Redox properties of iron-dithiocarbamates and their nitrosyl derivatives: Implications for their use as traps of nitric oxide in biological systems

Biochimica et Biophysica Acta - General Subjects

Volumn 1474, Issue 3, 2000, Pages 365-377

  Vanin, Anatoly F ^a,b   Liu, Xiaoping ^a   Samouilov, Alexandre ^a   Stukan, Reonald A ^b   Zweier, Jay L ^a  

^a Laboratory of Cellular and Molecular Biology   (United States)

^b SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

Electron paramagnetic resonance; Iron dithiocarbamate complex; Nitric oxide; Spin trapping

Indexed keywords

ASCORBIC ACID; CYSTEINE; DEFEROXAMINE MESYLATE; DIETHYLDITHIOCARBAMIC ACID; DIMETHYL SULFOXIDE; DITHIOCARBAMIC ACID DERIVATIVE; HYDROQUINONE; IRON COMPLEX; N METHYLGLUCAMINE N CARBODITHIOIC ACID; NITRIC OXIDE;

ARTICLE; CHEMOLUMINESCENCE; COMPLEX FORMATION; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; SPIN TRAPPING;

DIMETHYL SULFOXIDE; ELECTRON SPIN RESONANCE SPECTROSCOPY; FERROUS COMPOUNDS; MODELS, CHEMICAL; NITRIC OXIDE; OXIDATION-REDUCTION; SPECTROPHOTOMETRY; SPECTROSCOPY, MOSSBAUER; THIOCARBAMATES;

EID: 0034193678     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-4165(00)00033-7     Document Type: Article

References (32)

