On the nature of a compound formed from dinitrosyl-iron complexes with cysteine and responsible for a long-lasting vasorelaxation

Nitric Oxide - Biology and Chemistry

Volumn 22, Issue 4, 2010, Pages 266-274

  Mokh, Vladimir P ^a   Poltorakov, Alexander P ^b   Serezhenkov, Vladimir A ^b   Vanin, Anatoly F ^b  

^a INSTITUTE OF EXPERIMENTAL CARDIOLOGY   (Russian Federation)

^b SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

Dinitrosyl iron complex; Roussin's red salt thioethers; Vasorelaxation

Indexed keywords

BATHOPHENANTHROLINE DISULFONATE; CYSTEINE; DINITROSYL IRON COMPLEX; DITHIOCARBAMIC ACID DERIVATIVE; ESTER DERIVATIVE; IRON COMPLEX; N METHYL DEXTRO GLUCAMINE DITHIOCARBAMATE; N METHYLGLUCAMINE N CARBODITHIOIC ACID; NITRIC OXIDE; NITRIC OXIDE DONOR; NITRITE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ABDOMINAL AORTA; ABSORPTION; ARTICLE; DECOMPOSITION; ELECTRON SPIN RESONANCE; IRON CHELATION; MAGNETISM; MALE; NITROSYLATION; NONHUMAN; OXYGENATION; PRIORITY JOURNAL; RAT; VASCULAR RING; VASODILATATION;

ANIMALS; CYSTEINE; IRON; MALE; NITROGEN OXIDES; RATS; RATS, WISTAR; S-NITROSOTHIOLS; VASODILATION; VASODILATOR AGENTS;

RATTUS;

EID: 77949918161     PISSN: 10898603     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.niox.2010.01.002     Document Type: Article

References (32)

