15N NMR and electronic properties of S-nitrosothiols

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 19, 1999, Pages 2897-2902

  Wang, Kun ^a   Hou, Yongchun ^a   Zhang, Wei ^a   Ksebati, Mohamad B ^a   Xian, Ming ^a   Cheng, Jin Pei ^b   Wang, Peng George ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTATHIONE; N ACETYL S NITROSOPENICILLAMINE; NITRIC OXIDE; S NITROSOCAPTOPRIL; THIOL DERIVATIVE; DRUG DERIVATIVE; NITROSO DERIVATIVE; PAPAIN; PENICILLAMINE; S NITRO N ACETYLPENICILLAMINE; S-NITRO-N-ACETYLPENICILLAMINE;

ARTICLE; CHEMICAL ANALYSIS; DRUG STRUCTURE; EQUILIBRIUM CONSTANT; LIGHT ABSORPTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STRUCTURE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION; ULTRAVIOLET SPECTROPHOTOMETRY;

GLUTATHIONE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITRIC OXIDE; NITROSO COMPOUNDS; OXIDATION-REDUCTION; PAPAIN; PENICILLAMINE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0033523509     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00499-0     Document Type: Article

References (25)

1. 1. (a) Moncada, S.; Palmer, R. M. J.; Higgs, E. A. Pharmacol. Rev. 1991, 43, 109. (b) Beckman, J. S. In The Physiological and Pathological Chemistry of Nitric Oxide: Nitric Oxide, Principles and Actions; Lancaster, J. Jr., Ed.; Academic: San Diego; 1996; pp 1 - 69. (c) Fukuto, J. M. In Chemistry of Nitric Oxide: Biologically Relevant Aspects, Nitric Oxide, Biochemistry, Molecular Biology, and Therapeutic Implications; Ignarro, L., Murad, F.; Eds.; Academic: San Diego; 1995; p 1.
2. 1. (a) Moncada, S.; Palmer, R. M. J.; Higgs, E. A. Pharmacol. Rev. 1991, 43, 109. (b) Beckman, J. S. In The Physiological and Pathological Chemistry of Nitric Oxide: Nitric Oxide, Principles and Actions; Lancaster, J. Jr., Ed.; Academic: San Diego; 1996; pp 1 - 69. (c) Fukuto, J. M. In Chemistry of Nitric Oxide: Biologically Relevant Aspects, Nitric Oxide, Biochemistry, Molecular Biology, and Therapeutic Implications; Ignarro, L., Murad, F.; Eds.; Academic: San Diego; 1995; p 1.
3. 1. (a) Moncada, S.; Palmer, R. M. J.; Higgs, E. A. Pharmacol. Rev. 1991, 43, 109. (b) Beckman, J. S. In The Physiological and Pathological Chemistry of Nitric Oxide: Nitric Oxide, Principles and Actions; Lancaster, J. Jr., Ed.; Academic: San Diego; 1996; pp 1 - 69. (c) Fukuto, J. M. In Chemistry of Nitric Oxide: Biologically Relevant Aspects, Nitric Oxide, Biochemistry, Molecular Biology, and Therapeutic Implications; Ignarro, L., Murad, F.; Eds.; Academic: San Diego; 1995; p 1.
4. 2. Williams, D. L. H. Chem. Soc. Rev. 1985, 171.
5. 3. Stamler, J. S. In S-Nitrosothiols and the Bioregulatory Actions of Nitric Oxides through Reactions with Thiol Groups: The Role of Nitric Oxide in Physiology and Pathophysiology; Koprowski, H.; Maeda, H., Eds.; Springer-Verlag: New York; 1993; p 19.
