Long-term nitric oxide release and elevated temperature stability with S-nitroso-N-acetylpenicillamine (SNAP)-doped Elast-eon E2As polymer

Biomaterials

Volumn 34, Issue 28, 2013, Pages 6957-6966

  Brisbois, Elizabeth J ^a   Handa, Hitesh ^a   Major, Terry C ^a   Bartlett, Robert H ^a   Meyerhoff, Mark E ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Biocompatibility; Extracorporeal circulation; Nitric oxide; Platelets; S nitrosothiols

Indexed keywords

ELEVATED TEMPERATURE; EXTRACORPOREAL CIRCULATION; FIBRINOGEN ADSORPTION; HOMOGENEOUS COATINGS; NITRIC OXIDE RELEASE; PLATELET ACTIVATION; S-NITROSOTHIOLS; THROMBORESISTANCE;

BIOCOMPATIBILITY; BIOMEDICAL EQUIPMENT; BLOOD VESSELS; ENDOTHELIAL CELLS; FUNCTIONAL POLYMERS; NITRIC OXIDE; PHOTOCHEMICAL REACTIONS; PLATELETS; WALL FUNCTION;

PLASTIC COATINGS;

FIBRINOGEN; N ACETYL S NITROSOPENICILLAMINE; NITRIC OXIDE; POLYMER;

ANIMAL CELL; ARTICLE; BLOOD FLOW; CONTROLLED STUDY; DRUG STORAGE; NONHUMAN; PRIORITY JOURNAL; THERMOSTABILITY; THROMBOCYTE COUNT; THROMBOCYTE FUNCTION;

ANIMALS; NITRIC OXIDE; PLATELET AGGREGATION; POLYMERS; RABBITS; S-NITROSO-N-ACETYLPENICILLAMINE; TEMPERATURE;

ORYCTOLAGUS CUNICULUS;

EID: 84879462980     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2013.05.063     Document Type: Article

References (72)