1. Vanin A.F., Stukan R.A., and Manukhina E.B. Physical properties of dinitrosyl iron complexes with thiol-containing ligands in relation with their vasodilator activity. Biochim. Biophys. Acta 1295 (1996) 5-12
2. Vanin A.F., Mokh V.P., Serezhenkov V.A., and Chazov E.I. Vasorelaxing activity of stable powder preparations of dinitrosyl iron complexes with cysteine or glutathione. Nitric Oxide Biol. Chem. 16 (2007) 322-330
3. McAninly J., Williams D.L.H., Askew S.C., Butler A.R., and Russell C. Metal ion catalysis in nitrosothiol (RSNO) decomposition. J. Chem. Soc. Chem. Commun. (1993) 1758-1759
4. Lundberg J.O., and Weitzberg E. NO generation from nitrite and its role in vascular control. Arterioscler. Thromb. Vasc. Biol. 25 (2005) 915-922
5. Dalsgaard T., Simonsen U., and Fago A. Nitrite-dependent vasodilation is facilitated by hypoxia and is independent of known NO-generating nitrite reductase activity. Am. J. Physiol. Heart Circ. Physiol. 292 (2007) H3072-H3078
6. Scott Isbell T., Gladwin M.T., and Patel R.P. Hemoglobin oxygen saturation regulates nitrite-dependent vasodilation of aortic ring bioassays. Am. J. Physiol. Heart Circ. Physiol. 293 (2007) H2565-H2572
7. Frerart F., Sonveaux P., Rath G., Smoos A., Meqor A., Charlier N., Jordan B.F., Saliez J., Noël A., Dessy C., Gallez B., and Feron O. The acidic tumor microenvironment promotes the reconversion of nitrite to nitric oxide: towards a new and safe radiosensitizing strategy. Cancer Ther. Preclin. 14 (2008) 2768-2774
8. Crawford J.H., Scott Isbell T., Huang Z., Shiva S., Chacko B.K., Schechter A.N., Darley-Usmar V.M., Kerby J.D., Lang J.D., Kraus D., Ho C., Gladwin M.T., and Patel R.P. Hypoxia, red blood cells, and nitrite-regulate NO-dependent hypoxic vasodilation. Blood 107 (2009) 566-574
9. Shinobu L.A., Jones S.G., and Jones M.M. Sodium N-methyl-d-glucamine dithiocarbamate and cadmium intoxication. Acta Pharmacol. Toxicol. 54 (1984) 189-194
10. Kowaluk E.A., and Fang H.-L. Spontaneous liberation of nitric oxide cannot account for in vitro vascular relaxation by S-nitrosothiols. J. Pharmacol. Exp. Ther. 255 (1990) 1256-1264
11. Butler A.R., and Rhodes P. Chemistry, analysis and biological roles of S-nitrosothiols. Anal. Biochem. 249 (1997) 1-9
12. Vanin A.F., Muller B., Alencar J.L., Lobysheva I.I., Nepveu F., and Stoclet J.-C. Evidence that intrinsic iron but not intrinsic copper determined S-nitrosocysteine decomposition in buffer solution. Nitric Oxide Biol. Chem. 7 (2002) 194-209
13. Vanin A.F., Papina A.A., Serezhenkov V.A., and Koppenol W.H. The mechanism of S-nitrosothiol decomposition catalyzed by iron. Nitric Oxide Biol. Chem. 10 (2004) 60-73
14. McDonald C.C., Philips W.D., and Mower H.F. An electron spin resonance study of some complexes of iron, nitric oxide and anionic ligands. J. Am. Chem. Soc. 87 (1965) 3319-3326
15. Burbaev D.Sh., Vanin A.F., and Blumenfeld L.A. Electronic and spatial structures of paramagnetic dinitrosyl ferrous complexes. Z. Strukt. Khimii (Rus) 2 (1971) 252-256
16. Yoshida M., Akaike T., Wada Y., Sato K., Ikeda K., Ueda S., and Maeda H. Therapeutic effects of imidazolineoxyl N-oxide against endotoxin shock through direct nitric oxide-scavenging activity. Biochim. Biophys. Res. Commun. 202 (1994) 923-930
17. 2 reaction. Chem. Res. Toxicol. 7 (1994) 519-525
18. Vanin A.F., and van Faassen E. DNICs: physico-chemical properties and their observations in cells and tissues. In: van Faassen E., and Vanin A.F. (Eds). Radicals for Life: The Various Forms of Nitric Oxide (2007), Elsevier, Amsterdam 19-74
19. Vanin A.F., Poltorakov A.P., Mikoyan V.D., Kubrina L.N., and van Faassen E. Why iron-dithiocarbamates ensure detection of nitric oxide in cells and tissues. Nitric Oxide Biol. Chem. 15 (2006) 295-311
20. Butler A.R., and Megson I.L. Non-heme iron nitrosyls in biology. Chem. Rev. 102 (2002) 1155-1165
21. Conrado C.L., Bourassa J.L., Egler C., Weksler S., and Ford P.C. Photochemical investigation of Roussin's red salt ether: Fe(μ-SR)(NO). Inorg. Chem. 42 (2003) 2288-2293
22. 9 electronic coupling: new members of a class of dinitrosyl iron complexes. Inorg. Chem. 44 (2005) 3226-3232
23. 10 DNICs. Inorg. Chem. 46 (2007) 5110-5117
24. -: relevance to the products of nitrosylation of cytosolic and mitochondrial aconitases, and high-potential iron proteins. J. Am. Chem. Soc. 129 (2007) 12626-12627
25. 2} DNIC. J. Am. Chem. Soc. 130 (2008) 10929-10938
26. Chiang C.-Y., and Darensbourg M.Y. Iron nitrosyl complexes as models for biological nitric oxide transfer reagents. J. Biol. Inorg. Chem. 11 (2008) 359-370
27. 4] (R = n-Pr, t-Bu, 6-methyl-2-pyridil and 4,6-dimethyl-2-pyrimidil): synthesis, X-ray crystal structures, spectroscopic, electrochemical and density functional theoretical investigations. Dalton Trans. (2009) 777-786
28. Butler A.R., Glidewell C., Hyde A.R., and Walton J.C. Formation of paramagnetic mononuclear iron nitrosyl complexes from diamagnetic di- and tetranuclear iron-sulphur nitrosyls: characterization by EPR spectroscopy and study of thiolate and nitrosyl ligand exchange reactions. Polyhedron 4 (1988) 797-809
29. Vedernikov Yu.P., Mordvintcev P.I., Malenkova I.V., and Vanin A.F. Similarity between the vasorelaxing activity of dinitrosyl iron cysteine complexes and endothelium-derived relaxing factor. Eur. J. Pharmacol. 211 (1992) 313-317
30. Vanin A.F. Dinitrosyl iron complexes with thiolate ligands: physico-chemistry, biochemistry and physiology. Nitric Oxide Biol. Chem. 21 (2009) 1-13
31. 3SONO studied by density functional theory method. Bull. Korean Chem. Soc. 25 (2004) 1657-1660
32. Balazy M., Kaminski P.M., Mao K., Tan J., and Wolin M.S. S-Nitroglutathione, a product of the reaction between peroxynitrite and glutathione that generates nitric oxide. J. Biol. Chem. 273 (1998) 32009-32015