Chemistry, analysis, and biological roles of S-nitrosothiols

Analytical Biochemistry

Volumn 249, Issue 1, 1997, Pages 1-9

  Butler, Anthony R ^a   Rhodes, Peter ^b  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b SOUTHAMPTON GENERAL HOSPITAL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CHEMISTRY;

S-NITROSOTHIOLS;

CHEMICAL ANALYSIS;

ANTITHROMBOCYTIC AGENT; GAMMA GLUTAMYLTRANSFERASE; GLYCERYL TRINITRATE; NITRATE; NITRIC OXIDE; NITRITE; NITROSO DERIVATIVE; S NITROSOCYSTEINE; S NITROSOGLUTATHIONE; THIOL DERIVATIVE; VASODILATOR AGENT;

CELL DEATH; CHEMOLUMINESCENCE; CLINICAL TRIAL; DRUG ACTIVITY; HELLP SYNDROME; HUMAN; NONHUMAN; PREECLAMPSIA; PRIORITY JOURNAL; REVIEW; THROMBOCYTE ACTIVATION; VASODILATATION;

EID: 0031570736     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1006/abio.1997.2129     Document Type: Review

References (89)

1. Fontecave, M., and Pierre, J.-L. (1994), Bull. Soc. Chim. Fr. 131, 620-631.
2. Williams, D. L. H. (1988) Nitrosation, pp. 173-180, Cambridge Univ. Press, Cambridge, UK.
3. Field, L., Dilts, R. V., Ravichandran, R., Lenhert, P. G., and Carnahan, G. E. (1978) Chem. Commun., 249-250.
4. Hart, T. W. (1985) Tetrahedron Lett. 26, 2013-2016.
5. Bainbrigge, N., Butler, A. R., and Görbitz, C.-H. (1997) J. Chem. Soc. Perkin Trans. 2, 351.
6. Barrett, J., Fitzgibbons, L. J., Glauser, J., Still, R. H., and Young, P. N. W. (1966) Nature 211, 848.
7. Rheinbolt, H., and Mott, F. (1932) J. Prakt. Chem. 133, 328-332.
8. McAninly, J., Williams, D. L. H., Askew, S. C., Butler, A. R., and Russell, C. (1993) Chem. Commun., 1758-1759.
9. Askew, S. C., Barnett, D. J., McAninly, J., and Williams, D. L. H. (1995) J. Chem. Soc. Perkin Trans. 2, 741-745.
10. Dicks, A. P., Swift, H. R., Williams, D. L. H., Butler, A. R., Al-Sa'doni, H. H., and Cox, B. G. (1996) J. Chem. Soc. Perkin Trans. 2, 481-487.
11. Gordge, M. P., Meyer, D. J., Hothersall, J., Neild, G. H., Payne, N. N., and Noronha-Dutra, A. (1995) Br. J. Pharmacol. 114, 1083-1089.
12. Dicks, A. P., and Williams, D. L. H. (1996) Chem. Biol. 3, 655-659.
13. Gorren, A. C. F., Schrammel, A., Schmidt, K., and Mayer, B. (1996) Arch. Biochem. Biophhys. 330, 219-228.
14. Mellion, B. T., Ignarro, L. J., Meyers, C. B., Ohlstein, E. H., Ballot, B. A., Hyman, A. L., and Kadowitz, P. J. (1983) Mol. Pharmacol. 23, 653-660.
15. Moynihan, H. A., and Roberts, S. M. (1994) J. Chem. Soc. Perkin Trans, 1, 797-805.
16. MacAllister, R. J., Calver, A. L., Riezebos, J., Collier, J., and Vallance, P. (1995) J. Pharmacol. Exp. Ther. 273, 154-160.
17. Mathews, W. R., and Kerr, S. W. (1993) J. Pharmacol. Exp. Ther. 267, 1529-1537.
18. Gaston, B., Drazen, J. M., Jansen, A., Sugarbaker, D. A., Loscalzo, J., Richards, W., and Stamler, J. S. (1994) J. Pharmacol. Exp. Ther. 268, 978-984.
19. Kowaluk, E. A., and Fung, H.-L. (1990) J. Pharmacol. Exp. Ther. 255, 1256-1264.
20. Bauer, J. A., and Fung, H.-L. (1991) J. Pharmacol. Exp. Ther. 256, 249-254.
21. Horowitz, J. D., Antman, E. N., Lorell, B. H., Barry, W. H., and Smith, T. W. (1993) Circulation 68, 1247-1253.
22. Ignarro, L. J., Lippton, H., Edwards, J. C., Baricos, W. H., Hyman, A. L., Kadowitz, P. J., and Gruetter, C. A. (1981) J. Pharmacol. Exp. Ther. 218, 739-749.
23. Palmer, R. M. J., Moncada, S., and Radomski, M. W. (1987) Br. J. Pharmacol., 92, 181-187.
24. Radomski, M. W., Palmer, R. M. J., and Moncada, S. (1987) Br. J. Pharmacol. 92, 639-646.
