4-Aryl-1,3,2-oxathiazolylium-5-olates as pH-controlled NO-donors: The next generation of S-nitrosothiols

Journal of the American Chemical Society

Volumn 129, Issue 17, 2007, Pages 5503-5514

  Lu, Dongning ^a   Nadas, Janos ^a   Zhang, Guisheng ^c   Johnson, Wesley ^b   Zweier, Jay L ^b   Cardounel, Arturo J ^b   Villamena, Frederick A ^b   Wang, Peng George ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c HENAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLOXATHIAZOLYLIUMOLATES; GLUTHATHIONE; NITROSOTHIOLS;

ALCOHOLS; BIOLOGICAL SYSTEMS; DENSITY FUNCTIONAL THEORY; PARAMAGNETIC RESONANCE; RING OPENING POLYMERIZATION; SUBSTITUTION REACTIONS;

NITRIC OXIDE;

4 (4 CHLOROPHENYL) 1,3,2 OXATHIAZOLYLIUM 5 OLATE; 4 (4 METHOXYPHENYL) 1,3,2 OXATHIAZOLYLIUM 5 OLATE; 4 (4 TRIFLUOROMETHYLPHENYL) 1,3,2 OXATHIAZOLYLIUM 5 OLATE; 4 PHENYL 1,3,2 OXATHIAZOLYLIUM 5 OLATE; 5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ASCORBIC ACID; CARBAMIC ACID DERIVATIVE; GLUTATHIONE; IRON N METHYL DEXTRO GLUCAMINE DITHIOCARBAMATE; NITRIC OXIDE; S NITROSOTHIOL; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; BIOLOGY; CATALYSIS; DECOMPOSITION; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; PH; RING OPENING; SPIN TRAPPING; ULTRAVIOLET SPECTROPHOTOMETRY; VASODILATATION;

ANIMALS; CHEMISTRY, PHYSICAL; COMPUTATIONAL BIOLOGY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; MODELS, MOLECULAR; NITRIC OXIDE; NITRIC OXIDE DONORS; OXAZOLES; RATS; S-NITROSOTHIOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS; THIAZOLES; VASODILATOR AGENTS;

EID: 34247849251     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0682226     Document Type: Article

References (85)

