Bioactivation of nitroglycerin by ascorbate

Molecular Pharmacology

Volumn 72, Issue 1, 2007, Pages 191-196

  Kollau, Alexander ^a   Beretta, Matteo ^a   Gorren, Antonius C F ^a   Russwurm, Michael ^b   Koesling, Doris ^b   Schmidt, Kurt ^a   Mayer, Bernd ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ASCORBIC ACID; GLYCEROL 1,2 DINITRATE; GLYCEROL 1,3 DINITRATE; GLYCERYL TRINITRATE; GUANYLATE CYCLASE; HEME; NITRIC OXIDE; OXYHEMOGLOBIN; SUPEROXIDE; SUPEROXIDE DISMUTASE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG ACTIVATION; DRUG DETERMINATION; ENZYME ACTIVATION; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; ASCORBIC ACID; BIOTRANSFORMATION; CELLS, CULTURED; ENZYME ACTIVATION; GUANYLATE CYCLASE; HYDRAZINES; NITROGLYCERIN; RATS;

EID: 34347268076     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.107.035642     Document Type: Article

References (37)

1. Abou-Mohamed G, Johnson JA, Jin L, El-Remessy AB, Do K, Kaesemeyer WH, Caldwell RB, and Caldwell RW (2004) Roles of superoxide, peroxynitrite, and protein kinase C in the development of tolerance to nitroglycerin. J Pharmacol Exp Ther 308:289-299.
2. Archer MC, Tannenbaum SR, Fan TY, and Weisman M (1975) Reaction of nitrite with ascorbate and its relation to nitrosamine formation. J Natl Cancer Inst 54:1203-1205.
3. Artz JD, Toader V, Zavorin SI, Bennett BM, and Thatcher GRJ (2001) In vitro activation of soluble guanylyl cyclase and nitric oxide release: a comparison of NO donors and NO mimetics. Biochemistry 40:9256-9264.
4. Bassenge E and Fink B (1996) Tolerance to nitrates and simultaneous upregulation of platelet activity prevented by enhancing antioxidant state. Naunyn Schmiedebergs Arch Pharmacol 353:363-367.
5. Bassenge E, Fink N, Skatchkov M, and Fink B (1998) Dietary supplement with vitamin C prevents nitrate tolerance. J Clin Invest 102:67-71.
6. Bennett BM, Leitman DC, Schroder H, Kawamoto JH, Nakatsu K, and Murad F (1989) Relationship between biotransformation of glyceryl trinitrate and cyclic GMP accumulation in various cultured cell lines. J Pharmacol Exp Ther 250:316-323.
7. Craven PA and DeRubertis FR (1978) Restoration of the responsiveness of purified guanylate cyclase to nitrosoguanidine, nitric oxide, and related activators by heme and hemeproteins. Evidence for involvement of the paramagnetic nitrosyl-heme complex in enzyme activation. J Biol Chem 253:8433-8443.
8. Dikalov S, Fink B, Skatchkov M, and Bassenge E (1999) Comparison of glyceryl trinitrate-induced with pentaerythrityl tetranitrate-induced in vivo formation of superoxide radicals: effect of vitamin C. Free Rad Biol Med 27:170-176.
9. Friebe A, Malkewitz J, Schultz G, and Koesling D (1996) Positive effects of pollution? Nature 382:120.
10. Fung HL (2004) Biochemical mechanism of nitroglycerin action and tolerance: is this old mystery solved? Annu Rev Pharmacol Toxicol 44:67-85.
11. Gorren ACF, Russwurm M, Kollau A, Koesling D, Schmidt K, and Mayer B (2005) Effects of nitroglycerin/L-cysteine on soluble guanylate cyclase: evidence for an activation/inactivation equilibrium controlled by nitric oxide binding and haem oxidation. Biochem J 390:625-631.
12. Gorren ACF, Schrammel A, Schmidt K, and Mayer B (1996) Decomposition of S-nitrosoglutathione in the presence of copper and glutathione. Arch Biochem Biophys 330:219-228.
13. Hinz B and Schröder H (1998) Vitamin C attenuates nitrate tolerance independently of its antioxidant effect. FEBS Lett 428:97-99.
14. Ignarro LJ, Barry BK, Gruetter DJ, Edwards JC, Ohlstein EH, Gruetter CA, and Baricos WH (1980) Guanylate cyclase activation by nitroprusside and nitrosoguanidine is related to formation of S-nitrosothiol intermediates. Biochem Biophys Res Commun 94:93-100.
15. Ignarro LJ and Gruetter CA (1980) Requirement of thiols for activation of coronary arterial guanylate cyclase by glyceryl trinitrate and sodium nitrite: possible involvement of S-nitrosothiols. Biochim Biophys Acta 631:221-231.
16. Kashiba-Iwatsuki M, Yamaguchi M, and Inoue M (1996) Role of ascorbic acid in the metabolism of S-nitroso-glutathione. FEBS Lett 389:149-152.