1. Fang F.C. Mechanisms of nitric oxide-related antimicrobial activity. JClin Invest 1997, 99:2818-2825.
2. Luo J.-d. Chen AF. Nitric oxide: a newly discovered function on wound healing. Acta Pharmacol Sin 2005, 26:259-264.
3. Wallis J.P. Nitric oxide and blood: a review. Transfus Med 2005, 15:1-11.
4. Williams D.L.H. Achemist's view of the nitric oxide story. Org Biomol Chem 2003, 1:441-449.
5. Baek S.H., Hrabie J.A., Keefer L.K., Hou D.M., Fineberg N., Rhoades R., et al. Augmentation of intrapericardial nitric oxide level by a prolonged-release nitric oxide donor reduces luminal narrowing after porcine coronary angioplasty. Circulation 2002, 105:2779-2784.
6. Chaux A., Ruan X.M., Fishbein M.C., Ouyang Y., Kaul S., Pass J.A., et al. Perivascular delivery of a nitric oxide donor inhibits neointimal hyperplasia in vein grafts implanted in the arterial circulation. JThorac Cardiovasc Surg 1998, 115:604-614.
7. Gifford R., Batchelor M.M., Lee Y., Gokulrangan G., Meyerhoff M.E., Wilson G.S. Mediation of invivo glucose sensor inflammatory response via nitric oxide release. JBiomed Mater Res Part A 2005, 75A:755-766.
8. Mellion B.T., Ignarro L.J., Ohlstein E.H., Pontecorvo E.G., Hyman A.L., Kadowitz P.J. Evidence for the inhibitory role of guanosine 3',5'-monophosphate in ADP-induced human platelet aggregation in the presence of nitric oxide and related vasodilators. Blood 1981, 57:946-955.
9. Nablo B.J., Rothrock A.R., Schoenfisch M.H. Nitric oxide-releasing sol-gels as antibacterial coatings for orthopedic implants. Biomaterials 2005, 26:917-924.
10. Radomski M.W., Palmer R.M.J., Moncada S. Comparative pharmacology of endothelium-derived relaxing factor, nitric oxide and prostacylin in platelets. Br J Pharmacol 1987, 92:181-187.
11. Davis K.L., Martin E., Turko I.V., Murad F. Novel effects of nitric oxide. Annu Rev Pharmacol Toxicol 2001, 41:203-236.
12. Vaughn M.W. Estimation of nitric oxide production and reactionrates in tissue by use of a mathematical model. Am J Physiol Heart Circ Physiol 1998, 274:H2163.
13. Ratner B.D. The catastrophe revisited: blood compatibility in the 21st century. Biomaterials 2007, 28:5144-5147.
14. Ratner B.D., Bryant S.J. Biomaterials: where we have been and where we are going. Annu Rev Biomed Eng 2004, 6:41-75.
15. Coneski P.N., Rao K.S., Schoenfisch M.H. Degradable nitric oxide-releasing biomaterials via post-polymerization functionalization of cross-linked polyesters. Biomacromolecules 2010, 11:3208-3215.
16. Coneski P.N., Schoenfisch M.H. Synthesis of nitric oxide-releasing polyurethanes with S-nitrosothiol-containing hard and soft segments. Polym Chem 2011, 2:906-913.
17. Damodaran V.B., Reynolds M.M. Biodegradable S-nitrosothiol tethered multiblock polymer for nitric oxide delivery. JMater Chem 2011, 21:5870-5872.
18. Frost M.C., Meyerhoff M.E. Synthesis, characterization, and controlled nitric oxide release from S-nitrosothiol-derivatized fumed silica polymer filler particles. JBiomed Mater Res Part A 2005, 72A:409-419.
19. Gierke G.E., Nielsen M., Frost M.C. S-nitroso-N-acetyl-D-penicillamine covalently linked to polydimethylsiloxane (SNAP-PDMS) for use as a controlled photoinitiated nitric oxide release polymer. Sci Technol Adv Mat 2011, 12:055007.
20. Major T.C., Brant D.O., Burney C.P., Amoako K.A., Annich G.M., Meyerhoff M.E., et al. The hemocompatibility of a nitric oxide generating polymer that catalyzes S-nitrosothiol decomposition in an extracorporeal circulation model. Biomaterials 2011, 32:5957-5969.
21. Major T.C., Brant D.O., Reynolds M.M., Bartlett R.H., Meyerhoff M.E., Handa H., et al. The attenuation of platelet and monocyte activation in a rabbit model of extracorporeal circulation by a nitric oxide releasing polymer. Biomaterials 2010, 31:2736-2745.
22. Shishido S.M., Seabra A.B., Loh W., Ganzarolli de Oliveira M. Thermal and photochemical nitric oxide release from S-nitrosothiols incorporated in Pluronic F127 gel: potential uses for local and controlled nitric oxide release. Biomaterials 2003, 24:3543-3553.
23. Shishido S.M., de Oliveira M.G. Polyethylene glycol matrix reduces the rates of photochemical and thermal release of nitric oxide from S-nitroso-N-acetylcysteine. Photochem Photobiol 2000, 71:273-280.
24. Wang P.G., Xian M., Tang X.P., Wu X.J., Wen Z., Cai T.W., et al. Nitric oxide donors: chemical activities and biological applications. Chem Rev 2002, 102:1091-1134.
25. Al-Sa'doni H., Ferro A. S-nitrosothiols: a class of nitric oxide-donor drugs. Clin Sci (Lond) 2000, 98:507-520.
