

Wearable nitric oxide-releasing antibacterial insert for preventing device-associated infections.

Chug M, Sapkota A, Garren M, Brisbois E J Control Release. 2024; 375():667-680.

PMID: 39288891 PMC: 11748947. DOI: 10.1016/j.jconrel.2024.09.027.

Antimicrobial properties of hindered amine light stabilizers in polymer coating materials and their mechanism of action.

Costa T, Sampaio-Marques B, Neves N, Aguilar H, Fraga A Front Bioeng Biotechnol. 2024; 12:1390513.

PMID: 38978720 PMC: 11229053. DOI: 10.3389/fbioe.2024.1390513.

Chemical Modification of Tiopronin for Dual Management of Cystinuria and Associated Bacterial Infections.

Kumar A, Estes Bright L, Garren M, Manuel J, Shome A, Handa H ACS Appl Mater Interfaces. 2023; 15(37):43332-43344.

PMID: 37671841 PMC: 10520916. DOI: 10.1021/acsami.3c07160.

Smartphone compatible nitric oxide releasing insert to prevent catheter-associated infections.

Chug M, Brisbois E J Control Release. 2022; 349:227-240.

PMID: 35777483 PMC: 9680949. DOI: 10.1016/j.jconrel.2022.06.043.

References

Stasko N, Fischer T, Schoenfisch M . S-nitrosothiol-modified dendrimers as nitric oxide delivery vehicles. Biomacromolecules. 2008; 9(3):834-41. PMC: 3564213. DOI: 10.1021/bm7011746. View

Zhang H, Annich G, Miskulin J, Osterholzer K, Merz S, Bartlett R . Nitric oxide releasing silicone rubbers with improved blood compatibility: preparation, characterization, and in vivo evaluation. Biomaterials. 2002; 23(6):1485-94. DOI: 10.1016/s0142-9612(01)00274-5. View

Frost M, Reynolds M, Meyerhoff M . Polymers incorporating nitric oxide releasing/generating substances for improved biocompatibility of blood-contacting medical devices. Biomaterials. 2004; 26(14):1685-93. DOI: 10.1016/j.biomaterials.2004.06.006. View

Liu J, Hsieh Y, Wiesler D, Novotny M . Design of 3-(4-carboxybenzoyl)-2-quinolinecarboxaldehyde as a reagent for ultrasensitive determination of primary amines by capillary electrophoresis using laser fluorescence detection. Anal Chem. 1991; 63(5):408-12. DOI: 10.1021/ac00005a004. View

Pant J, Gao J, Goudie M, Hopkins S, Locklin J, Handa H . A multi-defense strategy: Enhancing bactericidal activity of a medical grade polymer with a nitric oxide donor and surface-immobilized quaternary ammonium compound. Acta Biomater. 2017; 58:421-431. PMC: 5685542. DOI: 10.1016/j.actbio.2017.05.061. View

Gierke G, Nielsen M, Frost M . S-Nitroso--acetyl-D-penicillamine covalently linked to polydimethylsiloxane (SNAP-PDMS) for use as a controlled photoinitiated nitric oxide release polymer. Sci Technol Adv Mater. 2016; 12(5):055007. PMC: 5074439. DOI: 10.1088/1468-6996/12/5/055007. View

Starrett M, Nielsen M, Smeenge D, Romanowicz G, Frost M . Wireless platform for controlled nitric oxide releasing optical fibers for mediating biological response to implanted devices. Nitric Oxide. 2012; 27(4):228-34. DOI: 10.1016/j.niox.2012.08.074. View

Mellion B, Ignarro L, Myers C, Ohlstein E, Ballot B, HYMAN A . Inhibition of human platelet aggregation by S-nitrosothiols. Heme-dependent activation of soluble guanylate cyclase and stimulation of cyclic GMP accumulation. Mol Pharmacol. 1983; 23(3):653-64. View

He W, Frost M . Direct measurement of actual levels of nitric oxide (NO) in cell culture conditions using soluble NO donors. Redox Biol. 2016; 9:1-14. PMC: 4899081. DOI: 10.1016/j.redox.2016.05.002. View

10.

Chen C, Hanson S, Keefer L, Saavedra J, Davies K, Hutsell T . Boundary layer infusion of nitric oxide reduces early smooth muscle cell proliferation in the endarterectomized canine artery. J Surg Res. 1997; 67(1):26-32. DOI: 10.1006/jsre.1996.4915. View

11.

Radomski M, Palmer R, Moncada S . An L-arginine/nitric oxide pathway present in human platelets regulates aggregation. Proc Natl Acad Sci U S A. 1990; 87(13):5193-7. PMC: 54288. DOI: 10.1073/pnas.87.13.5193. View

12.

MacMicking J, Xie Q, Nathan C . Nitric oxide and macrophage function. Annu Rev Immunol. 1997; 15:323-50. DOI: 10.1146/annurev.immunol.15.1.323. View

13.

Brisbois E, Handa H, Major T, Bartlett R, Meyerhoff M . Long-term nitric oxide release and elevated temperature stability with S-nitroso-N-acetylpenicillamine (SNAP)-doped Elast-eon E2As polymer. Biomaterials. 2013; 34(28):6957-66. PMC: 3729938. DOI: 10.1016/j.biomaterials.2013.05.063. View

14.

Lakshmi S, Jayakrishnan A . Migration resistant, blood-compatible plasticized polyvinyl chloride for medical and related applications. Artif Organs. 1998; 22(3):222-9. DOI: 10.1046/j.1525-1594.1998.06124.x. View

15.

Nablo B, Rothrock A, Schoenfisch M . Nitric oxide-releasing sol-gels as antibacterial coatings for orthopedic implants. Biomaterials. 2004; 26(8):917-24. DOI: 10.1016/j.biomaterials.2004.03.031. View

16.

Ellman G . Tissue sulfhydryl groups. Arch Biochem Biophys. 1959; 82(1):70-7. DOI: 10.1016/0003-9861(59)90090-6. View

17.

Kolluru G, Sinha S, Majumder S, Muley A, Siamwala J, Gupta R . Shear stress promotes nitric oxide production in endothelial cells by sub-cellular delocalization of eNOS: A basis for shear stress mediated angiogenesis. Nitric Oxide. 2010; 22(4):304-15. DOI: 10.1016/j.niox.2010.02.004. View

18.

Blass C, Jones C, Courtney J . Biomaterials for blood tubing: the application of plasticised poly(vinyl chloride). Int J Artif Organs. 1992; 15(4):200-3. View

19.

Lu Y, Slomberg D, Schoenfisch M . Nitric oxide-releasing chitosan oligosaccharides as antibacterial agents. Biomaterials. 2013; 35(5):1716-24. PMC: 3889664. DOI: 10.1016/j.biomaterials.2013.11.015. View

20.

Brisbois E, Major T, Goudie M, Bartlett R, Meyerhoff M, Handa H . Improved hemocompatibility of silicone rubber extracorporeal tubing via solvent swelling-impregnation of S-nitroso-N-acetylpenicillamine (SNAP) and evaluation in rabbit thrombogenicity model. Acta Biomater. 2016; 37:111-9. PMC: 4870167. DOI: 10.1016/j.actbio.2016.04.025. View