17. Katsuki S, Arnold WP, Mittal CK, and Murad F (1977) Stimulation of guanylate cyclase by sodium nitroprusside, nitroglycerin and nitric oxide in various tissue preparations and comparison to the effects of sodium azide and hydroxylamine. J Cyclic Nucleotide Res 3:23-35.
18. Kollau A, Hofer A, Russwurm M, Koesling D, Keung WM, Schmidt K, Brunner F, and Mayer B (2005) Contribution of aldehyde dehydrogenase to mitochondrial bioactivation of nitroglycerin. Evidence for activation of purified soluble guanylyl cyclase via direct formation of nitric oxide. Biochem J 385:769-777.
19. Maragos CM, Morley D, Wink DA, Dunams TM, Saavedra JE, Hoffman A, Bove AA, Isaac L, Hrabie JA, and Keefer LK (1991) Complexes of NO with nucleophiles as agents for the controlled biological release of nitric oxide-vasorelaxant effects. J Med Chem 34:3242-3247.
20. May JM (2000) How does ascorbic acid prevent endothelial dysfunction? Free Rad Biol Med 28:1421-1429.
21. Mülsch A, Oelze M, Kloss S, Mollnau H, Topfer A, Smolenski A, Walter U, Stasch JP, Warnholtz A, Hink U, et al. (2001) Effects of in vivo nitroglycerin treatment on activity and expression of the guanylyl cyclase and cGMP-dependent protein kinase and their downstream target vasodilator-stimulated phosphoprotein in aorta. Circulation 103:2188-2194.
22. Murphy ME (1999) Ascorbate and dehydroascorbate modulate nitric oxide-induced vasodilations of rat coronary arteries. J Cardiovasc Pharmacol 34:295-303.
23. Russwurm M and Koesling D (2005) Purification and characterization of no-sensitive guanylyl cyclase. Methods Enzymol 396:492-501.
24. Schmidt K, Desch W, Klatt P, Kukovetz WR, and Mayer B (1997) Release of nitric oxide from donors with known half-life: a mathematical model for calculating nitric oxide concentrations in aerobic solutions. Naunyn Schmiedebergs Arch Pharmacol 355:457-462.
25. Schmidt K, Klatt P, and Mayer B (1994) Reaction of peroxynitrite with oxyhaemoglobin: interference with photometrical determination of nitric oxide. Biochem J 301:645-647.
26. Schrammel A, Koesling D, Schmidt K, and Mayer B (2000) Inhibition of purified soluble guanylyl cyclase by L-ascorbic acid. Cardiovasc Res 47:602-608.
27. Schröder H, Leitman DC, Bennett BM, Waldman SA, and Murad F (1988) Glyceryl trinitrate-induced desensitization of guanylate cyclase in cultured rat lung fibroblasts. J Pharmacol Exp Ther 245:413-418.
28. Schultz G and Böhme E (1984) Guanylate cyclase. GTP pyrophosphate-lyase (cyclizing), E.C. 4.6.1.2, in Methods of Enzymatic Analysis (Bergmeyer HU, Bergmeyer J, Graßl M eds) pp 379-389, Verlag Chemie, Weinheim, Germany.
29. Singel DJ and Stamler JS (2005) Chemical physiology of blood flow regulation by red blood cells: the role of nitric oxide and S- nitrosohemoglobin. Annu Rev Physiol 67:99-145.
30. Singh RJ, Hogg N, Joseph J, and Kalyanaraman B (1996) Mechanism of nitric oxide release from S-nitrosothiols. J Biol Chem 271:18596-18603.
31. Thatcher GRJ and Weldon H (1998) No problem for nitroglycerin: organic nitrate chemistry and therapy. Chem Soc Rev 27:331-337.
32. Turnbull CM, Cena C, Fruttero R, Gasco A, Rossi AG, and Megson IL (2006) Mechanism of action of novel NO-releasing furoxan derivatives of aspirin in human platelets. Br J Pharmacol 148:517-526.
33. Waldman SA, Rapoport RM, Ginsburg R, and Murad F (1986) Desensitization to nitroglycerin in vascular smooth muscle from rat and human. Biochem Pharmacol 35:3525-3531.
34. Wang PG, Xian M, Tang X, Wu X, Wen Z, Cai T, and Janczuk AJ (2002) Nitric oxide donors: chemical activities and biological applications. Chem Rev 102:1091-1134.
35. Watanabe H, Kakihana M, Ohtsuka S, and Sugishita Y (1998a) Randomized, double-blind, placebo-controlled study of ascorbate on the preventive effect of nitrate tolerance in patients with congestive heart failure. Circulation 97:886-891.
36. Watanabe H, Kakihana M, Ohtsuka S, and Sugishita Y (1998b) Randomized, double-blind, placebo-controlled study of the preventive effect of supplemental oral vitamin C on attenuation of development of nitrate tolerance. J Am Coll Cardiol 31:1323-1329.
37. Zhang Y and Hogg N (2005) S-nitrosothiols: cellular formation and transport. Free Rad Biol Med 38:831-838.