Membrane penetration of nitric oxide and its donor S-nitroso-N- acetylpenicillamine: A spin-label electron paramagnetic resonance spectroscopic study

Biochimica et Biophysica Acta - Biomembranes

Volumn 1661, Issue 2, 2004, Pages 135-143

  Nedeianu, Saviana ^a   Páli, Tibor ^a,b   Marsh, D ^b  

^a INSTITUTE OF BIOCHEMISTRY   (Hungary)

^b MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

Author keywords

1,2 dimyristoyl sn glycero 3 phosphocholine; Continuous wave; CW; DMPC; Electron paramagnetic resonance; EPR; Membrane penetration; N PCSL; Nitric oxide; NO; NO donor; Spin label; Spin relaxation enhancement

Indexed keywords

DIMYRISTOYLPHOSPHATIDYLCHOLINE; N ACETYL S NITROSOPENICILLAMINE; NITRIC OXIDE; OXYGEN;

ARTICLE; BILAYER MEMBRANE; CELL MEMBRANE PERMEABILITY; CONCENTRATION (PARAMETERS); ELECTRON SPIN RESONANCE; HYDROPHOBICITY; LIPID BILAYER; LIPID MEMBRANE; PRIORITY JOURNAL; SPIN LABELING; THERMOSTABILITY;

CELL MEMBRANE; ELECTRON SPIN RESONANCE SPECTROSCOPY; LIPID BILAYERS; MEMBRANE LIPIDS; NITRIC OXIDE; NITRIC OXIDE DONORS; OXYGEN; PERMEABILITY; PHOSPHOLIPIDS; S-NITROSO-N-ACETYLPENICILLAMINE; SPIN LABELS;

EID: 1542270807     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2003.12.008     Document Type: Article

References (58)

