Organic Nitrites and NO: Inhibition of Lipid Peroxidation and Radical Reactions

Chemical Research in Toxicology

Volumn 17, Issue 2, 2004, Pages 185-196

  Nicolescu, Adrian C ^a   Reynolds, James N ^a   Barclay, L Ross C ^b   Thatcher, Gregory R J ^c  

^a QUEEN S UNIVERSITY   (Canada)

^b MOUNT ALLISON UNIVERSITY   (Canada)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 DECYL NITRITE; 1 DODECYL NITRITE; 2 PHENOXY 1 ETHYL NITRITE; AMYL NITRITE; NITRIC OXIDE; NITRITE; ORGANIC NITRITE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMOLUMINESCENCE; DENSITY FUNCTIONAL THEORY; IC 50; LIPID PEROXIDATION; MEASUREMENT; STOICHIOMETRY; SYNAPTOSOME;

ANIMALS; LIPID PEROXIDATION; NITRIC OXIDE; NITRITES; RATS; RATS, SPRAGUE-DAWLEY; THERMODYNAMICS;

EID: 1342289357     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx034097p     Document Type: Article

References (83)

1. Brunton, T. L. (1867) On the use of nitrite of amyl in angina pectoris. Lancet 2, 97.
2. Furchgott, R. E. (1999) Endothelium-derived relaxing factor: discovery, early studies, and identifcation as nitric oxide (Nobel Lecture). Angew. Chem. Int. Ed. 38, 1870-1880.
3. Ignarro, L. J. (1999) Nitric Oxide: A unique endogenous signaling molecule in vascular biology (Nobel Lecture). Angew. Chem. Int. Ed. 38, 1882-1892.
4. Murad, F. (1999) Discovery of some of the biological effects of nitric oxide and Its role in cell signaling (Nobel Lecture). Angew. Chem. Int. Ed. 38, 1856-1868.
5. Moncada, S., Palmer, R. M., and Higgs, E. A. (1991) Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 43, 109-142.
6. Thatcher, G. R. J., and Weldon, H. (1998) NO problem for nitroglycerin: organic nitrate chemistry and therapy. Chem. Soc. Rev. 27, 331-337.
7. Moya, M. P., Gow, A. J., Califf, R. M., Goldberg, R. N., and Stamler, J. S. (2002) Inhaled ethyl nitrite gas for persistent pulmonary hypertension of the newborn. Lancet 360, 141-143.
8. Burgaud, J. L., Ongini, E., and Del Soldato, P. (2002) Nitric oxide-releasing drugs: a novel class of effective and safe therapeutic agents. Ann. N. Y. Acad. Sci. 962, 360-371.
9. Smith, S., Dringenberg, H. C., Bennett, B. M., Thatcher, G. R., and Reynolds, J. N. (2000) A novel nitrate ester reverses the cognitive impairment caused by scopolamine in the Morris water maze. Neuroreport 11, 3883-3886.
10. Reynolds, J. N., Bennett, B. M., Boegman, R. J., Jhamandas, K., Ratz, J. D., Zavorin, S. I., Scutaru, D., Dumitrascu, A., and Thatcher, G. R. J. (2002) Neuroprotection against Ischemic brain injury conferred by a novel nitrate ester. Bioorg. Med. Chem. Lett. 12, 2863-2866.
11. Marletta, M. A. (1994) Nitric oxide synthase: aspects concerning structure and catalysis. Cell 78, 927-930.
12. Raman, C. S., Li, H., Martasek, P., Kral, V., Masters, B. S., and Poulos, T. L. (1998) Crystal structure of constitutive endothelial nitric oxide synthase: a paradigm for pterin function involving a novel metal center. Cell 95, 939-950.
13. Graziewicz, M., Wink, D. A., and Laval, F. (1996) Nitric oxide inhibits DNA ligase activity: potential mechanisms for NO-mediated DNA damage. Carcinogenesis 17, 2501-2505.
14. Wink, D. A., and Mitchell, J. B. (1998) Chemical biology of nitric oxide: Insights into regulatory, cytotoxic, and cytoprotective mechanisms of nitric oxide. Free Radical Biol. Med. 25, 434-456.