1. Ignarro, L. J. Nitric Oxide 1996, 111.
2. Ignarro, L. J., Murad, F., Eds. Nitric Oxide: Biochemistry, Molecular Biology, and Therapeutic Implications. Adv. Pharmacol. 1995, 34, 530.
3. Lancaster, J., Jr., Ed. Nitric Oxide: Principles and Actions; 1996; p 355.
4. Ignarro, L. J., Ed. Nitric Oxide: Biology and Pathobiology; 2000; p 1003.
5. Foster, M. W.; Pawloski, J. R.; Singel, D. J.; Stamler, J. S. Hypertension 2004, 45, 15.
6. Zhang, Y.; Hogg, N. Am. J. Physiol. 2004, 287, L467.
7. Lipton, S. A.; Choi, Y. B.; Pan, Z. H.; Lei, S. Z.; Chen, H. S.; Sucher, N. J.; Loscalzo, J.; Singel, D. J.; Stamler, J. S. Nature 1993, 364, 626.
8. Lander, H. M.; Ogiste, J. S.; Pearce, S. F.; Levi, R.; Novogrodsky, A. J. Biol. Chem. 1995, 270, 7017.
9. Caselli, A.; Camici, G.; Manao, G.; Moneti, G.; Pazzagli, L.; Cappugi, G.; Ramponi, G. J. Biol. Chem. 1994, 269, 24878.
10. Gopalakrishna, R.; Chen, Z. H.; Gundimeda, U. J. Biol. Chem. 1993, 268, 27180.
11. Mohr, S.; Stamler, J. S.; Brune, B. J. Biol. Chem. 1996, 271, 4209.
12. Boschi, D.; Tron, G. C.; Di Stilo, A.; Fruttero, R.; Gasco, A.; Poggesi, E.; Motta, G.; Leonardi, A. J. Med. Chem. 2003, 46, 3762.
13. Cai, T. B.; Lu, D.; Landerholm, M.; Wang, P. G. Org. Lett. 2004, 6, 4203.
14. Cai, T. B.; Lu, D.; Tang, X.; Zhang, Y.; Landerholm, M.; Wang, P. G. J. Org. Chem. 2005, 70, 3518.
15. Huang, J.; Kim-Shapiro, D. B.; King, S. B. J. Med. Chem. 2004, 47, 3495.
16. Huang, J.; Zou, Z.; Kim-Shapiro, D. B.; Ballas, S. K.; King, S. B. J. Med. Chem. 2003, 46, 3748.
17. Jia, Q.; Janczuk, A. J.; Cai, T.; Xian, M.; Wen, Z.; Wang, P. G. Expert Opin. Ther. Pat. 2002, 12, 819.
18. Lazzarato, L.; Rolando, B.; Lolli, M. L.; Tron, G. C.; Fruttero, R.; Gasco, A.; Deleide, G.; Guenther, H. L. J. Med. Chem. 2005, 48, 1322.
19. Sorba, G.; Galli, U.; Cena, C.; Fruttero, R.; Gasco, A.; Morini, G.; Adami, M.; Coruzzi, G.; Brenciaglia, M. I.; Dubini, F. ChemBioChem 2003, 4, 899.
20. Xian, M.; Fujiwara, N.; Wen, Z.; Cai, T.; Kazuma, S.; Janczuk, A. J.; Tang, X.; Telyatnikov, V. V.; Zhang, Y.; Chen, X.; Miyamoto, Y.; Taniguchi, N.; Wang, P. G. Bioorg. Med. Chem. 2002, 10, 3049.
21. Terwel, D.; Nieland, L. J. M.; Schutte, B.; Reutelingsperger, C. P. M.; Ramaekers, F. C. S.; Steinbusch, H. W. M. Eur. J. Pharmacol. 2000, 400, 19.
22. Bouton, C.; Raveau, M.; Drapier, J. C. J. Biol. Chem. 1996, 271, 2300.
23. Kaye, D. M.; Wiviott, S. D.; Kobzik, L.; Kelly, R. A.; Smith, T. W. Am. J. Physiol. 1997, 272, H875.
24. Luscher, T. F.; Raij, L.; Vanhoutte, P. M. Hypertension 1987, 9, 157.
25. Lefer, A. M.; Sedar, A. W. Pharmacol. Res. 1991, 23, 1.
26. Drexler, H.; Hayoz, D.; Munzel, T.; Hornig, B.; Just, H.; Brunner, H. R.; Zelis, R. Am. J. Cardiol. 1992, 69, 1596.
27. Bizzozero, O. A.; DeJesus, G.; Howard, T. A. Neurochem. Res. 2004, 29, 1675.
28. Zhang, Y.; Hogg, N. Biennial Meeting of the Society for Free Radical Research International, 12th, Buenos Aires, Argentina, May 5-9, 2004; p 167.
29. Mathews, W. R.; Kerr, S. W. J. Pharmacol. Exp. Ther. 1993, 267, 1529.
30. Wang, K.; Zhang, W.; Xian, M.; Hou, Y. C.; Chen, X. C.; Cheng, J. P.; Wang, P. G. Curr. Med. Chem. 2000, 7, 821.
31. Hou, Y.; Wang, J.; Andreana, P. R.; Caaantauria, G.; Tarasia, S.; Sharp L.; Braunschweiger, P. G.; Wang, P. G. Bioorg. Med. Chem. Lett. 1999, 9, 2255.
32. Butler, A. R.; Field, R. A.; Greig, I. R.; Flitney, F. W.; Bisland, S. K. Khan, F.; Belch, J. J. F. Nitric Oxide 1997, 1, 211.
33. Butler, A. R.; Al-Sa'doni, H. H.; Megson, I. L.; Flitney, F. W. Nitric Oxide 1998, 2, 193.
34. Chen, X.; Wen, Z.; Xian, M.; Wang, K.; Ramachandran, N.; Tang, X.; Schlegel, H. B.; Mutus, B.; Wang, P. G. J. Org. Chem. 2001, 66, 6064.
35. Bartberger, M. D.; Mannion, J. D.; Powell, S. C.; Stamler, J. S.; Houk, K. N.; Toone, E. J. J. Am. Chem. Soc. 2001, 123, 8868.
36. Stamler, J. S.; Toone, E. J. Curr. Opin. Chem. Biol. 2002, 6, 779.
37. Roy, B.; du Moulinet d'Hardemare, A.; Fontecave, M. J. Org. Chem. 1994, 59, 7019.
