Organic Nitrates and Nitrites

Nitric Oxide Donors: For Pharmaceutical and Biological Applications

Volumn , Issue , 2005, Pages 33-54

  Harrison, Roger ^a  

^a University of Bath   (United Kingdom)

Author keywords

Chemical reaction between organic nitrates and thiols; Cytochrome P 450 dependent systems; Glutathione S transferase; Organic nitrates; Organic nitrites

Indexed keywords

EID: 84889836595     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527603751.ch2     Document Type: Chapter

References (128)

1. Murell, W., Nitroglycerin as a remedy for angina pectoris. Lancet i (1879), p. 80-81
2. Ahlner, J., Andersson, R. G. G., Torfgard, K., Axelsson, K. L., Organic nitrate esters: clinical use and mechanisms of actions. Pharmacol. Rev. 43 (1991), p. 351-423
3. Parker, J. D., Parker, J. O., Nitrate therapy for stable angina pectoris. New Engl. J. Med. 338 (1998), p. 520-531
4. Brunton, T., On the use of nitrite of amyl in angina pectoris. Lancet ii (1867), p. 97-98
5. Lembo, N. J., Dell-Italia, L. J., Crawford, M. H., Bedside diagnosis of systolic murmurs. New Engl. J. Med. 318 (1988), p. 1572-1578
6. Holland, M. A., Kozlowski, L. M., Clinical features and management of cyanide poisoning. Clin. Pharmacol. 5 (1986), p. 737-741
7. Sigell, L.T., Kapp, F.T., Nelson, E. D., Falck, R. S., Popping and snorting volatile nitrites: A current fad for getting high. Am. J. Psychiatry. 135 (1978), p. 1216-1218
8. Goedert, J. J., Recreational drugs: Relationship to AIDS. Ann. N.Y. Acad. Sci. 437 (1984), p. 192-199
9. Haverkos, H.W., Dougherty, J., Health hazards of nitrite inhalants. Am. J. Med. 84 (1988), p. 479-482
10. Murad, F., Mittal, C. K., Arnold, W. P., Katsuki, S., Kimura, H., Guanylate cyclase: activation by azide, nitro compounds, nitric oxide, and hydroxyl radical and inhibition by hemoglobin and myoglobin. Adv. Cyclic Nucleotide Res. 9 (1978), p. 145-158
11. Ignarro, L. J., Lippton, H., Edwards, J. C., Baricos, W. H., Hyman, A. L., Kadowitz, P. J., Gruetter, C. A., Mechanism of vascular smooth muscle relaxation by organic nitrates, nitrites, nitroprusside, and nitric oxide: evidence for the involvement of S-nitrosothiols as active intermediates. J. Pharmacol. Exp. Ther. 218 (1981), p. 739-749
12. Mangione, N. J., Glasser, S. P., Phenomenon of nitrate tolerance. Am. Heart J. 128 (1994), p. 137-146
13. Abrams, J., Elkayam, U., Thadani, U., Fung, H-L., Tolerance: An historical overview. Am. J. Cardiol. 81 (1998), p. 3A-14A
14. Needleman, P., Krantz, J. C., The biotransformation of nitroglycerin. Biochem. Pharmacol. 14 (1965), p. 1225-1230
15. Needleman, P., Blehm, D J., Rotskoff, K. S., Relationship between glutathione-dependent denitration and the vasodilator effectiveness of organic nitrates. J. Pharmacol. Exp. Ther. 237 (1969), p. 296-288
16. Needleman, P., Blehm, D. J., Harkey, A. B., Johnson, E. M., Lang, S., The metabolic pathway in the degradation of glyceryl trinitrate. J. Pharmacol. Exp. Ther. 179 (1971), p. 347-353
17. Needleman, P., Johnson, E. M., J. Pharmacol. Exp. Ther. 184 (1973), p. 709-715
18. Ignarro, L. J., Gruetter, C. A., Requirement of thiols for activation of coronary arterial guanylate cyclase by glycerol trinitrate and sodium nitrite: Possible involvement of S-nitrosothiols. Biochim. Biophys. Acta 631 (1980), p. 221-231
19. Kowaluk, E., Poliszuk, R., Fung. H-L., Tolerance to relaxation in rat aorta: comparison of an S-nitrosothiol with nitroglycerin. Eur. J. Pharmacol. 144 (1987), p. 379-383