15. Beckman, J. S., and Koppenol, W. H. (1996) Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and ugly. Am. J. Physiol. 271, C1424-C1437.
16. Halliwell, B., Hu, M. L., Louie, S., Duvall, T. R., Tarkington, B. K., Motchnik, P., and Cross, C. E. (1992) Interaction of nitrogen dioxide with human plasma. Antioxidant depletion and oxidative damage. FEBS Lett. 313, 62-66.
17. Crow, J. P., and Ischiropoulos, H. (1996) Detection and quantitation of nitrotyrosine residues in proteins: in vivo marker of peroxynitrite. Methods Enzymol. 269, 185-194.
18. Ischiropoulos, H. (1998) Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch. Biochem. Biophys. 356, 1-11.
19. Reiter, C. D., Teng, R. J., and Beckman, J. S. (2000) Superoxide reacts with nitric oxide to nitrate tyrosine at physiological pH via peroxynitrite. J. Biol. Chem. 275, 32460-32466.
20. Byun, J., Mueller, D. M., Fabjan, J. S., and Heinecke, J. W. (1999) Nitrogen dioxide radical generated by the myeloperoxidase-hydrogen peroxide-nitrite system promotes lipid peroxidation of low-density lipoprotein. FEBS Lett. 455, 243-246.
21. Rubbo, H., Radi, R., Trujillo, M., Telleri, R., Kalyanaraman, B., Barnes, S., Kirk, M., and Freeman, B. A. (1994) Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation. Formation of novel nitrogen-containing oxidized lipid derivatives. J. Biol. Chem. 269, 26066-26075.
22. Pryor, W. A., Lightsey, J. W., and Church, D. F. (1982) Reaction of nitrogen dioxide with alkenes and polyunsaturated fatty acids: addition and hydrogen abstraction mechanism. J. Am. Chem. Soc. 104, 6685-6692.
23. Gallon, A. A., and Pryor, W. A. (1994) The reaction of low levels of nitrogen dioxide with methyl linoleate in the presence and absence of oxygen. Lipids 29, 171-176.
24. Laskey, R. E., and Mathews, W. R. (1996) Nitric oxide inhibits peroxynitrite-induced production of hydroxyeicosatetraenoic acids and F2-isoprostanes in phosphatidylcholine liposomes. Arch. Biochem. Biophys. 330, 193-198.
25. Hogg, N., and Kalyanaraman, B. (1999) Nitric oxide and lipid peroxidation. Biochim. Biophys. Acta 1411, 378-384.
26. Rubbo, H. (1998) Nitric oxide and peroxynitrite in lipid peroxidation. Medicina 58, 361-366.
27. Rubbo, H., Parthasarathy, S., Barnes, S., Kirk, M., Kalyanaraman, B., and Freeman, B. A. (1995) Nitric oxide inhibition of lipoxygenase-dependent liposome and low-density lipoprotein oxidation: termination of radical chain propagation reactions and formation of nitrogen-containing oxidized lipid derivatives. Arch. Biochem. Biophys. 324, 15-25.
28. O'Donnell, V. B., Chumley, P. H., Hogg, N., Bloodsworth, A., Darley-Usmar, V. M., and Freeman, B. A. (1997) Nitric oxide inhibition of lipid peroxidation: kinetics of reaction with lipid peroxyl radicals and comparison with alpha-tocopherol. Biochemistry 36, 15216-15223.
29. Rubbo, H., and Freeman, B. A. (1996) Nitric oxide regulation of lipid oxidation reactions: formation and analysis of nitrogen-containing oxidized lipid derivatives. Methods Enzymol. 269, 385-394.
30. Gallon, A. A., and Pryor, W. A. (1993) The identification of the allylic nitrite and nitro derivatives of methyl linoleate and methyl linolenate by negative chemical ionization mass spectroscopy. Lipids 28, 125-133.
31. Pryor, W. A., Castle, L., and Church, D. F. (1985) Nitrosation of organic hydroperoxides by nitrogen dioxide/dinitrogen tetraoxide. J. Am. Chem. Soc. 107, 211-217.
