Nitric oxide-releasing hydrophobic polymers: Preparation, characterization, and potential biomedical applications

Free Radical Biology and Medicine

Volumn 37, Issue 7, 2004, Pages 926-936

  Reynolds, Melissa M ^a   Frost, Megan C ^a   Meyerhoff, Mark E ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Biocompatibility; Controlled release; Diazeniumdiolates; Free radicals; Nitric oxide; Nitrosothiols; Polymers; Thromboresistant

Indexed keywords

NITRIC OXIDE; NITRIC OXIDE DONOR; POLYMER; POLYMETHACRYLIC ACID; POLYURETHAN; POLYVINYLCHLORIDE; SILASTIC; SILICON DIOXIDE; TITANIUM DIOXIDE;

CATHETER; CHEMICAL STRUCTURE; DEVICE; DISPERSION; DOPING; EXTRACORPOREAL CIRCULATION; HYDROPHOBICITY; NONHUMAN; ORGAN TRANSPLANTATION; PRIORITY JOURNAL; REVIEW; SENSOR; STENT; SYNTHESIS; THROMBOCYTE ACTIVATION; THROMBOCYTE ADHESION;

ANIMALS; BLOOD VESSELS; HUMANS; HYDROPHOBICITY; NITRIC OXIDE; NITRIC OXIDE DONORS; POLYMERS;

ANIMALIA;

EID: 4444328035     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2004.06.019     Document Type: Review

References (43)

