S-Nitrosothiol-modified dendrimers as nitric oxide delivery vehicles

Biomacromolecules

Volumn 9, Issue 3, 2008, Pages 834-841

  Stasko, Nathan A ^a   Fischer, Thomas H ^b   Schoenfisch, Mark H ^a  

^a University of North Carolina at Chapel Hill   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; CHARACTERIZATION; DECOMPOSITION; MACROMOLECULES; NITRIC OXIDE; SYNTHESIS (CHEMICAL);

NITRITE SOLUTIONS; POLYAMIDOAMINE; S-NITROSOTHIOL;

DENDRIMERS;

ACETYLCYSTEINE; COPPER; DENDRIMER; N ACETYLPENICILLAMINE; NITRIC OXIDE; NITRITE; POLYAMIDOAMINE; S NITROSOTHIOL; THIOL DERIVATIVE; THROMBIN; DRUG DERIVATIVE; DRUG VEHICLE; G4 S NITROSO N ACETYLCYSTEINE; G4 S NITROSO N ACETYLPENICILLAMINE; G4-S-NITROSO-N-ACETYLCYSTEINE; G4-S-NITROSO-N-ACETYLPENICILLAMINE; NITRIC OXIDE DONOR; NYLON; PAMAM G4; PAMAM-G4; PENICILLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMOLUMINESCENCE; CONTROLLED STUDY; DECOMPOSITION; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG STABILITY; DRUG SYNTHESIS; GEL PERMEATION CHROMATOGRAPHY; HUMAN; MACROMOLECULE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THROMBOCYTE AGGREGATION INHIBITION; ULTRAVIOLET SPECTROSCOPY; CHEMISTRY; DELAYED RELEASE FORMULATION; DRUG EFFECT; LIGHT; RADIATION EXPOSURE; SYNTHESIS; THROMBOCYTE AGGREGATION; VEHICLES;

ACETYLCYSTEINE; COPPER; DELAYED-ACTION PREPARATIONS; DENDRIMERS; HUMANS; LIGHT; NITRIC OXIDE; NITRIC OXIDE DONORS; NYLONS; PENICILLAMINE; PLATELET AGGREGATION; S-NITROSOTHIOLS; VEHICLES;

EID: 41949132533     PISSN: 15257797     EISSN: None     Source Type: Journal    
DOI: 10.1021/bm7011746     Document Type: Article

References (57)