1. Koshland D.E. The molecule of the year. Science. 258:1992;1861.
2. Delledonne M., Xia Y.J., Dixon R.A., Lamb C. Nitric oxide functions as a signal in plant disease resistance. Nature. 394:1998;585-588.
3. Ignarro L.J. Nitric oxide: a unique endogenous signaling molecule in vascular biology (Nobel lecture). Angew. Chem., Int. Ed. 38:1999;1882-1892.
4. Murad F. Discovery of some of the biological effects of nitric oxide and its role in cell signaling. Biosci. Rep. 19:1999;133-154.
5. Murad F. The excitement and rewards of research with our discovery of some of the biological effects of nitric oxide. Circ. Res. 92:2003;339-341.
6. Bian K., Murad F. Nitric oxide (NO) - biogeneration, regulation, and relevance to human diseases. Front. Biosci. 8:2003;D264-D278.
7. Wink D.A., Mitchell J.B. Chemical biology of nitric oxide: insights into regulatory, cytotoxic, and cytoprotective mechanisms of nitric oxide. Free Radic. Biol. Med. 25:1998;434-456.
8. Davis K.L., Martin E., Turko I.V., Murad F. Novel effects of nitric oxide. Annu. Rev. Pharmacol. Toxicol. 41:2001;203-236.
9. Barouch L.A., Harrison R.W., Skaf M.W., Rosas G.O., Cappola T.P., Kobeissi Z.A., Hobai I.A., Lemmon C.A., Burnett A.L., O'Rourke B., Rodriguez E.R., Huang P.L., Lima J.A.C., Berkowitz D.E., Hare J.M. Nitric oxide regulates the heart by spatial confinement of nitric oxide synthase isoforms. Nature. 416:2002;337-340.
10. Nisoli E., Clementi E., Paolucci C., Cozzi V., Tonello C., Sciorati C., Bracale R., Valerio A., Francolini M., Moncada S., Carruba M.O. Mitochondrial biogenesis in mammals: the role of endogenous nitric oxide. Science. 2003;899.
11. 2 and peroxinitrite in membranes: physiological implications. Free Radic. Res. 31:1990;597-606.
12. Griffith O.W., Stuehr D.J. Nitric oxide synthases: properties and catalytic mechanism. Annu. Rev. Physiol. 57:1995;707-736.
13. Cleeter M.W.J., Cooper J.M., Darley-Usmar V.M., Moncada S., Schapira A.H.V. Reversible inhibition of cytochrome c oxidase, the terminal enzyme of the mitochondrial respiratory chain, by nitric oxide - implications for neurodegenerative diseases. FEBS Lett. 345:1994;50-54.
14. Pawloski J.R., Hess D.T., Stamler J.S. Export by red blood cells of nitric oxide bioactivity. Nature. 409:2001;622-626.
15. Rubbo H., Radi R., Trujillo M., Telleri R., Kalyanaraman B., Barnes S., Kirk M., Freeman B.A. Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation - formation of novel nitrogen-containing oxidized lipid derivatives. J. Biol. Chem. 269:1994;26066-26075.
16. Rubbo H., Radi R., Anselmi D., Kirk M., Barnes S., Butler J., Eiserich J.P., Freeman B.A. Nitric oxide reaction with lipid peroxyl radicals spares α-tocopherol during lipid peroxidation - greater oxidant protection from the pair nitric oxide/α-tocopherol than α-tocopherol/ascorbate. J. Biol. Chem. 275:2000;10812-10818.
17. Abraham M.H., Gola J.M.R., Cometto-Muniz J.E., Cain W.S. The solvation properties of nitric oxide. J. Chem. Soc., Perkin Trans. 2:2000;2067-2070.
18. Marchettini N., Rustici M., Branca M., Culeddu N., Fruianu M., Serra M.V., Tiezzi E. Solubility of nitric oxide (NO) in lipid aggregates as monitored by nuclear magnetic resonance. Colloids Surf. 131:1998;1-6.
19. Denicola A., Souza J.M., Radi R., Lissi E. Nitric oxide diffusion in membranes determined by fluorescence quenching. Arch. Biochem. Biophys. 328:1996;208-212.
20. Subczynski W.K., Lomnicka M., Hyde J.S. Permeability of nitric oxide through lipid bilayer membranes. Free Radic. Res. Commun. 24:1996;343-349.
21. Bainbrigge N., Butler A.R., Gorbitz C.H. The thermal stability of S-nitrosothiols: experimental studies and ab initio calculations on model compounds. J. Chem. Soc., Perkin Trans. 2:1997;351-353.
22. Goto K., Hino Y., Kawashima T., Kaminaga M., Yano E., Yamamoto G., Takagi N., Nagase S. Synthesis and crystal structure of a stable S-nitrosothiol bearing a novel steric protection group and of the corresponding S-nitrothiol. Tetrahedron Lett. 41:2000;8479-8483.
23. Megson I.L., Greig I.R., Butler A.R., Gray G.A., Webb D.J. Therapeutic potential of S-nitrosothiols as nitric oxide donor drugs. Scott. Med. J. 42:1997;88-89.
24. Napoli C., Ignarro L.J. Nitric oxide-releasing drugs. Annu. Rev. Pharmacol. Toxicol. 43:2003;97-123.
25. Wang P.G., Xie H., Tang X.P., Wu X.J., Wen Z., Cai T.W., Janczuk A.J. Nitric oxide donors: chemical activities and biological applications. Chem. Rev. 102:2002;1091-1134.
26. Singh R.J., Hogg N., Joseph J., Kalyanaraman B. Mechanism of nitric oxide release from S-nitrosothiols. J. Biol. Chem. 271:1996;18596-18603.
27. Hou Y.C., Wang J.Q., Arias F., Echegoyen L., Wang P.G. Electrochemical studies of S-nitrosothiols. Bioorg. Med. Chem. Lett. 8:1998;3065-3070.
28. Megson I.L., Greig I.R., Gray G.A., Webb D.J., Butler A.R. Prolonged effect of a novel S-nitrosated glyco amino acid in endothelium-denuded rat femoral arteries: potential as a slow release nitric oxide donor drug. Br. J. Pharmacol. 122:1997;1617-1624.
29. Gutierrez H.H., Nieves B., Chumley P., Rivera A., Freeman B.A. Nitric oxide regulation of superoxide-dependent lung injury: oxidant-protective actions of endogenously produced and exogenously administered nitric oxide. Free Radic. Biol. Med. 21:1996;43-52.