20. Kowaluk, E. A., Fung, H-L., Spontaneous liberation of nitric oxide cannot account for in vitro vascular relaxation by S-nitrosothiols. J. Pharmacol. Exp. Ther. 255 (1990), p. 1256-1264
21. Butler, A. R., Flitney, F.W., Williams, D. L. H., NO, nitrosonium ions, nitrosothiols and iron-nitrosyls in biology: a chemist's perspective. Trends in Pharmacol. Sci. 16 (1995), p. 18-22
22. Arnold, W. P., Mittal, C. K., Katsuki, S., Murad, F., Proc. Natl. Acad. Sci. USA. 74 (1977), p. 3203-3207
23. Fung, H-L., Chung, S. J., Bauer, J. A., Chong, S., Kowaluk, E. A., Biochemical mechanism of organic nitrate action. Am. J. Cardiol. 70 (1992), p. 4B-10B
24. Zweier, J. L., Samouilov, A., Kuppusamy, P., Non-enzymatic nitric oxide synthesis in biological systems. Biochim. Biophys. Acta 1411 (1999), p. 250-262
25. Bennett, B. M., Marks, G. S., How does nitroglycerin induce vascular smooth muscle relaxation? Trends in Pharmacol. Sci. (1984), p. 329-332
26. Benjamin, N., Dutton, J. A. E., Ritter, J. M., Human vascular smooth muscle cells inhibit platelet aggregation when incubated with glyceryl trinitrate: evidence for generation of nitric oxide. Br. J. Pharmacol. 102 (1991), p. 847-850
27. Feelisch, M., Kelm, M., Biotransformation of organic nitrates to nitric oxide by vascular smooth muscle and endothelial cells. Biochem. Biophys. Res. Commun. 180 (1991), p. 286-293
28. Salvemini, D., Mollace, V., Pistelli, A., Anggard, E., Vane, J., Metabolism of glyceryl trinitrate to nitric oxide by endothelial cells and smooth muscle cells and its induction by E. coli lipopolysaccharide. Proc. Natl. Acad. Sci. USA 89 (1992), p. 982-986
29. Feelisch, M., Noack, M., Correlation between nitric oxide formation during degradation of organic nitrates and activation of guanylate cyclase. Eur. J. Pharmacol. 139 (1987), p. 19-30
30. Feelisch, M., Noack, M., Nitric oxide (NO) formation from nitrovasodilators occurs independently of hemoglobin or non-heme iron. Eur. J. Pharmacol. (1987), 142, p. 465-469
31. Thatcher, G. R. J., Weldon, H., NO problem for nitroglycerin: organic nitrate chemistry and therapy. Chem. Soc. Rev. (1998), 27, p. 331-337
32. Artz, J. D., Yang, K., Lock, J., Sanchez, C., Bennett, B. M., Thatcher, G. R. J., Reactivity of thionitrate esters: putative intermediates in nitrovasodilator activity. Chem. Commun. (1996), p. 927-928
33. Chong, S., Fung, H-L., Biochemical and pharmacological interactions between nitroglycerin and thiols. Effects of thiol structure on nitric oxide generation and tolerance reversal. Biochem. Pharmacol. 42 (1993), p. 1433-1439
34. Artz, J. D., Toader, V., Zavorin, S. I., Bennett, B. M., Thatcher, G. R. J., In vitro activation of soluble guanyl cyclase and nitric oxide release: a comparison of NO donors and NO mimetics Biochemistry 40 (2001), p. 9256-9264
35. Artz, J. D., Schmidt, B., McCracken, J. L., Marletta, M. A., Effects of nitroglycerin on soluble guanylate cyclase. J. Biol. Chem. 277 (2002), p. 18253-18256
36. Harrison, D. G., Bates, J. N., The nitrovasodilators. New ideas about old drugs. Circulation 87 (1993), p. 1461-1467
37. Needleman, P., Harkey. A. B., Role of endogenous glutathione in the metabolism of glyceryl trinitrate by isolated perfused rat liver. Biochem. Pharmacol. 20 (1971), p. 1867-1876
38. Habig, W. H., Keen, J. H., Jakoby, W. B., Glutathione S-transferases in the formation of cyanide from organic thiocyanates and as an organic nitrate reductase. Biochem. Biophys. Res. Commun. 64 (1975), p. 501-506
39. Keen, J. H., Habig, W. H., Jakoby, W. B., Mechanism for the several activities of the glutothione S-transferases. J.Biol. Chem. 251 (1976), p. 6183-6188
