Lipophilic S-nitrosothiols: A means of targeted delivery of nitric oxide to areas of endothelial injury?

Drugs of the Future

Volumn 27, Issue 8, 2002, Pages 777-784

  Megson, Ian L ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID 3 (NITROXYMETHYL)PHENYL ESTER; ANTITHROMBOCYTIC AGENT; COPPER ZINC SUPEROXIDE DISMUTASE; CYCLIC GMP; GUANYLATE CYCLASE; N (S NITROSO N ACETYLPENICILLAMINE) 2 AMINO 2 DEOXY 1,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSE; N ACETYL S NITROSOPENICILLAMINE; NITRIC OXIDE; NITRIC OXIDE DONOR; PROTEIN DISULFIDE ISOMERASE; RIG 200; S NITROSO N HEPTANOYLPENICILLAMINE; S NITROSO N PROPIONYLPENICILLAMINE; S NITROSO N VALERYLPENICILLAMINE; S NITROSOTHIOL; UNCLASSIFIED DRUG;

ATHEROSCLEROSIS; BLOOD VESSEL INJURY; CAPACITANCE BLOOD VESSEL; DRUG DELIVERY SYSTEM; DRUG TARGETING; DRUG TOLERANCE; HUMAN; LIPOPHILICITY; NONHUMAN; RESTENOSIS; REVIEW; THROMBOCYTE; THROMBOSIS; TISSUE SPECIFICITY; VASCULAR ENDOTHELIUM; VASCULAR SMOOTH MUSCLE; VASODILATATION;

EID: 0036707318     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2002.027.08.688457     Document Type: Review

References (49)