30. Hogg N., Kalyanaraman B., Joseph J., Struck A., Parthasarathy S. Inhibition of low density lipoprotein oxidation by nitric oxide - potential role in atherogenesis. FEBS Lett. 334:1993;170-174.
31. Ramirez J., Yu L.B., Li J., Braunschweiger P.G., Wang P.G. Glyco-S-nitrosothiols, a novel class of NO donor compounds. Bioorg. Med. Chem. Lett. 6:1996;2575-2580.
32. Carnahan G.E., Lenhert P.G., Ravichandran R. S-nitroso-n-acetyl-DL- penicillamine. Acta Crystallogr., B. 34:1978;2645-2648.
33. Field L.R., Dilts R.V., Ravichandran R., Lenhert P.G., Carnahan G.E. Unusually stable thionitrite from n-acetyl-D,L-penicillamine - X-ray crystal and molecular structure of 2-(acetylamino)-2-carboxy-1,1-dimethylethyl thionitrite. J. Chem. Soc., Chem. Commun. 6:1978;249-250.
34. Dzikovski B.G., Livshits V.A., Marsh D. Oxygen permeation profile in lipid membranes: non-linear spin-label EPR. Biophys. J. 85:2003;1005-1012.
35. Marsh D., Watts A. Spin-labeling and lipid-protein interactions in membranes. Jost P.C., Griffith O.H. Lipid-Protein Interactions. vol. 2:1982;53-126 Wiley-Interscience, New York.
36. Fajer P., Marsh D. Microwave and modulation field inhomogeneities and the effect of cavity Q in saturation transfer ESR spectra. Dependence on sample size. J. Magn. Reson. 49:1982;212-224.
37. Fajer P., Watts A., Marsh D. Saturation transfer, continuous wave saturation, and saturation recovery electron spin resonance studies of chain-spin labeled phosphatidylcholines in the low temperature phases of dipalmitoyl phosphatidylcholine bilayers. Effects of rotational dynamics and spin-spin interactions. Biophys. J. 61:1992;879-891.
38. Páli T., Horváth L.I., Marsh D. Continuous-wave saturation of two-component, inhomogeneously broadened, anisotropic EPR spectra. J. Magn. Reson., A. 101:1993;215-219.
39. Livshits V.A., Páli T., Marsh D. Relaxation time determinations by progressive saturation EPR: effects of molecular motion and Zeeman modulation for spin labels. J. Magn. Reson. 133:1998;79-91.
40. Singh R.J., Hogg N., Mchaourab H.S., Kalyanaraman B. Physical and chemical interactions between nitric oxide and nitroxides. Biochim. Biophys. Acta. 1201:1994;437-441.
41. McConnell H.M. Molecular motion in biological membranes. Berliner L.J. Spin Labeling. Theory and Applications. vol. 1:1976;525-560 Academic Press, New York.
42. Moser M., Marsh D., Meier P., Wassmer K.-H., Kothe G. Chain configuration and flexibility gradient in phospholipid membranes. Comparison between spin-label electron spin resonance and deuteron nuclear magnetic resonance, and identification of new conformations. Biophys. J. 55:1989;111-123.
43. Páli T., Livshits V.A., Marsh D. Dependence of saturation-transfer EPR intensities on spin-lattice relaxation. J. Magn. Reson., B. 113:1996;151-159.
44. Lancaster J.R. Simulation of the diffusion and reaction of endogenously produced nitric oxide. Proc. Natl. Acad. Sci. U. S. A. 91:1994;8137-8141.
45. Subczynski W.K., Hyde J.S., Kusumi A. Oxygen permeability of phosphatidylcholine-cholesterol membranes. Proc. Natl. Acad. Sci. U. S. A. 86:1989;4474-4478.
46. 1 method. Biochim. Biophys. Acta. 643:1981;283-291.
47. Livshits V.A., Dzikovski B.G., Marsh D. Mechanism of relaxation enhancement of spin labels in membranes by paramagnetic ion salts: dependence on 3d and 4f ions and on the anions. J. Magn. Reson. 148:2001;221-237.
48. Altenbach C., Greenhalgh D.A., Khorana H.G., Hubbell W.L. A collision gradient method to determine the immersion depth of nitroxides in lipid bilayers: application to spin-labeled mutants of bacteriorhodopsin. Proc. Natl. Acad. Sci. U. S. A. 91:1994;1667-1671.
49. Marsh D. Polarity and permeation profiles in lipid membranes. Proc. Natl. Acad. Sci. U. S. A. 98:2001;7777-7782.
50. Lide D.R. Handbook of Chemistry and Physics. 1990;CRC Press, Boca Raton, FL.
51. Strzalka K., Sarna T., Hyde J.S. ESR oxymetry: measurement of photosynthetic oxygen evolution by spin-probe technique. Photobiochem. Photobiophys. 12:1986;67-71.
52. Subczynski W.K., Hyde J.S., Kusumi A. Effect of alkyl chain unsaturation and cholesterol intercalation on oxygen transport in membranes - a pulse ESR spin labeling study. Biochemistry. 30:1991;8578-8590.
53. Ligeza A., Tikhonov A., Hyde J., Subczynski W. Oxygen permeability of thylakoid membranes - electron paramagnetic resonance spin labeling study. Biochim. Biophys. Acta. 1365:1998;453-463.
54. Marsh D. Handbook of Lipid Bilayers. 1990;CRC Press, Boca Raton, FL.
55. 2 within the hydrophobic interior of biological membranes. Proc. Natl. Acad. Sci. U. S. A. 95:1998;2175-2179.
56. Altenbach C., Marti T., Khorana H.G., Hubbell W.L. Transmembrane protein structure: spin labelling of bacteriorhodopsin mutants. Science. 248:1990;1088-1092.
57. Hubbell W.L., Altenbach C. Investigation of structure and dynamics in membrane proteins using site-directed spin labeling. Curr. Opin. Struct. Biol. 4:1994;566-573.
58. Marsh D., Páli T., Horváth L.I. Progressive saturation and saturation transfer EPR for measuring exchange processes and proximity relations in membranes. Berliner L.J. Spin Labeling. The Next Millenium. vol. 14:1998;23-82 Plenum, New York.