40. Lau, D. T. W., Benet, L. Z., Nitroglycerin metabolism in subcellular fractions of rabbit liver. Dose dependency of glyceryl dinitrate formation and possible involvement of multiple isoenzymes of glutathione S-transferases. Drug Metab. Dispos. 18 (1990), p. 292-297
41. Tsuchida, S., Maki, T., Sato, K., Purification and characterization of glutathione transferases with an activity toward nitroglycerin from human aorta and heart. J. Biol. Chem. 265 (1990), p. 7150-7157
42. Tahir, M. K., Guthenberg, C., Mannevik, B., Inhibitors for distinction of three types of human glutathione transferase. FEBS Lett. 181 (1985), p. 249-252
43. Yeates, R. A., Schmid, M., Leithold, M., Antagonism of glycerol trinitrate activity by an inhibitor of glutathione S-transferase. Biochem. Pharmacol. 38 (1989), p. 1749-1753
44. Gruetter, C. A., Lemke, S. M., Dissociation of cysteine and glutathione levels from nitroglycerin-induced relaxation. Eur. J. Pharmacol. 111 (1985), p. 85-95
45. Sakanashi, M., Matsuzaki, T., Aniya, Y., Nitroglycerin relaxes coronary artery of the pig with no change in glutathione content or glutathione-S-transferase activity. Br. J. Pharmacol. 103 (1991), p. 1905-1908
46. Salvemini, D., Pistelli, A., Vane, J., Conversion of glyceryl trinitrate to nitric oxide in tolerant and non-tolerant smooth muscle and endothelial cells. Br. J. Pharmacol. 108 (1993), p. 162-169
47. Chung, S-J., Fung, H-L., Relationship between nitroglycerin-induced vascular relaxation and nitric oxide production. Probes with inhibitors and tolerance development. Biochem. Pharmacol. 45 (1993), p. 157-163
48. Hill, K. E., Hunt, R.W., Jones, R., Hoover, R. L., Burk, R. F., Metabolism of nitroglycerin by smooth muscle cells. Involvement of glutathione and glutathione S-transferase. Biochem. Pharmcol. 43 (1992), p. 561-566
49. Kurz, M. A., Boyer, T. D., Whalen, R., Peterson, T. E., Harrison, D. G., Nitroglycerin metabolism in vascular tissue: role of glutathione transferases and relationship between NO and NO2 formation. Biochem. J. 292 (1993), p. 545-550
50. Romanin, C., Kukovetz, W. R., Guanylate cyclase activation by organic nitrates is not mediated via nitrite. J. Mol. Cell Cardiol. 20 (1988), p. 389-396
51. Parks, N. J., Krohn, K. A., Mathis, C. A., Chasko, J. H., Geiger, K. R., Gregor, M. E., Peck, N. F., Science 212 (1981), p. 58-61
52. Servent, D., Delaforge, M., Ducrocq, C., Mansuy, D., Lenfant, M., Nitric oxide formation during microsomal hepatic denitration of glyceryl trinitrate: involvement of cytochrome P-450. Biochem. Biophys. Res. Commun. 163 (1989), p. 1210-1216
53. Schroeder, H., Schroer, K., Inhibitors of cytochrome P-450 reduce cyclic GMP stimulation by glyceryl trinitrate in LLC-PK1 kidney epithelial cells. Naunyn Schmiedebergs Arch. Pharmacol. 342 (1990), p. 616-618
54. Bornfeldt, K. E., Axelsson, K. L., Studies on the effect of different inhibitors of arachidonic acid metabolism on glyceryl trinitrite-induced relaxation and cGMP elevation in bovine vascular tissue. Pharmacol. Toxicol. 60 (1987), p. 110-116
55. Serabjit-Singh, C. J., Nishio, S. J., Philpot, R. M., Plopper, C. G., The distribution of cytochrsome P450 monooxygenase in cells in the rabbit lung: an ultrastructural immunocytochemical characterization. Mol. Pharmacol. 33 (1988), p. 279-289
56. Pinto, A., Abraham, N. G., Mullane, K. M., Cytochrome P450-dependent monoxygenase activity and endothelial-dependent relaxations induced by arachidonic acid. J. Pharmacol. Exp. Ther. 236 (1986), p. 445-451