25. Rubanyi, G. M. (1991) J. Cell. Biochem. 46, 27-36.
26. Salas, E., Moro, M. A., Askew, S. C., Hodson, H. F., Butler, A. R., Radomski, M. W., and Moncada, S. (1994) Br. J. Pharmacol. 112, 1071-1076.
27. Gaston, B., Reilly, J., Drazen, J. M., Fackler, J., Ramdev, P., Arnelle, D., Mullins, M. E., Sugarbaker, D. J., Chee, C., Singel, D. J., Loscalzo, J., and Stamler, J. S. (1993) Proc. Natl. Acad. Sci. USA 90, 10957-10961.
28. Stamler, J. S., Jaraki, O., Osborne, J., Simon, D. I., Keaney, J., Vita, J., Singel, D., Valeri, C. R., and Loscalzo, J. (1992) Proc. Natl. Acad. Sci. USA 89, 7674-7677.
29. Zafiriou, O. C., and McFarland, M. (1980) Anal. Chem. 52, 1662-1667.
30. Hobbs, A. J., Griscavage, J. M., Rogers, N. E., Byrns, R. E., and Ignarro, L. J. (1993) Endothelium S18, 70-75.
31. Archer, S. (1993) FASEB J. 7, 349-368.
32. Knettel, K., and Feelisch, M. (1993)Endothelium S32, 125-129.
33. Kiechle, F. L., and Malinski, T. (1993) Clin. Chem. 100, 567-575.
34. Chung, S.-J., and Fung, H.-L. (1992) Anal. Lett. 25, 2021-2036.
35. Gustafsson, L. E., Leone, A. M., Persson, M. G., Wiklund, N. P., and Moncada, S. (1991) Biochem. Biophys. Res. Commun. 181, 852-857.
36. Stamler, J. S., and Loscalzo, J. (1992) Anal. Chem. 64, 779-785.
37. Shibuki, K. (1990) Neurosci. Res. 9, 69-76.
38. Malinski, T., and Taha, Z. (1992) Nature 358, 676-678.
39. Malinski, T., Radomski, M. W., Taha, Z., and Moncada, S. (1993) Biochem. Biophys. Res. Commun. 194, 960-965.
40. Wink, D. A., Darbyshire, J. F., Nims, R. W., Saavedra, J. E., and Ford, P. C. (1993) Chem. Res. Toxicol. 6, 23-29.
41. Keim, M., Feelisch, M., Grube, R., Motz, W., and Strauer, B. E. (1992) in The Biology of Nitric Oxide (Moncada, S., Marietta, M. A., Hibbs, J. B., and Higgs, E. A., Eds.), Portland Press, Portland, OR.
42. Leone, A. M., Francis, P. L., Rhodes, P., and Moncada, S. (1994) Biochem. Biophys. Res. Commun. 200, 951-957.
43. Rhodes, P., Leone, A. M., Francis, P. L., Struthers, A. D., and Moncada, S. (1995) Biochem. Biophys. Res. Commun. 209, 590-596.
44. Tannenbaum, S. R., Sinskey, A. J., Weisman, M., and Bishop, W. (1974) J. Natl. Cancer Inst. 53, 79-84.
45. Bos, P. M. J., Van Den Brendt, P. A., Wedel, M., and Ockhuizen, T. (1988) Food Chem. Toxicol. 26, 93-97.
46. Benjamin, N., O'Driscoll, F., Dougall, H., Duncan, C., Smith, L., Golden, M., and McKenzie, H. (1994) Nature 368, 502.
47. Tomoda, A., Yubisui, T., Tsuji, A., and Yoneyama, Y. (1979) J. Biol. Chem. 254, 3119-3123.
48. Tesch, J. W., Rehg, W. R., and Sievers, R. E. (1976) J. Chromatog. 126, 743-755.
49. Green, L. C., Ruiz de Liuzuriaga, K., Wagner, D. A., Rand, W., Istfan, N., Young, V. R., and Tannenbaum, S. R. (1981) Proc. Natl. Acad. Sci. USA 78, 7764-7768.
50. Marietta, M. A., Yoon, P. S., Iyengar, R., Leaf, C. D., and Wishnok, J. S. (1988) Biochemistry 27, 8706-8711.
51. Follett, M. J., and Ratcliff, P. W. (1963) J. Sci. Food Agric. 14, 138-144.
52. Leone, A. M., personal communication.
53. Stamler, J. S., personal communication.
54. Jia, L., Bonaventura, C., Bonaventura, J., and Stamler, J. S. (1996) Nature 380, 221-226.
55. Lancaster, J. R. (1994) Proc. Natl. Acad. Sci. USA 91, 8137-8141.
56. Vallance, P., Collier, J., and Moncada, S. (1989) Lancet 334, 997-1000.
57. Furchgott, R. F. (1984) Annu. Rev. Pharmacol. Toxicol. 24, 175-197.