6. 4. Radomski, M. W.; Rees, D. D.; Dutra, A.; Moncada, S. Br. J. Pharmacol. 1992, 107, 745.
7. 5. (a) Jia, L.; Blantz, R. C. Eur. J. Pharmacol. 1998, 354, 33. (b) Nakae, I. J. Pharmaco;. Exp. Ther. 1995, 274, 40.
8. 5. (a) Jia, L.; Blantz, R. C. Eur. J. Pharmacol. 1998, 354, 33. (b) Nakae, I. J. Pharmaco;. Exp. Ther. 1995, 274, 40.
9. 6. (a) Stamler, J. S.; Jia, L.; Eu, J. P.; McMahon, T. J.; Demchenko, I. T.; Bonaventura, J.; Gernet, K.; Piantadosi, C. A. Science 1997, 276, 2034. (b) Mannick, J. B.; Hausladen A.; Liu L.; Hess, D. T.; Zeng, M.; Miao, Q. X.; Kane, L. S.; Gow, A. J.; Stamler, J. S. Science 1999, 284, 651.
10. 6. (a) Stamler, J. S.; Jia, L.; Eu, J. P.; McMahon, T. J.; Demchenko, I. T.; Bonaventura, J.; Gernet, K.; Piantadosi, C. A. Science 1997, 276, 2034. (b) Mannick, J. B.; Hausladen A.; Liu L.; Hess, D. T.; Zeng, M.; Miao, Q. X.; Kane, L. S.; Gow, A. J.; Stamler, J. S. Science 1999, 284, 651.
11. 7. Xu, L.; Eu. J. P. Meissner, G.; Stamler, J. S. Science 1998, 279, 235.
12. 8. (a) Le, M.; Zhang, H.; Means, G. E. Bioorg. Med. Chem. Lett. 1997, 7, 1393. (b) Hou, Y. C.; Wang, J. Q.; Arias, F.; Echegoyen, L.; Wang, P. G. Bioorg. Med. Chem. Lett. 1998, 8, 3065.
13. 8. (a) Le, M.; Zhang, H.; Means, G. E. Bioorg. Med. Chem. Lett. 1997, 7, 1393. (b) Hou, Y. C.; Wang, J. Q.; Arias, F.; Echegoyen, L.; Wang, P. G. Bioorg. Med. Chem. Lett. 1998, 8, 3065.
14. 9. Levy, G. C.; Lichter, R. L. Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy; John Wiley & Sons: New York; 1979; pp 167 - 213.
15. 10. Bonnett, R.; Holleyhead, R.; Johnson, B. L.; Randall, E. W. J. Chem. Soc., Perkin Trans. 1 1975, 2261.
16. 11. Stamler, J. S.; Simon, D. I.; Osborne, J. A.; Mullins, M. E.; Jaraki, O.; Michel, T.; Singel, D. J.; Loscalzo, J. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 444.
17. 12. Simon, D. I.; Mullins, M. E.; Jia, L.; Gaston, B.; Singel, D. J.; Stamler, J. S. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 4736.
18. 13. Guo, Z. M.; Ramirez, J.; Li, J.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 3726.
19. 14. Williams, D. L. H. Chem. Commun. 1996, 10, 1085
20. 15. Levy, G. C.; Lichter, R. L. Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy; John Wiley & Sons: New York; 1979; pp 83 - 91.
21. 16. Meyer, D. J.; Kramer, H.; Ozer, N.; Coles, B.; Ketterer, B. FEBS Lett. 1994, 345, 177
22. 17. Jencks, W. P.; Regenstein, J. In The Handbook of Biochemistry-Selected Data for Molecular Biology; Sober, H. A. Ed.; The Chemical Rubber Co.; Cleveland, 1968, p186.
23. 18. Ramirez, J.; Yu, L. B.; Li, J.; Braunschweiger, P. G.; Wang, P. G. Bioorg. Med. Chem. Lett. 1996, 6, 2575.
24. 19. Field, L.; Dilts, R. V.; Ravichandran, R.; Lenhert, P, G.; Carnahan, G. J. Chem. Soc. Chem. Commun. 1978, 249.
25. 20. Hart, T. W. Tetrahedron Lett. 1985, 2013.