57. MacDonald, B.J., Bennett. B.M., Cytochrome P-450 mediated biotransformation of organic nitrates. Can. J. Physiol. Pharmacol. 68 (1990), p. 1552-1557
58. MacDonald, B. J., Bennett, B. M., Biotransformation of glyceryl trinitrate by rat aortic cytochrome P450. Biochem. Pharmacol. 45 (1993), p. 268-270
59. Bennett, B. M., MacDonald, B. J., St. James, M. J., Hepatic cytochrome P-450-mediated activation of rat aortic guanyl cyclase. J. Pharmacol. Exp. Ther. 261 (1992), p. 716-723
60. Schroeder, H., Leitman, D. C., Hayward, L. D., Bennett, B. M., Murphy, F., Cultured rat lung fibroblasts as a model for organic nitrate-induced cyclic GMP accumulation and activation of guanylate cyclase. J. Appl. Cardiol. 2 (1987), p. 301-311
61. Schroeder, H., Cytochrome P-450 mediates bioactivation of organic nitrates. J. Pharmacol Exp. Ther. 262 (1992), p. 298-302
62. Bennett, B. M., MacDonald, B. J., Nigam, R., Long, P. G., Simon, W. C., Inhibition of nitrovasodilator- and acetylcholine-induced relaxation and cyclic GMP accumulation by the cytochrome P450 substrate 7-ethoxyresorufin. Can. J. Physiol. Pharmacol. 70 (1992), p. 1297-1303
63. Liu, Z., Brien, J. F., Marks, G. S., McLaughlin, B. E., Nakatsu, K., Lack of evidence for the involvement of cytochrome P450 or other hemoproteins in metabolic activation of glyceryl trinitrate in rabbit aorta. J. Pharmacol. Exp. Ther. 264 (1993), p. 1432-1438
64. Minamiyama, Y., Takemura, S., Akiyama, T., Imaoka, S., Inoue, M., Funae, Y., Okada, S., Isoforms of cytochrome P-450 on organic nitrate-derived nitric oxide release in human heart vessels. FEBS Lett. 452 (1999), p. 165-169
65. McGuire, J., Anderson, D. J., MacDonald, B. J., Narayanasami, R., Bennett, B. M., Inhibition of NADPH-cytochrome P450 reductase and glyceryl trinitrate biotransformation by diphenyleneiodonium sulfate. Biochem. Pharmacol. 56 (1998), p. 881-893
66. Chung, S-J., Fung, H-L., Identification of the subcellular site for nitroglycerin metabolism to nitric oxide in bovine coronary smooth muscle cells. J. Pharmacol. Exp. Ther. 253 (1990), p. 614-619
67. Chung, S-J., Fung, H-L., A common enzyme may be responsible for the conversion of organic nitrates to nitric oxide in vascular microsomes. Biochem. Biophys. Res. Commun. 185 (1992), p. 932-937
68. Chung, S-J., Chong, S., Seth, P., Jung, C. Y., Fung, H-L., Conversion of nitroglycerin to nitric oxide in microsomes of the bovine coronary artery smooth muscle is not primarily mediated by glutathione S-transferases. J. Pharmacol.Exp. Ther. 260 (1992), p. 652-659
69. Kowaluk, E. A., Fung, H-L., Vascular nitric oxide-generating activities for organic nitrites and organic nitrates are distinct. J. Phamacol. Exp. Ther. 259 (1991), p. 519-525
70. Seth, P., Fung, H-L., Biochemical characterization of a membrane-bound enzyme responsible for generating nitric oxide from nitroglycerin in vascular smooth muscle cells. Biochem. Pharmacol. 46 (1993), p. 1481-1486
71. Massey, V., Harris, C. M., Milk xanthine dehydrogenase: the first one hundred years. Biochem. Soc. Trans. 25 (1997), p. 750-755
72. Hille, R., The mononuclear molybdenum enzymes. Chem.Rev. 96 (1996), p. 2757-2816
73. Harrison, R., Structure and function of xanthine oxidoreductase: where are we now? Free Radical Biol. Med. 33 (2002), p. 774-797
74. Krenitsky, T. A., Neil, S. M., Elion, G. B., Hichins, G. H., A comparison of the specificities of xanthine oxidase and aldehyde oxidase. Arch. Biochem. Biophys. 150 (1972), p. 585-599