1. R.W. Coleman Mechanisms of thrombus formation and dissolution Cardiovasc. Pathol. 2 1993 23S 31S
2. P.W. Majerus, G.J. Bronze, J.P. Miletich, and D.M. Tollefsen Anticoagulant, thrombolytic and antiplatelet drugs The Pharmacological Basis of Therapeutics 1990 Pergamon Press New York 1311 1331
3. S. Moncada, M.W. Radomski, and R.M.J. Palmer Endothelium-derived releasing factor: identification as nitric oxide and role in the control of vascular tone and platelet function Biochem. Pharmacol. 37 1988 2495 2501
4. S. Moncada, E.A. Higgs, H.F. Hodson, R.G. Knowles, P. Lopez-Jaramillo, T. McCall, R.M.J. Palmer, M.W. Radomski, D.D. Rees, and R. Schulz The l-arginine: nitric oxide pathway Cardiovasc. Pharmacol. 17 1991 S1 S9
5. M.A. Marletta, M.A. Tayeh, and J.M. Hevel Unraveling the biological significance of nitric oxide BioFactors 2 1990 219 225
6. R.F. Furchgott Endothelium-derived relaxing factor: discovery, early studies and identification as nitric oxide Biosci. Rep. 19 1998 235 251
7. A. Gries, C. Bode, K. Peter, A. Herr, H. Bohrer, J. Motsch, and E. Martin Inhaled nitric oxide inhibits human platelet aggregation, p-selectin expression, and fibrinogen binding in vitro and in vivo Circulation 97 1998 1481 1487
8. J.G. Diodati, A.A. Quyyumi, N. Hussain, and L.K. Keefer Complexes of nitric oxide with nucleophiles as agents for the controlled biological release of nitric oxide: antiplatelet effect Thromb. Haemostasis 70 1993 654 658
9. I. Fleming, and R. Busse Control and consequences of endothelial nitric oxide formation Adv. Pharmacol. 34 1995 187 206
10. M.W. Vaughn, L. Kuo, and J.C. Liao Estimation of nitric oxide production and reaction rates in tissue by use of a mathematical model Am. J. Physiol. 274 1998 H2163 H2167
11. M.K. Radomski, R.M. Palmer, and S. Moncada The role of nitric oxide and cGMP in platelet-adhesion to the vascular endothelium Biochem. Biophys. Res. Commun. 148 1987 1482 1485
12. M.W. Vaughn, L. Kuo, and J.C. Liao Effective diffusion distance of nitric oxide in the microcirculation Am. J. Physiol. 274 1998 H1705 H1714
13. S. Goldstein, and G. Czapski Kinetics of nitric oxide autoxidation in aqueous solution in the absence and presence of various reductants: the nature of the oxidizing intermediates J. Am. Chem. Soc. 117 1995 12078 12084
14. M.C. Frost, and M.E. Meyerhoff Implantable chemical sensors for real-time clinical monitoring: progress and challenges Curr. Opin. Chem. Biol. 6 2002 633 641
15. M. Telting-Diaz, M.E. Collison, and M.E. Meyerhoff Simplified dual lumen catheter design for simultaneous potentiometric monitoring of carbon dioxide and pH Anal. Chem. 66 1994 576 583
16. R.S. Drago, and F.E. Paulik The reaction of nitrogen(II) oxide with diethylamine J. Am. Chem. Soc. 82 1960 96 98
17. R.S. Drago, and B.R. Karstetter The reaction of nitrogen(II) oxide with various primary and secondary amines J. Am. Chem. Soc. 83 1961 1819 1822
18. R.S. Drago, R.O. Ragsdale, and D.P. Eyman A mechanism for the reaction of diethylamine with nitric oxide J. Am. Chem. Soc. 83 1961 4337 4339
19. R.S. Drago Reactions of nitrogen(II) oxide Adv. Chem. Ser. 1962 143 149
20. R.O. Ragsdale, B.R. Karstetter, and R.S. Drago Decomposition of the adducts of diethylamine and isopropylamine with nitrogen(II) oxide Inorg. Chem. 4 1965 420 422
21. J.A. Hrabie, and L.K. Keefer New nitric oxide-releasing zwitterions derived from polyamines J. Org. Chem. 58 1993 1472 1476
22. C.M. Maragos, D. Morley, D.A. Wink, T.M. Dunams, J.E. Saavedra, A. Hoffman, A.A. Bove, L. Isaac, J.A. Hrabie, and L.K. Keefer Complexes of NO with nucleophiles as agents for the controlled biological release of nitric oxide: vasorelaxant effects J. Med. Chem. 34 1991 3242 3247
23. K.M. Davies, D.A. Wink, J.E. Saavedra, and L.K. Keefer Chemistry of diazeniumdiolates: 2. Kinetics and mechanism of dissociation to nitric oxide in aqueous solution J. Am. Chem. Soc. 123 2001 5473 5481
24. - group J. Med. Chem. 39 1996 1148 1156
25. K.A. Mowery, M.H. Schoenfisch, J.E. Saavedra, L.K. Keefer, and M.E. Meyerhoff Preparation and characterization of hydrophobic polymeric films that are thromboresistant via nitric oxide release Biomaterials 21 2000 9 21