1. Moncada, S., Palmer, R.M.J., Higgs, E.A. Nitric oxide: Physiology, pathophysiology and pharmacology. Pharmacol Rev 1991, 43: 109-42.
2. Waldman, S., Murad, F. cGMP synthesis and function. Pharmacol Rev 1987, 39: 163-96.
3. Abrams, J. Role of endothelial dysfunction in coronary artery disease. Am J Cardiol 1997, 79: 2-9.
4. Bult, H., Herman, A.G., Matthys, K.E. Antiatherosclerotic activity of drugs in relation to nitric oxide function. Eur J Pharmacol 1999, 375: 157-76.
5. Bennett, B.M., McDonald, B.J., Nigam, R., Simon, W.C. Biotransformation of organic nitrates and vascular smooth muscle cell function. Trends Pharmacol Sci 1994, 15: 245-9.
6. Abrams, J. Pharmacology of nitroglycerin and long-acting nitrates. Am J Cardiol 1985, 56: 12A-18A.
7. Megson, I.L., Webb, D.J. Nitrate resistance in platelets from patients with stable angina pectoris. Circulation 2000, 102: e87.
8. Megson, I.L., Webb, D.J. Nitric oxide donor drugs: Current status and future trends. Exp Opin Invest Drugs 2002, 11: 587-601.
9. De Belder, A.J., MacAllister, R., Radomski, M.W., Moncada, S., Vallance, P. Effects of S-nitroso-glutathione in the human forearm circulation: Evidence for selective inhibition of platelet activation. Cardiovasc Res 1994, 28: 691-4.
10. Scharfstein, J.S., Keaney, J.F., Slivka, A. et al. In vivo transfer of nitric oxide between a plasma protein-bound reservoir and low molecular weight thiols. J Clin Invest 1994, 94: 1432-9.
11. Stamler, J.S., Jaraki, O., Osborne, J. et al. Nitric oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum albumin. Proc Natl Acad Sci USA 1992, 89: 7674-7.
12. Stamler, J.S., Simon, D.I., Osborne, J. et al. S-Nitrosylation of proteins with nitric oxide: Synthesis and characterization of biologically active compounds. Proc Natl Acad Sci USA 1992, 89: 444-8.
13. Gow, A.J., Stamler, J.S. Reactions between nitric oxide and haemoglobin under physiological conditions. Nature 1998, 391: 169-73.
14. Jia, L., Bonaventura, C., Bonaventura, J., Stamler, J.S. S-Nitrosohaemoglobin: A dynamic activity of blood involved in vascular control. Nature 1996, 380: 221-6.
15. 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, 351-3.
16. Williams, D.L.H. S-Nitrosation and the reactions of S-nitroso compounds. Chem Soc Rev 1985, 14: 171-96.
17. Dicks, A.P., Swift, H.R., Williams, D.L.H., Butler, A.R., AlSa'doni, H.H., Cox, B.G. Identification of Cu as the effective reagent in nitric oxide formation from S-nitrosothiols (RSNO). J Chem Soc Perkin Trans 2 1996, 481-7.
18. Jourd'heuil, D., Laroux, F.S., Kang, D., Miles, A.M., Wink, D.A., Grisham, M.B. Stability of S-nitrosothiols in presence of copper, zinc-superoxide dismutase. Meth Enzymol 1999, 301: 220-7.
19. Jourd'heuil, D., Laroux, F.S., Miles, A.M., Wink, D.A., Grisham, M.B. Effect of superoxide dismutase on the stability of S-nitrosothiols. Arch Biochem Biophys 1999, 361: 323-30.
20. Holmes, A.J., Williams, D.L. Reaction of S-nitrosothiols with ascorbate: clear evidence of two reactions. Chem Commun 1998, 1711-2.
21. Jourd'heuil, D., Mai, C.T., Laroux, F.S., Wink, D.A., Grisham, M.B. The reaction of S-nitrosoglutathione with superoxide. Biochem Biophy Res Commun 1998, 246: 525-30.
22. Askew, S.C., Butler, A.R., Flitney, F.W., Kemp, G.D., Megson, I.L. Chemical mechanism underlying the vasodilator and platelet anti-aggregating properties of S-nitroso-N-acetyl-D,L-penicillamine and S-nitrosoglutathione. Bioorg Med Chem 1995, 3: 1-9.
23. Meyer, D.J., Kramer, H., Ozer, N., Coles, B., Ketterer, B. Kinetics and equilibria of S-nitrosothiol-thiol exchange between glutathione, cysteine, penicillamines and serum albumin. FEBS Lett 1994, 345: 177-8.
24. Zai, A., Rudd, A., Scribner, A.W., Loscalzo, J. Cell-surface protein disulfide isomerase catalyzes transnitrosation and regulates intracellular transfer of nitric oxide. J Clin Invest 1999, 103: 393-9.
25. Langford, E.J., Brown, A.S., Wainwright, R.J. et al. Inhibition of platelet activity by S-nitrosoglutathione during coronary angioplasty. Lancet 1994, 344: 1458-60.
26. Molloy, J., Martin, J.F., Baskerville, P.A., Fraser, S.C.A., Markus, H.S. S-nitrosoglutathione reduces the rate of embolization in humans. Circulation. 1998, 98: 1372-5.
27. Kaposzta, Z., Martin, J.F., Markus, H.S. Switching off embolization from symptomatic carotid plaque using S-nitrosoglutathione. Circulation 2002, 105: 1480-4.