75. Saito, T., Nishino, T., Differences in redox and kinetic properties between NAD-dependent and O2-dependent types of rat liver xanthine dehydrogenase. J. Biol. Chem. 264 (1989), p. 10015-10022
76. Westerfield, W. W., Richert, D. A., Higgins, E. S., Further studies with xanthine oxidase inhibitors. J. Biol. Chem. 234 (1959), p. 1897-1900
77. Fridovich, I., Handler, P., Xanthine oxidase. V. Differential inhibition of the reduction of various electron acceptors. J. Biol. Chem. 237 (1962), p. 916-921
78. Hackenthal, E., Hackenthal, R., Kompetitive inhibitoren der nitratereduktion durch xanthinoxydase. Naturwissenschaften 53 (1966), p. 81
79. Sergeev, N. S., Ananiadi, L. I., Lvov, P., Kretovich, W. L., The nitrate reductase activity of milk xanthine oxidase. J. Appl. Biochem. 7 (1985), p. 86-92
80. Millar, T. M., Stevens, C. R., Benjamin, N., Eisenthal, R., Harrison, R., Blake, D. R., Xanthine oxidoreductase catalyses the reduction of nitrates and nitrite to nitric oxide under hypoxic conditions. FEBS Lett. 427 (1998), p. 225-228
81. Doel, J. J., Godber, B. L. J., Eisenthal, R., Harrison, R., Reduction of organic nitrates catalyzed by xanthine oxidoreductase under anaerobic conditions. Biochim. Biophys. Acta 1527 (2001), p. 91-87
82. Millar, T. M., Stevens, C. R., Blake, D. R., Xanthine oxidase can generate nitric oxide from nitrate in ischaemia. Biochem. Soc. Trans. 25 (1997), p. 528S
83. Zhang, Z., Naughton, D. P., Blake, D. R., Benjamin, N., Stevens, C. R., Winyard, P. G., Symons, M. C. R., Harrison, R., Human xanthine oxidase converts nitrite ions into nitric oxide. Biochem. Soc. Trans. 25 (1997), p. 524S
84. Zhang, Z., Naughton, D., Winyard, P. G., Benjamin, N., Blake, D. R., Symons, M. C. R., Generation of nitric oxide by a nitrite reductase activity of xanthine oxidase: a potential pathway for nitric oxide formation in the absence of nitric oxide synthase activity. Biochem. Biophys. Res. Commun. 249 (1998), p. 767-772
85. Godber, B. L. J., Doel, J. J., Sapkota, G. P., Blake, D. R., Stevens, C. R., Eisenthal, R., Harrison, R., Reduction of nitrite to nitric oxide catalyzed by xanthine oxidoreductase. J. Biol. Chem. 275 (2000), p. 7757-7763
86. Doel, J. J., Godber, B. L. J., Goult, T. A., Eisenthal, R., Harrison, R., Reduction of organic nitrites to nitric oxide catalysed by xanthine oxidase: possible role in metabolism of nitrovasodilators. Biochem. Biophys. Res. Commun. 270 (2000), p. 880-885
87. Sanders, S. A., Eisenthal, R., Harrison, R., NADH oxidase activity of human xanthine oxidoreductase: Generation of superoxide anion. Eur. J. Biochem. 245 (1997), p. 541-548
88. Godber, B. L. J., Doel, J. J., Goult, T. A., Eisenthal, R., Harrison, R., Suicide inactivation of xanthine oxidoreductase during reduction of inorganic nitrite to nitric oxide. Biochem. J. 358 (2001), p. 325-333
89. Wong, P. S-Y., Fukuto, J. M., Reaction of organic nitrate esters with reduced flavins: a possible mechanism of bioactivation. Drug Metab. Dispos. 27 (1999), p. 502-509
90. O'Byrne, S., Shirodaria, C., Millar, T., Stevens, C., Blake, D., Benjamin, N., Inhibition of platelet aggregation with glyceryl trinitrate and xanthine oxidoreductase. J. Pharmacol. Exp. Ther. 292 (2000), p. 326-330
91. Ratz, J. D., McGuire, J. J., Anderson, D. J., Bennett, B. M., Effects of the flavoprotein inhibitor, diphenylene iodonium sulfate, on ex vivo organic nitrate tolerance in the rat. J. Pharmacol. Exp. Ther. 293 (2000), p. 569-577
