Amine nitrosation via NO reduction of the polyamine copper(II) complex Cu(DAC)2+

Inorganic Chemistry

Volumn 46, Issue 22, 2007, Pages 9323-9331

  Khin, Chosu ^a   Lim, Mark D ^a,b   Tsuge, Kiyoshi ^a,c   Iretskii, Alexei ^a,d   Wu, Guang ^a   Ford, Peter C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c HOKKAIDO UNIVERSITY   (Japan)

^d LAKE SUPERIOR STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; COPPER; NITROSO DERIVATIVE; POLYAMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; INFRARED SPECTROPHOTOMETRY; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROFLUOROMETRY; X RAY CRYSTALLOGRAPHY;

AMINES; COPPER; CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NITROSO COMPOUNDS; POLYAMINES; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, INFRARED;

EID: 35848934148     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic7015929     Document Type: Article

References (79)

1. (a) Ignarro, L., Ed. Nitric Oxide: Biology and Pathobiology; Academic Press: San Diego, 2000.
2. (b) Nitric Oxide and Infection; Fang, F. C., Ed.; Kluwer Academic/Plenum Publishers: New York, 1999.
3. (a) Hoshino, M.; Ozawa, K.; Seki, H.; Ford, P. C. J. Am. Chem. Soc. 1993, 115, 9568-9575.
4. (b) Miranda, K. M.; Bu, X.; Lorkovic, I. M.; Ford, P. C. Inorg. Chem. 1997 36, 4838-4848.
5. (c) Lorkovic, I. M.; Miranda, K. M.; Lee, B.; Bernhard, S.; Schoonover, J. R.; Ford, P. C. J. Am. Chem. Soc. 1998, 120, 11674-11683.
6. (d) Lorkovic, I. M.; Ford, P. C. Inorg. Chem. 1999, 38, 1467-1473.
7. (e) Lorkovic, I. M.; Ford, P. C. J. Am. Chem. Soc. 2000, 122, 6516-6517.
8. (f) Laverman, L. E.; Wanat, A.; Oszajca, J.; Stochel, G.; Ford, P. C.; van Eldik, R. J. Am. Chem. Soc. 2001, 123, 285-293.
9. (g) Laverman, L. E.; Ford, P. C. J. Am. Chem. Soc. 2001, 123, 11614-11622.
10. (h) Kurtikyan, T. S.; Martirosyan, G. G.; Lorkovic, I. M.; Ford, P. C. J. Am. Chem. Soc 2002, 124, 10124-10129.
11. (i) Lim, M. D.; Lorkovic, I. M.; Wedeking, K.; Zanella, A. W.; Works, C. F.; Massick, S. M.; Ford, P. C. J. Am. Chem. Soc. 2002, 124, 9737-9743.
12. (j) Patterson, J C.; Lorkovic, I. M.; Ford, P. C. Inorg. Chem. 2003, 42, 4902-4908.
13. (k) Ford, P. C. Pure App. Chem. 2004, 76, 335-350.
14. (l) Martirosyan, G. G.; Azizyan, A. S.; Kurtikyan, T. S.; Ford, P. C. Chem. Commun., 2004, 1488-1489.
15. (m) Kurtikyan, T. S.; Gulyan, G. M.; Martirosyan, G. G.; Lim, M. D.; Ford, P. C. J. Amer. Chem. Soc., 2005, 127, 6216-6224.
16. (a) Ford, P. C.; Fernandez, B. O.; Lim, M. D. Chem. Rev. 2005, 105, 2439-2455.
17. (b) Gwost, D.; Caulton, K. G. Inorg. Chem. 1973, 12, 2095.
18. (a) Gow, A. J.; Luchsinger, B. P.; Pawloski, J. R.; Singel, D. J.; Stamler, J. S. Proc. Nat. Acad. Sci. U.S.A. 1999, 96, 9027.
19. (b) Luchsinger, B. P.; Rich, E. N.; Gow, A. J.; Williams, E. M.; Stamler, J. S.; Singel, D. J. Proc. Nat. Acad. Sci. U.S.A. 2003, 100, 461.
20. see also (a) Gladwin, M. T.; Lancaster, J. R., Jr.; Freeman, B. A.; Schechter, A. N. Nature Med. 2003, 9, 496.