1. Vanin A.F., Mordvintcev P.I., Kleschyov A.L. Appearance of nitric oxide in animal tissues in vivo. Studia Biophys. 102:1984;135-143.
2. Kubrina L.N., Caldwell W.S., Mordvincev P.I., Malenkova I.V., Vanin A.F. EPR evidence for nitric oxide production from guanidino nitrogen of L-arginine in animal tissues in vivo. Biochim. Biophys. Acta. 1099:1992;233-237.
3. Tominaga T., Sato S., Ohnishi T., Ohnishi S.T. Potentiation of nitric oxide formation following with bilateral carotid occlusion and local cerebral ischemia in the rat: in vivo detection of the nitric oxide radical by electron paramagnetic resonance spin trapping. Brain Res. 614:1993;342-346.
4. Mülsch A., Busse R., Mordvintcev P.I., Vanin A.F., Nielsen E.O., Scheel-Kruger J., Olesen S.-P. Nitric oxide promotes seizure activity in kainate-treated rats. NeuroReports. 5:1994;2325-2328.
5. Laskin D.L., DelValle M.R., Heck D.E., Hwang S.M., Durham S.K., Ohnishi S.T., Goller N.L., Laskin J.D. Hepatic nitric oxide production following acute endotoxemia in rats is mediated by increase inducible nitric oxide synthase expressiion. Hepatology. 22:1995;223-234.
6. Bune A.J., Shergil J.K., Cammack R., Cook H.T. L-arginine depletion by arginase induced nitric oxide production in endotoxic shock: an electron paramagnetic resonance study. FEBS Lett. 366:1995;127-130.
7. Vanin A.F. Iron diethyldithiocarbamate as a spin trap for nitric oxide detection. Methods Enzymol. 301:1999;269-279.
8. Lai C.-S., Komarov A.M. Spin trapping of nitric oxide produced in vivo in septic-shock mice. FEBS Lett. 345:1994;120-124.
9. Komarov A.M., Lai C.-S. Detection of nitric oxide production in mice by spin-trapping electron paramagnetic resonance spectroscopy. Biochim. Biophys. Acta. 1272:1995;29-36.
10. Zweier J.L., Wang P., Samouilov A., Kuppusamy P. Enzyme-independent formation of nitric oxide in biological tissues. Nature Med. 1:1995;804-809.
11. Zweier J.L., Wang P., Kuppusamy P. Direct measurment of nitric oxide generation in the ischemic heart using electron paramagnetic resonance spectroscopy. J. Biol. Chem. 270:1995;304-307.
12. Kuppusamy P., Wang P., Samouilov A., Zweier J.L. Spatial mapping of nitric oxide generation in the ischemic heart using electron paramagnetic resonance imaging. Magn. Res. Med. 36:1996;212-218.
13. Yoshimura T., Yokoyama H., Fujii S., Takayama F., Oikawa K., Kamada H. In vivo EPR detection and imaging of endogenous NO in LPS-treated mice. Nature Biotechnol. 14:1996;992-994.
14. Fujii H., Koscielniak J., Berliner L.J. Determination and characterization of nitric oxide generation in mice in vivo L-band EPR spectroscopy. Magn. Res. Med. 38:1997;565-568.
15. 2+ with diethyldithiocarbamate or N-methyl-D-glucamine dithiocarbamate as traps of nitric oxide in animal tissues: comparative investigations. Biochim. Biophys. Acta. 1336:1997;225-234.
16. Kotake Y., Moore D.R., Sang H., Reinke L.A. Continuous monitoring of in vivo nitric oxide formation using EPR analysis in biliary flow. Nitric Oxide: Biol. Chem. 3:1999;114-122.
17. Goodman B.A., Raynor J.B., Symons M.C.R. Electron spin resonance of (N′,N-diethyldithiocarbamato)nitrosyl iron. J. Chem. Soc. (A):1969;2572-2575.
18. 2. Inorg. Chem. 16:1977;1876-1883.
19. Mülsch A., Vanin A., Mordvintcev P., Hauschildt S., Buss R. NO accounts completely for the oxygenated nitrogen species generated by enzymic L-arginine oxygenation. Biochem. J. 288:1992;597-603.
20. Tsuchiya K., Takasugi M., Minakchi K., Fukuzawa K. Sensitive quantitation of nitric oxide by EPR spectroscopy. Free Radic. Biol. Med. 21:1996;733-737.
21. Hoshino M., Maeda M., Konishi R., Seki H., Ford P.C. Studies on the reaction mechanism for reductive nitrosylation of ferrihemoproteins in buffer solutions. J. Am. Chem. Soc. 118:1995;5702-5707.
22. B.B. Wayland, L.W. Olson, Nitric oxide complexes of iron(II) and iron(III) porphyrins, J. Chem. Soc. Chem. Commun. (1973) 897-898.
23. Shinobu L.A., Jones S.G., Jones M.M. Sodium N-methyl-D-glucamine dithiocarbamate and cadmium intoxication. Acta Pharmacol. Toxicol. 54:1984;189-194.
24. Kuppusamy P., Zweier J.L. Identification and quantification of free radicals and paramagnetic centers from complex multicomponent EPR spectra. Appl. Radiat. Isot. 44:1992;367-372.
25. Samouilov A., Kuppusamy J.L., Zweier J.L. Evaluation of the magnitude and rate of nitric oxide production from nitrite in biological systems. Arch. Biochem. Biophys. 357:1998;1-7.
26. Vanin A.F. Roles of iron ions and cysteine in formation and decomposition of S-nitrosocysteine and S-nitrosoglutathione. Biochemistry (Moscow). 60:1995;441-447.
27. Danon J. Electronic structure of transition metal complexes with nitrosyl ligands: Mossbauer effect investigation. J. Chem. Phys. 41:1964;3378-3390.
28. Kita Y., Hirasawa Y., Maeda K., Nishio M., Yoshida K. Spontaneous nitric oxide release accounts for the potent pharmacological actions of FK409. Eur. J. Pharmacol. 257:1994;123-130.
29. Paschenko S.V., Khramtsov V.V., Scatchkov M.P., Plyusnin V.F., Bassenge E. EPR and laser flash photolis studies of the reaction of nitric oxide with water soluble NO trap Fe(II)-proline-dithiocarbamate complex. Biochem. Biophys. Res. Commun. 225:1996;577-584.
30. S. Fujii, T. Yoshimura, H. Kamada, Nitric oxide trapping efficiencies of water-soluble iron(III) complexes with dithiocarbamate derivatives, Chem. Lett. (1996) 785-786.
31. Tsuchiya K., Jiang J.-J., Yoshizumi M., Tamaki T., Houchi H., Minakuchi K., Fukuzawa K., Mason R.P. Nitric oxide-forming reactions of the water-soluble nitric oxide spin-trapping agent, MGD. Free Radic. Biol. Med. 27:1999;347-355.
32. Kubrina L.N., Mikoyan V.D., Mordvintcev P.I., Vanin A.F. Iron potentiates lipopolysaccharide-induced nitric oxide formation in animal organs. Biochim. Biophys. Acta. 1176:1993;240-244.