26. Hogg N. Biological chemistry and clinical potential of S-nitrosothiols. Free Radic Biol Med 2000, 28:1478-1486.
27. Hogg N., Singh R.J., Kalyanaraman B. The role of glutathione in the transport and catabolism of nitric oxide. FEBS Lett 1996, 382:223-228.
28. Langford E.J., Brown A.S., Wainwright R.J., Debelder A.J., Thomas M.R., Smith R.E.A., et al. Inhibition of platelet activity by S-nitrosoglutathione during coronary angioplasty. Lancet 1994, 344:1458-1460.
29. Radomski M.W., Rees D.D., Dutra A., Moncada S. S-nitroso-glutathione inhibits platelet activation invitro and invivo. Br J Pharmacol 1992, 107:745-749.
30. Salas E., Moro M.A., Askew S., Hodson H.F., Butler A.R., Radomski M.W., et al. Comparative pharmacology of analogues of S-nitroso-N-acetyl-DL-penicillamine on human platelets. Br J Pharmacol 1994, 112:1071-1076.
31. de Souza G.F.P., Yokoyama-Yasunaka J.K.U., Seabra A.B., Miguel D.C., de Oliveira M.G., Uliana S.R.B. Leishmanicidal activity of primary S-nitrosothiols against Leishmania major and Leishmania amazonensis: implications for the treatment of cutaneous leishmaniasis. Nitric Oxide-Biol Chem 2006, 15:209-216.
32. Albert J., Daleskog M., Wallen N.H. Acomparison of the antiplatelet effect of S-nitrosoglutathione in whole blood and platelet-rich plasma. Thromb Res 2001, 102:161-165.
33. Ricardo K.F.S., Shishido S.M., de Oliveira M.G., Krieger M.H. Characterization of the hypotensive effect of S-nitroso-N-acetylcysteine in normotensive and hypertensive conscious rats. Nitric Oxide-Biol Chem 2002, 7:57-66.
34. Dicks A.P., Swift H.R., Williams D.L.H., Butler A.R., AlSadoni H.H., Cox B.G. Identification of Cu+ as the effective reagent in nitric oxide formation from S-nitrosothiols (RSNO). JChem Soc Perkin Trans 1996, 2:481-487.
35. Sexton D.J., Muruganandam A., McKenney D.J., Mutus B. Visible light photochemical release of nitric oxide from S-nitrosoglutathione: potential photochemotherapeutic applications. Photochem Photobiol 1994, 59:463-467.
36. Wood P.D., Mutus B., Redmond R.W. The mechanism of photochemical release of nitric oxide from S-nitrosoglutathione. Photochem Photobiol 1996, 64:518-524.
37. Frost M.C., Meyerhoff M.E. Controlled photoinitiated release of nitric oxide from polymer films containing S-nitroso-N-acetyl-DL-penicillamine derivatized fumed silica filler. JAm Chem Soc 2004, 126:1348-1349.
38. Gordge M.P., Hothersall J.S., Neild G.H., Dutra A.A.N. Role of a copper (I)-dependent enzyme in the anti-platelet action of S-nitrosoglutathione. Br J Pharmacol 1996, 119:533-538.
39. Seabra A.B., de Souza G.F.P., da Rocha L.L., Eberlin M.N., de Oliveira M.G. S-nitrosoglutathione incorporated in poly(ethylene glycol) matrix: potential use for topical nitric oxide delivery. Nitric Oxide-Biol Chem 2004, 11:263-272.
40. Seabra A.B., de Oliveira M.G. Poly(vinyl alcohol) and poly(vinyl pyrrolidone) blended films for local nitric oxide release. Biomaterials 2004, 25:3773-3782.
41. Seabra A.B., Fitzpatrick A., Paul J., De Oliveira M.G., Weller R. Topically applied S-nitrosothiol-containing hydrogels as experimental and pharmacological nitric oxide donors in human skin. Br J Dermatol 2004, 151:977-983.
42. Amadeu T.P., Seabra A.B., De Oliveira M.G., Costa A.M.A. S-nitrosoglutathione-containing hydrogel accelerates rat cutaneous wound repair. JEur Acad Dermatol Venereol 2007, 21:629-637.
43. Stasko N.A., Fischer T.H., Schoenfisch M.H. S-nitrosothiol-modified dendrimers as nitric oxide delivery vehicles. Biomacromolecules 2008, 9:834-841.
44. Seabra A.B., da Silva R., de Oliveira M.G. Polynitrosated polyesters: preparation, characterization, and potential use for topical nitric oxide release. Biomacromolecules 2005, 6:2512-2520.
45. Seabra A.B., da Silva R., de Souza G.F.P., de Oliveira M.G. Antithrombogenic polynitrosated polyester/poly(methyl methacrylate) blend for the coating of blood-contacting surfaces. Artif Organs 2008, 32:262-267.
46. Seabra A.B., Martins D., Simoes M., da Silva R., Brocchi M., de Oliveira M.G. Antibacterial nitric oxide-releasing polyester for the coating of blood-contacting artificial materials. Artif Organs 2010, 34:E204-E214.
47. Riccio D.A., Coneski P.N., Nichols S.P., Broadnax A.D., Schoenfisch M.H. Photoinitiated nitric oxide-releasing tertiary S-nitrosothiol-modified xerogels. ACS Appl Mater Interfaces 2012, 4:796-804.
48. Riccio D.A., Dobmeier K.P., Hetrick E.M., Privett B.J., Paul H.S., Schoenfisch M.H. Nitric oxide-releasing S-nitrosothiol-modified xerogels. Biomaterials 2009, 30:4494-4502.