32. Lim, D. G., Sweeney, S., Bloodsworth, A., White, C. R., Chumley, P. H., Krishna, N. R., Schopfer, F., O'Donnell, V. B., Eiserich, J. P., and Freeman, B. A. (2002) Nitrolinoleate, a nitric oxide-derived mediator of cell function: synthesis, characterization, and vasomotor activity. Proc. Natl. Acad. Sci. U.S.A. 99, 15941-15946.
33. Nicolescu, A. C., Zavorin, S. I., Turro, N. J., Reynolds, J. N., and Thatcher, G. R. (2002) Inhibition of lipid peroxidation in synaptosomes and liposomes by nitrates and nitrites. Chem. Res. Toxicol. 15, 985-998.
34. Maragos, C. M., Morley, D., Wink, D. A., Dunams, T. M., Saavedra, J. E., Hoffman, A., Bove, A. A., Isaac, L., Hrabie, J. A., and Keefer, L. K. (1991) Complexes of NO with nucleophiles as agents for the controlled biological release of nitric oxide. Vasorelaxant effects. J. Med. Chem. 34, 3242-3247.
35. Barclay, L. R., Vinqvist, M. R., Mukai, K., Goto, H., Hashimoto, Y., Tokunaga, A., and Uno, H. (2000) On the antioxidant mechanism of curcumin: classical methods are needed to determine antioxidant mechanism and activity. Org. Lett. 2, 2841-2843.
36. Barclay, L. R. C., Locke, S. J., MacNeil, J. M., and VanKessel, J. (1985) Quantitative studies of the autoxidation of linoleate monomers sequestered in phosphatidylcholine bilayer. Absolute rate constants in bilayer. Can. J. Chem. 63, 2633-2638.
37. Buckell, F., Hartry, J. D., Rajalingam, U., Bennett, B. M., Whitney, R. A., and Thatcher, G. R. (1994) Hydrolysis of Nitrite Esters: Putative Intermediates in the Biotransformation of Organic Nitrates. J. Chem. Soc., Perkin Trans. 2, 401-403.
38. Artz, J. D., and Thatcher, G. R. (1998) NO release from NO donors and nitrovasodilators: comparisons between oxyhemoglobin and potentiometric assays. Chem. Res. Toxicol. 11, 1393-1397.
39. Artz, J. D., Toader, V., Zavorin, S. I., Bennett, B. M., and Thatcher, G. R. (2001) In vitro activation of soluble guanylyl cyclase and nitric oxide release: a comparison of NO donors and NO mimetics. Biochemistry 40, 9256-9264.
40. Braughler, J. M., Duncan, L. A., and Chase, R. L. (1986) The involvement of iron in lipid peroxidation. Importance of ferric-to-ferrous ratios in initiation. J. Biol. Chem. 261, 10282-10289.
41. Schafer, F. Q., Qian, S. Y., and Buettner, G. R. (2000) Iron and free radical oxidations in cell membranes. Cell. Mol. Biol. 46, 657-662.
42. Minotti, G., and Aust, S. D. (1992) Redox cycling of iron and lipid peroxidation. Lipids 27, 219-226.
43. Goss, S. P., Hogg, N., and Kalyanaraman, B. (1995) The antioxidant effect of spermine NONOate in human low-density lipoprotein. Chem. Res. Toxicol. 8, 800-806.
44. Rikans, L. E., and Hornbrook, K. R. (1997) Lipid peroxidation, antioxidant protection and aging. Biochim. Biophys. Acta 1362, 116-127.
45. Gutteridge, J. M., and Halliwell, B. (1990) The measurement and mechanism of lipid peroxidation in biological systems. Trends Biochem. Sci. 15, 129-135.
46. Liu, J., Yeo, H. C., Doniger, S. J., and Ames, B. N. (1997) Assay of aldehydes from lipid peroxidation: gas chromatography-mass spectrometry compared to thiobarbituric acid. Anal. Biochem. 245, 161-166.
47. Barclay, L. R., and Vinqvist, M. R. (1994) Membrane peroxidation: inhibiting effects of water-soluble antioxidants on phospholipids of different charge types. Free Radical Biol. Med. 16, 779-788.