28. Maalej, N., Albrecht, R., Loscalzo, J., Folts, J.D. The potent platelet inhibitory effects of S-nitrosated albumin coating of artificial surfaces. J Am Coll Cardiol 1999, 33: 1408-14.
29. Bandarage, U.K., Chen, L., Fang, X. et al. Nitrosothiol esters of diclofenac: Synthesis and pharmacoligical characterization as gastrointestinal-sparing prodrugs. J Med Chem 2000, 43: 4005-16.
30. Del Soldato, P., Sorrentino, R., Pinto, A. NO-aspirins: A class of new antiinflammatory and antithrombotic agents. Trends Pharmacol Sci 1999, 20: 319-23.
31. Momi, S., Emerson, M., Paul, W. et al. Prevention of pulmonary thromboembolism by NCX 4016, a nitric oxide-releasing aspirin. Eur J Pharmacol 2000, 397: 177-85.
32. Fredduzzi, S., Mariucci, G., Tantucci, M., Del Soldato, P., Ambrosini, M.V. Nitro-aspirin (NCX4016) reduces brain damage induced by focal cerebral ischemia in the rat. Neurosci Lett 2001, 302: 121-4.
33. Wainwright, C.L., Miller, A.M., Work, L.M., Del Soldato, P. NCX4016 (NO-aspirin) reduces infarct size and suppresses arrhythmias following myocardial ischaemia/reperfusion in pigs. Br J Pharmacol 2002, 135: 1882-8.
34. Bauer, J.A., Fung, H.L. Differential hemodynamic effects and tolerance properties of nitroglycerin and an S-nitrosothiol in experimental heart failure. J Pharmacol Exp Ther 1991, 256: 249-54.
35. 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 1997, 122: 1617-24.
36. Butler, A.R., Al-Sa'doni, H.H., Megson, I.L., Flitney, F.W. Synthesis, decomposition and vasodilator action of some new S-nitrosated dipeptides. Nitric Oxide 1998, 2: 193-202.
37. Megson, I.L., Morton, S., Greig, I.R. et al. N-Substituted analogues of S-nitroso-N-acetyl-D,L-penicillamine: Chemical stability and prolonged nitric oxide mediated vasodilatation in isolated rat femoral arteries. Br J Pharmacol 1999, 126: 639-48.
38. Sogo, N., Campanella, C., Webb, D.J., Megson, I.L. S-Nitrosothiols cause prolonged, nitric oxide-mediated relaxation in human saphenous vein and internal mammary artery: Therapeutic potential in bypass surgery. Br J Pharmacol 2000, 131: 1236-44.
39. Sogo, N., Wilkinson, I.B., MacCallum, H. et al. A novel S-nitrosothiol (RIG200) causes prolonged relaxation in dorsal hand veins with damaged endothelium. Clin Pharmacol Ther 2000, 68: 75-81.
40. MacAllister, R.J., Calver, A.L., Riezebos, J., Collier, J., Vallance, P. Relative potency of nitrovasodilators on human blood vessels: An insight into the targetting of nitric oxide delivery. J Pharmacol Exp Ther 1995, 273: 1529-37.
41. Weber, A.-A., Neuhaus, T., Seul, C. et al. Biotransformation of glyceryl trinitrate by blood platelets as compared to vascular smooth muscle cells. Eur J Pharmacol 1996, 309: 209-13.
42. Radomski, M.W., Rees, D.D., Dutra, A., Moncada, S. S-Nitroso-glutathione inhibits platelet aggregation in vitro and in vivo. Br J Pharmacol 1992, 107: 745-9.
43. Sogo, N., Magid, K.S., Shaw, C.A., Webb, D.J., Megson, I.L. Inhibition of human platelet aggregation by nitric oxide donor drugs: Relative contribution of cGMP-independent mechanisms. Biochem Biophys Res Commun 2000, 279: 412-9.
44. Wanstall, J.C., Jeffery, T.K., Gambino, A., Lovren, F., Triggle, C.R. Vascular smooth muscle relaxation mediated by nitric oxide donors: A comparison with acetylcholine, nitric oxide and nitroxyl ion. Br J Pharmacol 2001, 134: 463-72.
45. Megson, I.L., Sogo, N., Mazzei, F.A., Butler, A.R., Walton, J.C., Webb, D.J. Inhibition of human platelet aggregation by a novel S-nitrosothiol is abolished by haemoglobin and red blood cells in vitro: Implications for anti-thrombotic therapy. Br J Pharmacol 2000, 131: 1391-8.
46. Miller, M.R., Roseberry, M.J., Mazzei, F.A., Butler, A.R., Webb, D.J., Megson, I.L. S-Nitrosothiols do not induce tolerance and are not cross-tolerant in rat femoral arteries. Eur J Pharmacol 2000, 408: 335-43.
47. 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 1999, 127: 1224-230.
48. Cantuaria, G., Magalhaes, A., Angioli, R. et al. Antitumour activity of a novel glyco-nitric oxide conjugate in ovarian carcinoma. Cancer 2000, 88: 381-8.
49. Khan, F., Greig, I.R., Newton, D.J., Butler, A.R., Belch, J.J.F. Skin blood flow after transdermal S-nitrosothio-acetylglucose. Lancet 1997, 350: 410-1.