49. Etchenique R., Furman M., Olabe J.A. Photodelivery of nitric oxide from a nitrosothiol-derivatized surface. JAm Chem Soc 2000, 122:3967-3968.
50. Li Y., Lee P.I. Controlled nitric oxide delivery platform based on S-nitrosothiol conjugated interpolymer complexes for diabetic wound healing. Mol Pharm 2009, 7:254-266.
51. Puiu S.C., Zhou Z., White C.C., Neubauer L.J., Zhang Z., Lange L.E., et al. Metal ion-mediated nitric oxide generation from polyurethanes via covalently linked copper(II)-cyclen moieties. JBiomed Mater Res B Appl Biomater 2009, 91B:203-212.
52. Yang J., Welby J.L., Meyerhoff M.E. Generic nitric oxide (NO) generating surface by immobilizing organoselenium species via layer-by-layer assembly. Langmuir 2008, 24:10265-10272.
53. Oh B.K., Meyerhoff M.E. Spontaneous catalytic generation of nitric oxide from S-nitrosothiols at the surface of polymer films doped with lipophilic copper(II) complex. JAm Chem Soc 2003, 125:9552-9553.
54. Cozzens D., Luk A., Ojha U., Ruths M., Faust R. Surface characterization and protein interactions of segmented polyisobutylene-based thermoplastic polyurethanes. Langmuir 2011, 27:14160-14168.
55. Simmons A., Padsalgikar A.D., Ferris L.M., Poole-Warren L.A. Biostability and biological performance of a PDMS-based polyurethane for controlled drug release. Biomaterials 2008, 29:2987-2995.
56. Chipinda I., Simoyi R.H. Formation and stability of a nitric oxide donor: S-nitroso-N-acetylpenicillamine. JPhys Chem B 2006, 110:5052-5061.
57. Gunatillake P.A., Martin D.J., Meijs G.F., McCarthy S.J., Adhikari R. Designing biostable polyurethane elastomers for biomedical implants. Aust J Chem 2003, 56:545-557.
58. Megson I.L., Morton S., Greig I.R., Mazzei F.A., Field R.A., Butler A.R., et al. N-substituted analogues of S-nitroso-N-acetyl-d, l-penicillamine: chemical stability and prolonged nitric oxide mediated vasodilatation in isolated rat femoral arteries. Br J Pharmacol 1999, 126:639-648.
59. Stephens A., Watts R. The treatment of cystinuria with N-acetyl-D-penicillamine, a comparison with the results of D-penicillamine treatment. QJ Med 1971, 40:355-370.
60. Tiruppathi C. Heavy metal toxicity: drug disposition and pharmacokinetics class 2006, http://wwwuicedu/classes/pcol/pcol331/dentalpharmhandouts2006/lecture41pdf.
61. Clarckson C. Penicillamine_NAP 2012, http://tmedwebtulaneedu/pharmwiki/dokuphp/penicillamine_nap.
62. Gledhill R., Hopkins A. Chronic inorganic mercury poisoning treated with N-acetyl-D-penicillamine. Br J Ind Med 1972, 29:225-228.
63. Kark R., Poskanzer D.C., Bullock J.D., Boylen G. Mercury poisoning and its treatment with N-acetyl-d, l-penicillamine. NEngl J Med 1971, 285:10.
64. Parameshvara V. Mercury poisoning and its treatment with N-acetyl- d, l -penicillamine. Br J Ind Med 1967, 24:73-76.
65. Markowitz L., Schaumburg H.H. Successful treatment of inorganic mercury neurotoxicity with N-acetyl-penicillamine despite an adverse reaction. Neurology 1980, 30:1000-1001.
66. Srivastava P., Arif A.J., Singh C., Pandey V.C. N-acetyl-penicillamine: a protector of Plasmodium berghei induced stress organ injury in mice. Pharmacol Res 1997, 36:305-307.
67. Lin C.E., Richardson S.K., Wang W.H., Wang T.S., Garvey D.S. Preparation of functionalized tertiary thiols and nitrosothiols. Tetrahedron 2006, 62:8410-8418.
68. Rassaf T., Kleinbongard P., Preik M., Dejam A., Gharini P., Lauer T., et al. Plasma nitrosothiols contribute to the systemic vasodilator effects of intravenously applied NO - experimental and clinical study on the fate of NO in human blood. Circ Res 2002, 91:470-477.
69. McGrowder D., Ragoobirsingh D., Dasgupta T. Effects of S-nitroso-N-acetyl-penicillamine administration on glucose tolerance and plasma levels of insulin and glucagon in the dog. Nitric Oxide-Biol Chem 2001, 5:402-412.
70. Fatokun A.A., Stone T.W., Smith R.A. Prolonged exposures of cerebellar granule neurons to S-nitroso-N-acetylpenicillamine (SNAP) induce neuronal damage independently of peroxynitrite. Brain Res 2008, 1230:265-272.
71. Khalilmanesh F., Price R.G. Effect of D-penicillamine on glomerular basement membrane, urinary N-acetyl-beta-d-glucosaminidase and protein excretion in rats. Toxicology 1983, 26:325-334.
72. Zamora R., Matthys K.E., Herman A.G. The protective role of thiols against nitric oxide-mediated cytotoxicity in murine macrophage J774 cells. Eur J Pharmacol 1997, 321:87-96.