38. Carnahan, G. E.; Lenhert, P. G.; Ravichandran, R. Acta Crystallogr., Sect. B 1978, B34, 2645.
39. Zhang, Y.; Hogg, N. Free Radical Biol. Med. 2004, 36, 947.
40. Gotthardt, H. Chem. Ber. 1972, 105, 2008.
41. Gotthardt, H. Tetrahedron Lett. 1971, 17, 1277.
42. Gotthardt, H. Chem. Ber. 1972, 105, 196.
43. Gotthardt, H. Tetrahedron Lett. 1971, 17, 1281.
44. Gotthardt, H.; Reiter, F.; Kromer, C. Liebigs Ann. Chem. 1981, 6, 1025.
45. Bruce, J. M.; Sutcliffe, F. K. J. Chem. Soc. Abstr. 1957, 4789.
46. Gotthardt, H. Chem. Ber. 1972, 105, 188.
47. Li, H.; Cui, H.; Liu, X.; Zweier, J. L. J. Biol. Chem. 2005, 280, 16594.
48. Mordvintcev, P.; Muelsch, A.; Busse, R.; Vanin, A. Anal. Biochem. 1991, 199, 142.
49. Xia, Y.; Cardounel, A. J.; Vanin, A. F.; Zweier, J. L. Free Radical Biol. Med. 2000, 29, 793.
50. Wang, P. G.; Xian, M.; Tang, X.; Wu, X.; Wen, Z.; Cai, T.; Janczuk, A. J. Chem. Rev. 2002, 102, 1091.
51. Villamena, F. A.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2003, 107, 4407.
52. Davies, M. J.; Forni, L. G.; Shuter, S. L. Chem. Biol. Interact. 1987, 61, 177.
53. Hinton, R. D.; Janzen, E. G. J. Org. Chem. 1992, 57, 2646.
54. Ionita, P.; Gilbert, B. C.; Whitwood, A. C. Lett. Org. Chem. 2004, 1, 70.
55. Fujii, S.; Yoshimura, T. Coord. Chem. Rev. 2000, 198, 89.
56. Davies, M. J.; Forni, L. G.; Shuter, S. L. Chem. Biol. Interact. 1987, 61, 177.
57. Potapenko, D. I.; Bagryanskaya, E. G.; Tsentalovich, Y. P.; Reznikov, V. A.; Clanton, T. L.; Khramtsov, V. V. J. Phys. Chem. B 2004, 108, 9315.
58. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd ed.; Oxford University Press, Inc.: New York, 1999.
59. Buettner, G. R. Arch. Biochem. Biophys. 1993, 300, 535.
60. Millis, K. K.; Weaver, K. H.; Rabenstein, D. L. J. Org. Chem. 1993, 58, 4144-6.
61. Hou, Y.; Wang, J.; Arias, F.; Echegoyen, L.; Wang, P. G. Bioorg. Med. Chem. Lett. 1998, 8, 3065.
62. Zhao, Y.-L.; McCarren, P. R.; Houk, K. N.; Choi, B. Y.; Toone, E. J. J. Am. Chem. Soc. 2005, 127, 10917.
63. de Oliveira, M. G.; Shishido, S. M.; Seabra, A. B.; Morgon, N. H. J. Phys. Chem. A 2002, 106, 8963.
64. Baciu, C.; Gauld, J. W. J. Phys. Chem. A 2003, 107, 9946.
65. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
66. Bender, M. L. Chem. Rev. 1960, 60, 53.
67. Lue, J.-M.; Wittbrodt, J. M.; Wang, K.; Wen, Z.; Schlegel, H. B.; Wang, P. G.; Cheng, J.-P. J. Am. Chem. Soc. 2001, 123, 2903.
68. Arulsamy, N.; Bohle, D. S.; Butt, J. A.; Irvine, G. J.; Jordan, P. A.; Sagan, E. J. Am. Chem. Soc. 1999, 121, 7115.
69. Grossi, L.; Montevecchi, P. C. Chem.-Eur. J. 2002, 8, 380.
70. Toubin, C.; Yeung, D. Y. H.; English, A. M.; Peslherbe, G. H. J. Am. Chem. Soc. 2002, 124, 14816.
71. Shinobu, L. A.; Jones, S. G.; Jones, M. M. Acta Pharm. Toxicol. 1984, 54, 189.
72. Labanowski, J. W.; Andzelm, J. Density Functional Methods in Chemistry; Springer: New York, 1991.
73. Parr, R. G.; Yang, W. Density Functional Theory in Atoms and Molecules; Oxford University Press: New York, 1989.
74. Becke, A. D. Phys. Rev. 1988, 38, 3098.
75. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
76. Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
77. Hehre, W. J.; Radom, L.; Schleyer, P. V.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986.
78. Tornasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
79. Cossi, M.; Barone, V.; Cammi, R.; Tornasi, J. Chem. Phys. Lett. 1996, 255, 327.
80. Barone, V.; Cossi, M.; Tornasi, J. J. Chem. Phys. 1997, 107, 3210.
81. Barone, V.; Bencini, A.; Cossi, M.; Di Matteo, A.; Mattesini, M.; Totti, F. J. Am. Chem. Soc. 1998, 120, 7069.
82. Tornasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
83. Frisch, M. J.; et al. Gaussian 03, revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
84. Reed, A. E.; Curtiss, L. A.; Weinhold, F. A. Chem. Rev. 1988, 88, 899.
85. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.