58. Moncada, S., Palmer, R. M. J., and Higgs, E. A. (1991) Pharmacol. Rev. 43, 109-142.
59. Rubanyi, G. M., Johns, A., Wilcox, D., Bates, F. N., and Harrison, D. (1991) J. Cardiovasc. Pharmacol. 17, S41-S45.
60. Barnett, D. J., Rios, A., and Williams, D. L. H. (1995) J. Chem. Soc. Perkin Trans. 2, 1279-1282.
61. Leone, A. M., personal communication.
62. Furchgott, R. F., Martin, W., Cherry, P. D., Jothianandan, D., and Villani, G. M. (1985) Vascular Neuroeffector Mechanisms (Bevan, J. A., Godfraind, T., Maxwell, R. A., Stoclet, J. C., and Worcel, M. Eds.), pp. 105-114, Elsevier, Amsterdam.
63. Karlsson, J. O. G., Axelsson, K. K., and Andersson, R. G. G. (1984) Life Sci. 34, 1555-1563.
64. Sexton, D. J., Muruganandam, A., McKenney, D. J., and Mutus, B. (1994) Photochem. Photobiol. 59, 463-467.
65. Megson, I. L., Flitney, F. W., Bates, J., and Webster, R. R. (1995) Endothelium 3, 39-44.
66. Gibson, A., Babbedge, R., Brave, S. R., Hart, S. L., Hobbs, A. J., Tucker, J. F., Wallace, P., and Moore, P. K. (1992) Br. J. Pharmacol. 107, 715-721.
67. Barbier, A. J. M., and Lefebvre, R. A. (1992) Eur. J. Pharmacol. 219, 331-334.
68. Liu, X., Gillespie, J. S., and Martin, W. (1994) Br. J. Pharmacol. 111, 1287-1295.
69. Jansen, A., Drazen, J., Osborne, J. A., Brown, R., Loscalzo, J., and Stamler, J. S. (1992) J. Pharmacol. Exp. Ther. 261, 154-160.
70. Wood, J., and Garthwaite, J. (1994) Neuropharmacology 33, 1235-1244.
71. Maraj, S. R., Khan, S., Cui, X-Y., Cammack, R., Joannou, C. L., and Hughes, M. N. (1995) Analyst 120, 699-709.
72. Hughes, M. N., and Khan, S., unpublished observation.
73. Ioannidis, I., Bätz, M., Paul, T., Korth, H-G., Sustmann, R., and de Groot, H. (1996) Biochem. J., in press.
74. Swift, H. R., and Williams, D. L. H., unpublished observations.
75. Butler, A. R., and Renton, L., unpublished observations.
76. Kharitonov, V. G., Sundquist, A. R., and Sharma, V. S. (1995) J. Biol. Chem. 270, 28158-28164.
77. Goldstein, S., and Czapski, G. (1996) J. Am. Chem. Soc. 118, 349-3425.
78. Stamler, J. S., Simon, D. I., Osborne, J. A., Mullins, M. E., Jaraki, O., Michel, T., Singel, D. J., and Loscalzo, J. (1992) Proc. Natl. Acad. Sci. USA 89, 444-448.
79. Hausladen, A., Privalle, C. T., Keng, T., DeAngelo, J., and Stamler, J. S. (1996) Cell 86, 719-729.
80. De Groote, M. A., Granger, D., Xu, Y., Campbell, G., Prince, R., and Fang, F. C. (1995) Proc. Natl. Acad. Sci. USA 92, 6399-6403.
81. De Groote, M. A., Testerman, T., Xu, Y., Stauffer, G., and Fang, F. C. (1996) Science 272, 414-416.
82. Pepke-Zaba, J., Higenbottam, T. W., Dinh-Xuan, A. T., Stone, D., and Wallwork, J. (1991) Lancet 338, 1173-1174.
83. Gerzer, R., Karrenbrock, W., Seiss, W., and Heim, J. H. (1988) Thromb. Res. 52, 11-21.
84. Radomski, M. W., Rees, D. D., Dutra, A., and Moncada, S. (1992) Br. J. Pharmacol. 107, 745-749.
85. Askew, S. C., Butler, A. R., Flitney, F. W., Kemp, G. D., and Megson, I. L. (1995) Bioorg. Med. Chem. 3, 1-9.
86. Lieberman, E. H., O'Neill, S., and Mendelsohn, M. (1991) Circ. Res. 68, 1722-1728.
87. Mendelsohn, M. E., O'Neill, S., George, D., and Loscalzo, J. (1990) J. Biol. Chem. 265, 19028-19034.
88. Langford, E. J., Brown, A. S., Wainwright, R. J., de Belder, A. J., Thomas, M. R., Smith, R. E. A., Radomski, M. W., Martin, J. F., and Moncada, S. (1994) Lancet 344, 1458-1460.
89. de Belder, A., Lees, C., Martin, J., Moncada, S., and Campbell, S. (1995) Lancet 345, 124-125.