92. Rouquette, M., Page, S., Bryant, R., Benboubetra, M., Stevens, C. R., Blake, D. R., Whish, W. J. D., Harrison, R., Tosh, D., Xanthine oxidoreductase is asymmetrically localised on the outer surface of human endothelial and epithelial cells in culture. FEBS Lett. 426 (1998), p. 397-401
93. Vickers, S., Schiller, H. J., Hildreth, J. E., Bulkley, G. B., Immunoaffinity localization of the enzyme xanthine oxidase on the outside surface of endothelial cell plasma membrane. Surgery 124 (1998), p. 551-560
94. Trujillo, M., Alvarez, M. N., Peluffo, G., Freeman, B. A., Radi, R., Xanthine oxidase-mediated decomposition of S-nitrosothiols. J. Biol. Chem. 273 (1998), p. 7828-7834
95. Chen, Z., Zhang, J., Stamler, J. S., Identification of the enymatic mechanism of nitroglycerin bioactivation. Proc. Natl. Acad. Sci. USA 99 (2002), p. 8306-8311
96. Ignarro, L. J., After 130 years, the molecular mechanism of action of nitroglycerin is revealed. Proc. Natl. Acad. Sci. USA 99 (2002), p. 7816-7817
97. Brien, J. F., McLaughlin, B. E., Kobus, S. M., Kawamoto, J. H., Nakatsu, K., J. Pharmacol. Exp. Ther. 244 (1988), p. 322-327
98. Kawamoto, J. H., McLaughlin, B. E., Brien, J. F., Marks, G. S., Nakatsu, K., Biotransformation of glyceryl trinitrate and elevation of cyclic GMP precede glyceryl trinitrate-induced vasodilation. J. Cardiovasc. Pharmacol. 15 (1990), p. 714-719
99. DiFabio, J., Ji, Y., Vasiliou, V., Thatcher, G. R. J., Bennett, B. M., Role of mitochondrial aldehyde dehydrogenase in nitrate tolerance. Mol. Pharmacol. 64 (2003), p. 1109-1116
100. Needleman, P., Lang, E., Johnson, E. M., Organic nitrates. Relationship between biotransformation and rational angina pectoris therapy. J. Pharmacol. Exp. Ther. 181 (1972), p. 489-497
101. Mayer, B., Bioactivation of nitroglycerin - a new piece in the puzzle. Angew. Chem. Int. Ed. 42 (2003), p. 388-391
102. Boesgaard, S., Aldershvile, J., Poulsen, E., Loft, S., Anderson, M. E., Meister, A., Nitrate tolerance in vivo is not associated with depletion of arteria. or venous thiol levels. Circ. Res. 74 (1994), p. 115-120
103. Fung, H-L., Chong, S., Kowaluk, E., Hough, K., Kakemi, M., Mechanisms for the pharmacological interaction of organic nitrates with thiols. Existence of an extracellular pathway for the reversal of nitrate vascular tolerance by N-acetylcytseine. J. Pharmacol. Exp. Ther. 245 (1988), 524-530
104. Kurz, S., Hink, U., Nickenig, G., Borthayre, A. B., Harrison, D. G., Munzel, T., Evidence for a causal role for the renin-angiotensin system in nitrate tolerance. Circulation 99 (1999), p. 3181-3187
105. Munzel, T., Sayegh, H., Freeman, B. A., Tarpey, M. M., Harrison, D. G., Evidence for enhanced vascular superoxide anion production in nitrate tolerance. A novel mechanism underlying tolerance and cross-tolerance. J. Clin. Invest. 95 (1995), p. 187-194
106. Munzel, T., Hink, U., Yigit, H., Macharzina, R., Harrison, D. G., Mulsch, A., Role of superoxide dismutase in in vivo and in vitro nitrate tolerance. Br. J. Pharmacol. 127 (1999), p. 1224-1230
107. Gori, T., Parker, J. D., Nitrate tolerance. A unifying hypothesis. Circulation 106 (2002), p. 2510-2513
108. Axelsson, K. L., Anderson, R. G. G., Tolerance towards nitroglycerin, induced in vivo, is correlated to a reduced cGMP response and an alteration in cGMP turnover. Eur. J. Pharmacol. 88 (1983), p. 71-79
109. Waldeman, S. A., Rapoport, R. M., Ginsburg, R., Murad, F., Desensitization to nitroglycerin in vascular smooth muscle from rat and human. Biochem. Pharmacol. 35 (1986), p. 3525-3531