1. Hogg, N. Annu. Rev. Pharmacol. Toxicol. 2002, 42, 585-600.
2. Tyurin, V. A.; Tyurina, Y. Y.; Liu, S.-Xi.; Bayir, H.; Hubel, C. A.; Kagan, V. E. Methods Enzymol. 2002, 352, 347-360.
3. Stamler, J. S. Circ. Res. 2004, 94, 414-417.
4. Al-Sa'doni, H. H.; Ferro, A. Curr. Med. Chem. 2004, 11, 2679-2690.
5. Hogg, N. Free Radical Biol. Med. 2000, 28, 1478-1486.
6. Gref, R.; Minamitake, Y.; Paracchia, M. T.; Trubetskoy, V.; Torchilin, V. P.; Langer, R. Science 1994, 263, 1600-1603.
7. Ignarro, L. J. Angew. Chem., Int. Ed. 1999, 38, 1882-1892.
8. Babich, H.; Zuckerbraun, H. L. Toxicol. in Vitro 2001, 15, 181-190.
9. Hou, Y.; Wang, J.; Andreana, P. R.; Cantauria, G.; Tarasia, S.; Sharp, L.; Braunschweiger, P. G.; Wang, P. G. Bioorg. Med. Chem. Lett. 1999, 9, 2255-2258.
10. de Souza, G. F. P.; Yokoyama-Yasunaka, J. K. U.; Seabra, A. B.; Miguel, D. C.; de Oliveira, M. G.; Uliana, S. R. B. Nitric Oxide 2006, 15, 209-216.
11. Fang, F. C. Nat. Rev. Microbiol. 2004, 2, 820-832.
12. Mannick, J. B. Proc. Am. Thorac. Soc. 2006, 3, 161-165.
13. Schapiro, J. M.; Libby, S. J.; Fang, F. C. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 8496-8501.
14. Bell, R. M.; Maddock, H. L.; Yellon, D. M. Cardiovasc. Res. 2003, 57, 405-415.
15. Konorev, E. A.; Tarpey, M. M.; Joseph, J.; Baker, J. E.; Kalyanaraman, B. J. Pharmacol. Exp. Ther. 1995, 274, 200-206.
16. Schulz, R.; Kelm, M.; Heusch, G. Cardiovasc. Res. 2004, 61, 402-413.
17. Mellion, B. T.; Ignarro, L. J.; Myers, C. B.; Ohlstein, E. H.; Ballot, B. A.; Hyman, A. L.; Kadowitz, P. J. Mol. Pharmacol. 1983, 23, 653-664.
18. Radomski, M. W.; Rees, D. D.; Dutra, A.; Moncada, S. Br. J. Pharmacol. 1992, 107, 754-749.
19. de Belder, A. J.; MacAllister, R.; Radomski, M. W.; Moncada, S.; Vallance, P. J. T. Cardiovasc. Res. 1994, 28, 691-694.
20. Radomski, M. W.; Moncada, S. Adv. Moler. Cell Biol. 1997, 18, 367-381.
21. Molloy, J.; Martin, J. F.; Baskerville, P. A:; Fraser, S. C. A.; Markus, H. S. Circulation 1998, 98, 1372-1375.
22. Salas, E.; Langford, E. J.; Marrinan, M. T.; Martin, J. F.; Moncada, S.; Debelder, A. J. Heart 1998, 80, 146-150.
23. Bohl, K. S.; West, J. L. Biomaterials 2000, 21, 2273-2278.
24. Bohl-Masters, K. S.; Lipke, E. A.; Rice, E. E. H.; Liel, M. S.; Myler, H. A.; Zygourakis, C.; Tulis, D. A.; West, J. L. J. Biomater. Sci., Polym. Ed. 2005, 16, 659-672.
25. Seabra, A. B.; da Silva, R.; de Oliveira, M. G. Biomacromolecules 2005, 6, 2512-2520.
26. Frost, M. C.; Meyerhoff, M. E. J. Biomed, Mater. Res., Pan A 2005, 72, 409-419.
27. Ewing, J. F.; Young, D. V.; Janero, D. R.; Garvey, D. S.; Grinnell, T. A. J. Pharmacol. Exp. Ther. 1997, 28, 947-954.
28. Katsumi, H.; Nishikawa, M.; Ma, S. F.; Yamashita, F.; Hashida, M. J. Pharm. Sci. 2004, 93, 2343-2352.
29. Katsumi, H.; Nishikawa, M.; Yamashita, F.; Hashida, M. J. Pharmacol. Exp. Ther. 2005, 314, 1117-1124.
30. Marks, D. S.; Vita, J. A.; Folts, J. D.; Keaney, J. F., Jr.; Welch, G. N.; Loscalzo, J. J. Clin. Invest. 1995, 96, 2630-2638.
31. Stasko, N. A.; Schoenfisch, M. H. J. Am. Chem. Soc. 2006, 128, 8265-8271.
32. Boas, U.; Heegaard, P. M. H. Chem. Soc. Rev. 2004, 33, 43-63.
33. Frechet, J. M. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3713-3725.
34. Marxer, S. M.; Rothrock, A. R.; Nablo, B. J.; Robbins, M. E.; Schoenfisch, M. H. Chem. Mater. 2003, 15, 4193-4199.
35. Beckman, J. S.; Conger, K. A. Methods1995, 7, 35-39.
36. Hou, Y.; Wang, J.-Q.; Ramirez, J.; Wang, P. G. Methods Enzymol. 1999, 301, 242-249.
37. Moynihan, H. A.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1994, 797-805.
38. Ellman, G. L. Arch. Biochem. Biophys. 1959, 82, 70-77.
39. Van Horn J. D.; Bulaj, G.; Goldenberg, D. P.; Burrows, C. J. J. Biol. Inorg. Chem. 2003, 8, 601-610.
40. Singh, R. J.; Hogg, N.; Joseph, J.; Kalyanaraman, B. J. Biol. Chem. 1996, 271, 18596-18603.
41. van Baal, I.; Malda, H.; Synowsky, S. A.; van Dongen, J. L. J.; Hackeng, T. M.; Merkx, M.; Meijer, E. W. Angew. Chem, Int. Ed. 2005, 44, 5052-5057.
42. Patel, H. M. S.; Williams, D. L. H. J. Chem. Soc., Perkin Trans. 2 1990, 37-42.
43. Askew, S. C.; Barnett, D. J.; McAninly, J.; Williams, D. L. H. J. Chem. Soc., Perkin Trans 2 1995, 741-745.
44. Bartberger, M. D.; Houk, K. N.; Powell, S. C.; Mannion, J. D.; Lo, K. Y.; Stamler, J. S.; Toone, E. J. J. Am. Chem Soc. 2000, 122, 5889-5890.
45. Williams, D. L. H. Acc. Chem. Res. 1999, 32, 869-876.
46. Dicks, A. P.; Swift, H. R.; Williams, D. L. H.; Butler, A. R.; Al-Sa'doni, H. H.; Cox, B. G. J. Chem. Soc., Perkin Trans. 2 1996, 481-487.
47. Frei, B.; England, L.; Ames, B. N. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 6377-6381.
48. Scorza, G.; Pietraforte, D.; Minetti, M. Free Radical Biol. Med. 1997, 22, 633-642.
49. Sexton, D. J.; Muruganandam, A.; McKenney, D. J.; Mutus, B. Photochem. Photobiol. 1994, 59, 463-467.
50. Lu, J.-M.; Wirttbrodt, J. M.; Wang, K.; Wen, Z.; Schlegel, H. B.; Wang, P. G.; Cheng, J.-P. J. Am. Chem. Soc. 2001, 123, 2903-2904.
51. Shishido, S. M.; de Oliveira, M. G. Photochem. Photobiol. 2000, 71, 273-280.
52. Wanstall, J. C.; Homer, K. L.; Doggrell, S. A. Curr. Vasc. Pharmacol. 2005, 3, 41-53.
53. Walsh, G. M.; Leane, D.; Moran, N.; Keyes, T. E.; Forster, R. J.; Kenny, D.; O'Neill, S. Biochemistry 2007, 46, 6429-6436.
54. Root, P.; Sliskovic, I.; Mutus, B. Biochem. J. 2004, 382, 575-580.
55. Bell, S. E.; Shah, C. M.; Gordge, M. P. Biochem. J. 2007, 403, 283-288.
56. Ghaffari, A.; Miller, C. C.; McMullin, B.; Ghahary, A. Nitric Oxide 2006, 14, 21-29.
57. Kukowska-Latallo, J. F.; Candido, K. A.; Cao, Z.; Nigavekar, S. S.; Majoros, I. J.; Thomas, T. P.; Balogh, L. P.; Khan, M.; Baker, J. R. Cancer Res. 2005, 65, 5317-5324.