26. M.H. Schoenfisch, K.A. Mowery, M.V. Rader, N. Baliga, J.A. Wahr, and M.E. Meyerhoff Improving the thromboresistivity of chemical sensors via nitric oxide release: fabrication and in vivo evaluation of NO-releasing oxygen-sensing catheters Anal. Chem. 72 2000 1119 1126
27. G.M. Annich, J.P. Meinhardt, K.A. Mowery, B.A. Ashton, S.I. Merz, R.B. Hirschl, M.E. Meyerhoff, and R.H. Bartlett Reduced platelet activation and thrombosis in extracorporeal circuits coated with nitric oxide release polymers Crit. Care Med. 28 2000 915 920
28. W. Lijinsky Chemical structure of nitrosoamines related to carcinogenesis R.N. Loeppky C.J. Michejda Nitrosoamines and related N-nitrso compounds 1994 Am. Chem. Soc. Washington, D.C. 250 266
29. M.M. Batchelor, S.L. Reoma, P.S. Fleser, V.K. Nuthakki, R.E. Callahan, C.J. Shanley, J.K. Politis, J. Elmore, S.I. Merz, and M.E. Meyerhoff More lipophilic dialkyldiamine-based diazeniumdiolates: synthesis, characterization, and application in preparing thromboresistant nitric oxide release polymeric coatings J. Med. Chem. 46 2003 5153 5161
30. M.C. Frost, M.M. Batchelor, Y.M. Lee, H.P. Zhang, Y.J. Kang, B.K. Oh, G.S. Wilson, R. Gifford, S.M. Rudich, and M.E. Meyerhoff Preparation and characterization of implantable sensors with nitric oxide release coatings Microchem. J. 74 2003 277 288
31. Fleser, P. S.; Nuthakki, V. K.; Malinzak, L. E.; Callahan, R. E.; Seumour, M. L.; Reynolds, M. M.; Merz, S. I.; Meyerhoff, M. E.; Bendick, P. J.; Zelenock, G. B.; Shanley, C. J. Nitric-oxide releasing biopolymers inhibit thrombus formation in a sheep model of arteriovenous bridge grafts. Submitted for publication.
32. S. Gagliardi, V. Arrighi, R. Ferguson, and M.T.F. Telling Restricted dynamics in polymer-filler systems Physica B 301 2001 110 114
33. A. Karim, D.-W. Liu, J.F. Douglas, A.I. Nakatani, and E.J. Amis Modification of the phase stability of polymer blends by fillers Polymer 41 2000 8455 8458
34. J. Wen, and D. Bryant Fumed silica controls rheology of adhesives and sealants Adhesives Sealants Ind. August 1999
35. H. Zhang, G.M. Annich, J. Miskulin, K. Stankiewicz, K. Osterholzer, S.I. Merz, R.H. Bartlett, and M.E. Meyerhoff Nitric oxide-releasing fumed silica particles: synthesis, characterization, and biomedical applications J. Am. Chem. Soc. 125 2003 5015 5024
36. V. Hample, C.L. Wasters, and S.L. Archer Determination of nitric oxide by the chemiluminescence reaction with ozone M. Feelish J.S. Stamler Methods in nitric oxide research 1996 Wiley Chichester 309 318
37. M.C. Frost, and M.E. Meyerhoff Controlled photoinitiated release of nitric oxide from polymer films containing S-nitroso-N-acetyl-dl-penicillamine derivatized fumed silica filler J. Am. Chem. Soc. 126 2004 1348 1349
38. D.L.H. Williams The chemistry of nitrosothiols Acc. Chem. Res. 32 1999 869 876
39. J.E. Saavedra, M.N. Booth, J.A. Hrabie, K.M. Davies, and L.K. Keefer Piperazine as a linker for incorporating the nitric oxide-releasing diazeniumdiolate group into other biomedically relevant functional molecules J. Org. Chem. 64 1999 5124 5131
40. H. Zhang, G.M. Annich, J. Miskulin, K. Osterholzer, S.I. Merz, R.H. Bartlett, and M.E. Meyerhoff Nitric oxide releasing silicone rubbers with improved blood compatibility: preparation, characterization and in vivo evaluation Biomaterials 23 2002 1485 1494
41. M.C. Frost, S.M. Rudich, H. Zhang, M.A. Maraschio, and M.E. Meyerhoff In vivo biocompatibility and analytical performance of intravascular amperometric oxygen sensors prepared with improved nitric oxide-releasing silicone tubber coating Anal. Chem. 74 2002 5942 5947
42. P.G. Parzuchowski, M.C. Frost, and M.E. Meyerhoff Synthesis and characterization of polymethacrylate-based nitric oxide donors J. Am. Chem. Soc. 124 2002 12182 12191
43. B.K. Oh, and M.E. Meyerhoff Spontaneous catalytic generation of nitric oxide from S-nitrosothiols at the surface of polymer films doped with lipophilic copper(II) complex J. Am. Chem. Soc. 125 2003 9552 9553