48. Barclay, L. R. C., Baskin, K. A., Kong, D., and Locke, S. J. (1987) Autoxidation of model membrane. The kinetics and mechanism of autoxidation of mixed phospholipid bilayer. Can. J. Chem. 65, 2541-2549.
49. Barclay, L. R. C., Baskin, K. A., Locke, S. J., and Schaefer, T. D. (1987) Benzophenone-photosensitized autoxidation of linoleate in solution and sodium dodecyl sulfate micelles. Can. J. Chem. 65, 2529-2540.
50. Lu, J. M., Wittbrodt, J. M., Wang, K., Wen, Z., Schlegel, H. B., Wang, P. G., and Cheng, J. P. (2001) NO affinities of s-nitrosothiols: a direct experimental and computational investigation of RS-NO bond dissociation energies. J. Am. Chem. Soc. 123, 2903-2904.
51. Bartberger, M. D., Mannion, J. D., Powell, S. C., Stamler, J. S., Houk, K. N., and Toone, E. J. (2001) S-N dissociation energies of S-nitrosothiols: on the origins of nitrosothiol decomposition rates. J. Am. Chem. Soc. 123, 8868-8869.
52. Mooradian, D. L., Hutsell, T. C., and Keefer, L. K. (1995) Nitric oxide (NO) donor molecules: effect of NO release rate on vascular smooth muscle cell proliferation in vitro. J. Cardiovasc. Pharmacol. 25, 674-678.
53. Barclay, L. R. C., Baskin, K. A., Dakin, K. A., Locke, S. J., and Vinqvist, M. R. (1990) The antioxidant activities of phenolic antioxidants in free radical peroxidation of phospholipid membrane. Can. J. Chem. 68, 2258-2269.
54. Dikalov, S., Kirilyuk, I., and Grigor'ev, I. (1996) Spin trapping of O-, C-, and S-centered radicals and peroxynitrite by 2H-imidazole-1-oxides. Biochem. Biophys. Res. Commun. 218, 616-622.
55. Foti, M. C., Johnson, E. R., Vinqvist, M. R., Wright, J. S., Barclay, L. R., and Ingold, K. U. (2002) Naphthalene diols: a new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals. J. Org. Chem. 67, 5190-5196.
56. 2 〈=〉 RXONO (X=O, S) rearrangement, a reaction of potential bilogical significance. Can. J. Chem. 73, 1627-1638.
57. Zhang, D., Zhang, R., Park, J., and North, S. W. (2002) Hydroxy peroxy nitrites and nitrates from OH initiated reactions of isoprene. J. Am. Chem. Soc. 124, 9600-9605.
58. Xian, M., Zhu, X. Q., Lu, J., Wen, Z., and Cheng, J. P. (2000) The first O-NO bond energy scale in solution: heterolytic and homolytic cleavage enthalpies of O-nitrosyl carboxylate compounds. Org. Lett. 2, 265-268.
59. Bennett, B. M., McDonald, B. J., Nigam, R., and Simon, W. C. (1994) Biotransformation of organic nitrates and vascular smooth muscle cell function. Trends Pharmacol. Sci. 15, 245-249.
60. Kowaluk, E. A., and Fung, H. L. (1991) Vascular nitric oxide-generating activities for organic nitrites and organic nitrates are distinct. J. Pharmacol. Exp. Ther. 259, 519-525.
61. van der Vliet, A., Eiserich, J. P., Halliwell, B., and Cross, C. E. (1997) Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. A potential additional mechanism of nitric oxide- dependent toxicity. J. Biol. Chem. 272, 7617-7625.
62. Sampson, J. B., Ye, Y., Rosen, H., and Beckman, J. S. (1998) Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch. Biochem. Biophys. 356, 207-213.
63. Giamalva, D. H., Kenion, G. B., Church, D. F., and Pryor, W. A. (1987) Rates and mechanism of reaction of nitrogen dioxide with alkenes in solutions. J. Am. Chem. Soc. 109, 7059-7063.
64. O'Donnell, V. B., Eiserich, J. P., Chumley, P. H., Jablonsky, M. J., Krishna, N. R., Kirk, M., Barnes, S., Darley-Usmar, V. M., and Freeman, B. A. (1999) Nitration of unsaturated fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide, and nitronium ion. Chem. Res. Toxicol. 12, 83-92.
