Sodium nitroprusside: Mechanism of NO release mediated by sulfhydryl-containing molecules

Journal of Medicinal Chemistry

Volumn 48, Issue 7, 2005, Pages 2622-2626

  Grossi, Loris ^a   D'Angelo, Sandra ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; FERROMAGNETIC MATERIAL; GLUTATHIONE; NITRIC OXIDE; NITRIC OXIDE DONOR; NITROPRUSSIDE SODIUM; RADICAL; S NITROSOTHIOL; THIOL DERIVATIVE;

ARTICLE; DRUG EFFECT; DRUG MECHANISM; DRUG RELEASE; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

BUFFERS; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN-ION CONCENTRATION; NITRIC OXIDE; NITRIC OXIDE DONORS; NITROPRUSSIDE; PHOSPHATES; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 17144421191     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049857n     Document Type: Article

References (28)

1. (a) Scagliarini, G. Atti V Congr. Naz. Chim. Pure Appl., Rome, 1935.
2. (b) Swinehart, J. H. The nitroprusside ion. Coord. Chem. Rev. 1967, 2, 385-402.
3. (a) Butler, A. R.; Calsy-Harrison, A. M.; Glidwell, C.; Sorensen, P. E. The pentacyanonitrosylferrate ion-V. The course of the reactions of nitroprusside with a range of thiols. Polyhedron 1988, 7, 1197-1202,
4. (b) Butler, A. R.; Calsy, A. M.; Johnson, I. L. Enzyme inhibition by sodium nitroprusside. Polyhedron 1990, 9, 913-919.
5. (c) Butler, A. R.; Megson, I. L. Non-Heme Iron Nitrosyls in Biology Chem. Rev. 2002, 102, 1155-1165.
6. Leeuwenkamp, O. R. Ph.D. Thesis, University of Leiden, 1985.
7. Rochelle, L. G.; Kruszyna, H.; Kruszyna, R.; Barchowsky, A.; Wilcox, D. E.; Smith, R. P. Bioactivation of Nitroprusside by Porcine Endothelial Cells. Toxicol. Appl. Pharmacol. 1994, 128, 123-128.
8. 2- complex with biologically relevant thiols. New J. Chem. 2002, 26, 1495-1502.
9. (a) Schwane, J. D.; Ashby, M. T. FTIR Investigation of the Intermediates Formed in the Reaction of Nitroprusside and Thiolates J. Am. Chem. Soc. 2002, 124, 6822-6823.
10. (b) Carapuca, H. M.; Simao, J. E. J.; Fogg, A. G. Comproportionation and disproportionation reactions in the electrochemical reduction of nitroprusside at a hanging mercury drop electrode in acidic solution. J. Electroanal. Chem. 1988, 455, 93-105.
11. +, is reported; see: Manoharan, P. T.; Gray, H. B. Electronic Structure of Nitroprusside Ion. J. Am. Chem. Soc. 1965, 87, 3340-3348.
12. Glidewell, C.; Johnson, I. L. Definitive identification of the primary reduction product of the nitroprusside ion, pentacyanonitrosylferrate(2-), in aqueous solution Inorg. Chim. Acta 1987, 132, 145-147.
13. Cheney, R. P.; Simic, M. G.; Hoffman, M. Z.; Taub, I. A.; Asmus, K. D. One-electron reduction of pentacyanonitrosylferrate(II) ion in aqueous solution. Inorg. Chem. 1977, 16, 2187-2192.
14. Wilcox, D. E.; Kruszyna, H.; Kruszyna, R.; Smith, R. P. Effect of Cyanide on the Reaction of Nitroprusside with Hemoglobin: Relevance to Cyanide Interference with the Biological Activity of Nitroprusside. Chem. Res. Toxicol. 1990, 3, 71-76.
15. Johnson, M. D.; Wilkins, R. G. Kinetics of the Primary Interaction of Pentacyano-nitrosylferrate(2-) (Nitroprusside) with Aliphatic Thiols. Inorg. Chem. 1984, 23, 231-235.
16. Morando, P. J.; Borghi, E. B.; de Schteingart, L. M.; Blesa, M. A. The Reaction of Cysteine with Pentacyanonitrosylferrate(2-) Ion. J. C. S. Dalton 1981, 435-440.
17. 3-. Inorg. Chem. 2003, 42, 4179-4189.
18. Rindone, J. P.; Sloane, E. P. Cyanide toxicity from sodium nitroprusside: Risks and management Ann. Pharmacother. 1992, 26, 515-519.
19. Feelisch, M. The use of nitric oxide donors in pharmacological studies. Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 358, 113-122.
20. Tsikas, D.; Böger, R. H.; Bode-Böger, S. M.; Brunner, G.; Frölich, J. C. Formation od S-nitroso compounds from sodium nitroprus-side, nitric oxide or nitrite and reduced thiols: Analysis by capillary isotachophoresis. J. Chromatogr. 1995, A, 699, 363-369.
21. -10.
22. Goldstein, S.; Czapski, G. Mechanism of the Nitrosation of Thiols and Amines by Oxygenated NO Solutions: The Nature of the Nitrosating Intermediates. J. Am. Chem. Soc. 1996, 118, 3419-3425.
23. McDonald, C. C.; Phillips, W. D.; Mover, H. F. An Electron Spin Resonance Study of Some Complexes of Iron, Nitric oxide, and Anionic Ligands. J. Am. Chem. Soc. 1965, 87, 3319-3326.
24. Costanzo, S.; Menage, S.; Purrello, R.; Bonomo, R. P.; Fontecave, M. Reexamination of the formation of dinitrosyl-iron complexes during reaction of S-nitrosothiols with Fe(II). Inorg. Chim. Acta 2001, 318, 1-7.
25. Butler, A. R.; Glidewell, C.; Hyde, A. R.; Walton, J. C. Formation of paramagnetic monomolecular iron nitrosyl complexes from diamagnetic di- and tetranuclear Iron-Sulphur nitrosyls: Characterisation by EPR spectroscopy and study of thiolate and nitrosyl ligand exchange reactions. Polyhedron 1985, 5, 797-809.
26. 2 adduct should evidence an EPR spectrum with a different pattern; in fact, the D-atom is characterized by a three-line EPR pattern and an hfsc of ca. one-sixth that of the replaced H-atom. Unfortunately, when running experiments in aqueous solution, part of the deuterated cysteine goes back to the unduterated form, and then both species are involved in the reaction.
27. Grossi, L.; Montevecchi, P. C.; Strazzari, S. Decomposition of Nitrosothiols: Unimolecular versus Autocatalytic Mechanism. J. Am. Chem. Soc. 2001, 123, 4853-4854.
28. Grossi, L.; Montevecchi, P. C. A Kinetic Study of S-Nitrosothiol Decomposition. Chem. Eur. J. 2002, 8, 380-387.