21. (b) Han, T. H.; Fukuto, J. M.; Liao, J. C. NO Bio. Chem. 2004, 10, 74.
22. (a) Feelisch, M. S.; Rassaf, T.; Manimneh, S.; Singh, N.; Byran, N. S.; Jourd'Heuil, D.; Kelm, M. FASEB J. 2002, 16, 1775.
23. (b) Bryan, N. S.; Rassaf, T.; Maloney, R. E.; Rodriguez, C. M.; Saijo, F.; Rodriguez, J. R.; Feelisch, M. Proc. Nat. Acad. Sci., U.S.A. 2004, 101, 4308.
24. (c) Rassaf, T.; Feelisch, M.; Kelm, M. Free Rad. Bio. Med. 2004, 36, 413-422.
25. (d) Bryan, N. S.; Fernandez, B. O.; Bauer, S. M.; Garcia-Saura, M. F.; Milsom, Alexandra B.; Rassaf, T.; Maloney, R. E.; Bharti, A.; Rodriguez, J.; Feelisch, M. Nat. Chem. Biol. 2005, 1, 290-297.
26. Wasser, I. M.; de Vries, S.; Moenne-Loccoz, P.; Schroeder, I.; Karlin, K. D. Chem. Rev. 2002, 102, 1201, and references therein.
27. (a) Doyle, M. P.; LePoire, D. M.; Pickering, R. A. J. Biol. Chem. 1981, 256, 12399-404.
28. (b) Huang, K. T.; Keszler, A.; Patel, N.; Patel, Rakesh, P.; Gladwin, M. T.; Kim-Shapiro, D. B.; Hogg, N. J. Biol. Chem. 2005, 280, 31126-31131.
29. (c) Huang, Z.; Shiva, S.; Kim-Shapiro, D. B.; Patel, R. P.; Ringwood, L. A.; Irby, C. E.; Huang, K. T.; Ho, C.; Hogg, N.; Schechter, A. N.; Gladwin, M. T. J. Clin. Investig. 2005, 115, 2099-2107.
30. (d) Gladwin, M. T.; et al. Nat. Chem. Biol. 2005, 1, 308-314.
31. (a) Chien, J. C. W. J. Am. Chem. Soc. 1969, 91, 2166-2168.
32. (b) Wayland, B. B.; Olson, L. W. J. Am. Chem. Soc. 1974, 96, 6037-6041.
33. Hoshino, M.; Maeda, M.; Konishi, R.; Seki, H.; Ford, P. C. J. Am. Chem. Soc. 1996, 118, 5702-5707.
34. (a) Fernandez, B. O.; Ford, P. C. J. Am. Chem. Soc. 2003, 125, 10510-10511.
35. (b) Fernandez, B. O.; Lorkovic, I. M.; Ford, P. C. Inorg. Chem. 2004, 43, 5393-5402.
36. (a) Martin, C. T.; Morse, R. H.; Kanne, R. M.; Gray, H. B.; Malmstrom, B. G.; Chan, S. I. Biochem. 1981, 20, 5147.
37. (b) Gorren, A. C. F.; de Boer, E.; Wever, R. Biochem. Biophys. Acta 1987, 916, 38-47.
38. (c) Cooper, C. E.; Torres, J.; Sharpe, M. A.; Wilson, M. T. FEBS Lett. 1997, 414, 281.
39. (d) Torres, J.; Cooper, C. E.; Wilson, M. T. J. Biol. Chem. 1998, 273, 8756.
40. (e) Torres, J.; Svistunenko, D.; Karlsson, B.; Cooper, C. E.; Wilson, M. T. J. Am. Chem. Soc. 2002, 124, 963-967.
41. (a) Tran, D.; Skelton, B. W.; White, A. H.; Laverman, L. E.; Ford, P. C. Inorg. Chem 1998, 37, 2505-2511.
42. (b) Tran, D.; Ford, P. C. Inorg. Chem. 1996,35, 2411-2412.
43. (c) Lim, M. D.; Capps, K. B.; Karpishin, T. B.; Ford, P. C. Nitric Oxide, Biol. Chem. 2005, 12, 244-251.
44. (a) Brown, G. C. Biochim. Biophys. Acta 2001, 1504, 46-57.
45. (b) Torres, J.; Sharpe, M. A.; Rosquist, A.; Cooper, C. E.; Wilson, M. T. FEBS Lett. 2000, 475, 263-266.
46. Wijma, H. J.; Canters, G. W.; de Vries, S.; Verbeet, M. P. Biochem. 2004, 43, 10467-10474.
47. Gladwin, M. T.; et al. Nat. Med. 2003, 9, 1498-1505.
48. (a) Stubauer, G.; Giuffre, A.; Sarti, P. J. Biol. Chem. 1999, 274, 28128-28133.