65. O'Donnell, V. B., Eiserich, J. P., Bloodsworth, A., Chumley, P. H., Kirk, M., Barnes, S., Darley-Usmar, V. M., and Freeman, B. A. (1999) Nitration of unsaturated fatty acids by nitric oxide-derived reactive species. Methods Enzymol. 301, 454-470.
66. Goss, S. P., Singh, R. J., Hogg, N., and Kalyanaraman, B. (1999) Reactions of *NO, *NO2 and peroxynitrite in membranes: physiological implications. Free Radical Res. 31, 597-606.
67. Keefer, L. K., Nims, R. W., Davies, K. M., and Wink, D. A. (1996) "NONOates" (1-substituted diazen-l-ium-1,2-diolates) as nitric oxide donors: convenient nitric oxide dosage forms. Methods Enzymol. 268, 281-293.
68. Fitzhugh, A. L., and Keefer, L. K. (2000) Diazeniumdiolates: pro-and antioxidant applications of the "NONOates". Free Radical Biol. Med. 28, 1463-1469.
69. Hogg, N., Struck, A., Goss, S. P., Santanam, N., Joseph, J., Parthasarathy, S., and Kalyanaraman, B. (1995) Inhibition of macrophage-dependent low-density lipoprotein oxidation by nitric-oxide donors. J. Lipid Res. 36, 1756-1762.
70. Goss, S. P., Kalyanaraman, B., and Hogg, N. (1999) Antioxidant effects of nitric oxide and nitric oxide donor compounds on low-density lipoprotein oxidation. Methods Enzymol. 301, 444-453.
71. Williams, D. L. H. (1996) The mechanism of nitric oxide formation from S-nitrosothiols (thionitrites). Chem. Commun. 1085-1091.
72. Cooper, C. E. (1999) Nitric oxide and iron proteins. Biochim. Biophys. Acta 1411, 290-309.
73. Doyle, M. P., LePoire, D. M., and Pickering, R. A. (1981) Oxidation of hemoglobin and myoglobin by alkyl nitrites. Inhibition By Oxygen. J. Biol. Chem. 256, 12399-12404.
74. Oh, S. M. N. Y. F., and Williams, D. L. (1991) Nitrosation by alkyl nitrites. Part 7. Comparison with thionitrites: reactions with phenols. J. Chem. Soc., Perkin Trans. 2, 685-688.
75. Iglesias, E., Garcia Rio, L., Leis, J. R., Pena, M. E., and Williams, D. L. H. (1992) Evidence for concerted acid hydrolysis of alkyl nitrites. J. Chem. Soc. Perkin Trans. 2, 1673-1679.
76. Williams, D. L. H. (1988) Nitrosation, p 214, Cambridge University Press, Cambridge, New York, Melbourne.
77. Patel, H. M. S., and Williams, D. L. H. (1989) Nitrosation by alkyl nitrites. Part 3. Reactions with cysteine in water in the pH range 6-13. J. Chem. Soc., Perkin Trans. 2 339-341.
78. Kochi, J. K. (1973) Free radicals. In Reactive Intermediates in Organic Chemistry (Olah, G. A., Ed.) p 906, John Wiley & Sons, New York.
79. Nussbaum, A. L., and Robinson, C. H. (1962) Recent developments in the preparative photolysis of organic nitrites. In Tetrahedron 17, 35-39.
80. Barton, D. H. R., Hesse, R. H., Pechet, M. M., and Smith, L. C. (1979) The mechanism of the Barton reaction. J. Chem. Soc., Perkin Trans. 1 1159-1165.
81. Grossi, L., and Strazzari, S. (1999) A New Synthesis of Alkyl Nitrites: The Reaction of Alkyl Alcohols with Nitric Oxide in Organic Solvents. J. Org. Chem. 64, 8076-8079.
82. Grossi, L. (1997) The photolysis of cycloalkyl nitrite esters: the radical intermediates as studied by EPR. Tetrahedron 53, 6401-6410.
83. Grossi, L. (1997) The photoinduced ring expansion of five membered ring nitrites: a 1,6-exo ring closure process of the intermediate 5-nitrosopentanoyl-type radical. Tetrahedron 53, 3205-3214.