110. Mulsch, A., Busse, R., Bassenge. E., Desensitization of guanylate cyclase in nitrate tolerance does not impair endothelium-dependent responses. Eur. J.Pharmacol. 158 (1988), p. 191-198
111. Kowaluk, E. A., Fung, H-L., Dissociation of nitrovasodilator-induced relaxation from cylic GMP levels during in vitro nitrate tolerance. Eur. J. Pharmacol. 176 (1990), p. 91-95
112. Husain, M., Adrie, C., Ichinose, F., Kavosi, M., Zapol, W. M., Circulation 89 (1994), p. 2498-2502
113. Hinz, B., Schroeder, H., Nitrate tolerance is specific for nitric acid esters and its recovery requires an intact protein synthesis. Biochem. Biophys.Res. Commun. 252 (1998), p. 232-235
114. Bohyn, M., Berkenboom, G., Fontaine, J., Effect of nitrate tolerance and dipyridamole on the response to SIN1 in human isolated saphenous vein. Cardiovasc. Drugs. Ther. 5 (1991), p. 457-462
115. Torfgard, K. E., Ahlner, J., Effect of a low dose of dipyridamole on glyceryl trinitrate tolerance in healthy volunteers. J. Cardiovasc. Pharmacol. 21 (1993), p. 516-521
116. Hasegawa, K., Taniguchi, T., Takakura, K., Goto, Y., Muramatsu, I., Possible involvement of nitroglycerin converting step in nitroglycerin tolerance. Life Sci. 64 (1999), p. 2199-2206
117. Ichimori, K., Fukahori, M., Nakazawa, H., Okamoto, K., Nishino, T., Inhibition of xanthine oxidase and xanthine dehydrogenase by nitric oxide. J. Biol. Chem. 274 (1999), p. 7763-7768
118. Saleem, M., Ohshima, H., Xanthine oxidase converts nitric oxide to nitroxyl that inactivates the enzyme. Biochem. Biophys. Res. Commun. 315 (2004), p. 455-462
119. Minamiyama, Y., Takemura, S., Imaoka, S., Funae, Y., Tanimoto, Y., Inoue, M., Irreversible inhibition of cytochrome P450 by nitric oxide. J. Pharmacol. Exp. Ther. 283 (1997), p. 1479-1485
120. McGuire, J. J., Anderson, D. J., Bennett, B. M., Inhibition of the biotransformation and pharmacological actions of glyceryl trinitrate by the flavoprotein inhibitor, diphenyleneiodonium sulfate. J. Pharmacol. Exp. Ther. 271 (1994), p. 708-714
121. Laursen, J. B., Mulsch, S., Boesgaard, S., Mordvintcev, P., Trautner, S., Gruhn, N., Nielsen-Kudsk, J. E., Busse, R., Alsershvile, J., In vivo nitrate tolerance is not associated with reduced bioconversion of nitroglycerin to nitric oxide. Circulation 94 (1996), p. 2241-2247
122. Patel, H.M.S., Williams, D.L.H., J. Chem. Soc. Perkin Trans. 2 (1990), p. 37-42
123. Meyer, D. J., Kramer, H., Ketterer, B., Human glutathione transferase catalysis of the formation of S-nitrosoglutathione from organic nitrites plus glutathione. FEBS Lett. 351 (1994), p. 427-428
124. Akerboom, T. P. M., Ji, Y., Wagner, G., Sies, H., Subunit specificity and organ distribution of glutathione transferase-catalysed S-nitrosoglutathione formation from alkyl nitrites in the rat. Biochem. Phamacol. 53 (1996), p. 117-120
125. Ji, Y., Akerboom, T.P.M., Sies, H., Microsomal formation of S-nitrosoglutathione from organic nitrites: possible role of membrane-bound glutathione transferase. Biochem. J. 313 (1996), p. 377-380
126. Kowaluk, E. A., Fung, H-L., Vascular nitric oxide-generating activities for organic nitrates and nitrites are distinct. J. Pharmacol. Exp. Ther. 259 (1991), p. 519-525
127. Bauer, J. A., Nolan, T., Fung, H-L., Vascular and hemodynamic differences between organic nitrates and nitrites. J. Pharmacol. Exp. Ther. 280 (1997), p. 326-331
128. Kleschyov, A. L., Oelze, M., Daiber, A., Huang, Y., Mollnau, H., Schulz, E., Sydow, K., Fichtlscherer, B., Mulsch, A., Munzel, T., Does nitric oxide mediate the vasodilator activity of nitroglycerin? Circ. Res. 93 (2003), p. e104-e112