49. (b) Inoue, K.; Akaike, T.; Miyamoto, Y.; Okamoto, T.; Sawa, T.; Otagiri, M.; Suzuki, S.; Yoshimura, T.; Maeda, H. J. Biol. Chem. 1999, 274, 27069-27075.
50. Shiva, S.; Wang, X.; Ringwood, L. A.; Xu, X.; Yuditskaya, S.; Annavajjhala, V.; Miyajima, H.; Hogg, N.; Harris, Z. L.; Gladwin, M. T. Nat. Chem. Biol. 2006, 2, 486-493.
51. Tsuge, K.; DeRosa, F.; Lim, M. D.; Ford, P. C. J. Am. Chem. Soc. 2004, 126, 6564-6565.
52. Riklin, M.; Tran, D.; Bu, X.; Laverman, L. E.; Ford, P. C. J. Chem. Soc., Dalton Trans 2001, 1813-1819.
53. (a) Lim, M. H.; Lippard, S. J. J. Am. Chem. Soc. 2005, 127, 12170-12171.
54. (b) Lim, M. H.; Xu, D.; Lippard, S. J. Nat. Chem. Biol. 2006, 2, 375-380.
55. (c) Lim, M. H.; Wong, B. A.; Pitcock, W. H., Jr.; Mokshagundam, D.; Baik, M.-H.; Lippard, S. J. J. Am. Chem. Soc. 2006, 128, 14364-14373.
56. (d) Smith, R. C.; Tennyson, A. G.; Won, A. C.; Lippard, S. Inorg. Chem. 2006, 45, 9367-9373.
57. Xing, C.; Yu, M.; Wang, S.; Shi, Z.; Li, Y.; Zhu, D. Macromol. Rapid Commun. 2007, 28, 241-245.
58. Lim, M. D.; Lorkovic, I. M.; Ford, P. C. Methods Enzymol. 2005, 396, Part E, 3-17.
59. DeRosa, F.; Bu, X.; Ford, P. C. Inorg. Chem. 2003, 42, 4171-4178.
60. SMART Software Users Guide, Ver 5.1; Bruker Analytical X-ray Systems, Inc: Madison, WI, 1999.
61. SAINT Software Users Guide, Ver. 5.1; Bruker Analytical X-ray Systems: Madison, WI, 1999.
62. Sheldrick, G. M. SADABS, Ver. 2.05; Brucker Analytical Systems, Inc.: Madison, WI, 2001.
63. Sheldrick, G. M. SHELXTL, Ver. 6.12; Bruker Analytical X-ray Systems: Madison, WI, 2001.
64. Hehre, W. J. A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction, Inc.: Irvine, CA, 2003; p 796.
65. (a) Lee, J.; Chen, L.; West, A. H.; Richter-Addo, G. B. Chem. Rev. 2002, 102, 1019-1065.
66. (b) Chen, L.; Yi, G. B.; Wang, L. S.; Dharmawardana, U. R.; Dart, A. C.; Khan, M. A.; Richter-Aldo, G. B. Inorg. Chem. 1998, 37, 4677-4688.
67. Cooney, J. D.; Brownstein, S. K.; Simon, J. W. Can. J. Chem. 1974, 52, 3028-3036.
68. Baker, E. S.; Bushneil, J. E.; Wecksler, S.; Lim, M. D.; Manard, M. J.; Dupuis, N. F.; Ford, P. C.; Bowers, M. T. J. Am. Chem. Soc. 2005, 127, 18222-18228.
69. 34
70. (b) Taube, H.; Myers, H. J. Am. Chem. Soc. 1954, 76, 2103-2111.
71. -1.
72. Pell, S. D.; Armor, J. N. J. Am. Chem. Soc. 1973, 95, 7625-7633.
73. Ford, P. C.; Lorkovic, I. M. Chem. Rev. 2002, 102, 993-1017.
74. Palascak, M.; Shields, G. C. J. Phys. Chem. A 2004, 108, 3692-3694.
75. Shamir, D.; Zilbermann, I.; Maimon, E.; Cohen, H.; Meyerstein, D. Inorg. Chem. Commun. 2007, 10, 57-60.
76. Weichsel, W.; Maes, E. M.; Andersen, J. F.; Valenzuela, J. G.; Shokhireva, T. K.; Walker, F. A.; Montfort, W. R. Proc Nat. Acad. Sci. U.S.A. 2005, 102, 594-599.
77. Franke, A.; Stochel, G.; Suzuki, N.; Higuchi, T.; Okuzono, K.; van Eldik, R. J. Am. Chem. Soc. 2005, 127, 5360-5375.
78. 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 19%, 481 - 487.
79. Andreasen, L. V.; Lorkovic, I. M.; Richter-Addo, G. B.; Ford, P. C. Nitric Oxide 2002, 6, 228-235.