Different effects of ascorbate deprivation and classical vascular nitrate tolerance on aldehyde dehydrogenase-catalysed bioactivation of nitroglycerin

British Journal of Pharmacology

Volumn 156, Issue 8, 2009, Pages 1248-1255

  Wenzl, M V ^a   Wolkart G ^a   Stessel, H ^a   Beretta, M ^a   Schmidt, K ^a   Mayer, B ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

Ascorbate level; Bioactivation; Biotransformation; Guinea pig; Mitochondrial aldehyde dehydrogenase; Nitrate tolerance; Nitric oxide; Nitroglycerin; Vascular relaxation; Vitamin C

Indexed keywords

ALDEHYDE DEHYDROGENASE; ALDEHYDE DEHYDROGENASE INHIBITOR; ALDEHYDE DEHYDROGENASE ISOENZYME 2; ASCORBIC ACID; CHLORAL HYDRATE; DAIDZIN; GLYCEROL 1,2 DINITRATE; GLYCEROL 1,3 DINITRATE; GLYCEROL DERIVATIVE; GLYCERYL TRINITRATE; NITRATE; NITROPOHL; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; ASCORBIC ACID DEFICIENCY; BIOTRANSFORMATION; BLOOD VESSEL REACTIVITY; CONTROLLED STUDY; DIETARY INTAKE; DOSE TIME EFFECT RELATION; DRUG ACTIVATION; DRUG TOLERANCE; GUINEA PIG; MUSCLE ISOMETRIC CONTRACTION; NONHUMAN; PRIORITY JOURNAL; TISSUE DISTRIBUTION; VASCULAR RING; VITAMIN BLOOD LEVEL;

ALDEHYDE DEHYDROGENASE; ANIMALS; ASCORBIC ACID; ASCORBIC ACID DEFICIENCY; BIOTRANSFORMATION; CHLORAL HYDRATE; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DOWN-REGULATION; DRUG TOLERANCE; ENZYME ACTIVATION; ENZYME INHIBITORS; FEMALE; GUINEA PIGS; HYDRAZINES; INJECTIONS, SUBCUTANEOUS; ISOFLAVONES; MALE; NITRIC OXIDE; NITRIC OXIDE DONORS; NITROGLYCERIN; TIME FACTORS; VASODILATION; VASODILATOR AGENTS;

EID: 68749098298     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2009.00126.x     Document Type: Article

References (42)

1. Aguirre R, May JM (2008). Inflammation in the vascular bed: importance of vitamin C. Pharmacol Ther 119 : 96 103.
2. Bassenge E, Fink N, Skatchkov M, Fink B (1998). Dietary supplement with vitamin C prevents nitrate tolerance. J Clin Invest 102 : 67 71.
3. Bennett BM, Leitman DC, Schröder H, Kawamoto JH, Nakatsu K, 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.
4. Beretta M, Gruber K, Kollau A, Russwurm M, Koesling D, Goessler W et al. (2008). Bioactivation of nitroglycerin by purified mitochondrial and cyto/ic aldehyde dehydrogenases. J Biol Chem 283 : 17873 17880.
5. Berger J, Shepard D, Morrow F, Taylor A (1989). Relationship between dietary intake and tissue levels of reduced and total vitamin C in the nonscorbutic guinea pig. J Nutr 119 : 734 740.
6. Bonini MG, Stadler K, Sueli de Oliviera S, Corbett J, Dore M, Petranka J et al. (2008). Constitutive nitric oxide synthase activation is a significant route for nitroglycerin-mediated vasodilation. Proc Natl Acad Sci USA 105 : 8569 8574.
7. Brien JF, McLaughlin BE, Bereedon TH, Bennett BM, Nakatsu K, Marks GS (1986). Biotransformation of glyceryl trinitrate occurs concurrently with relaxation of rabbit aorta. J Pharmacol Exp Ther 237 : 608 614.
8. Chen Z, Stamler JS (2006). Bioactivation of nitroglycerin by the mitochondrial aldehyde dehydrogenase. Trends Cardiovasc Medical 16 : 259 265.
9. Chen Z, Zhang J, Stamler JS (2002). Identification of the enzymatic mechanism of nitroglycerin bioactivation. Proc Natl Acad Sci USA 99 : 8306 8311.
10. Chen Z, Foster MW, Zhang J, Mao L, Rockman HA, Kawamoto T et al. (2005). An essential role for mitochondrial aldehyde dehydrogenase in nitroglycerin bioactivation. Proc Natl Acad Sci USA 102 : 12159 12164.
11. Daiber A, Gori T (2008). Vascular tolerance to nitroglycerin in ascorbate deficiency - results are in favor of an important role of oxidative stress in nitrate tolerance. Cardiovasc Res 79 : 722 723.
12. Daiber A, Oelze M, Sulyok S, Coldewey M, Schulz E, Treiber N et al. (2005). Heterozygous deficiency of manganese superoxide dismutase in mice (Mn-SOD+/-): a novel approach to assess the role of oxidative stress for the development of nitrate tolerance. Mol Pharmacol 68 : 579 588.
13. Dalloz F, Maingon P, Cottin Y, Briot F, Horiot JC, Rochette L (1999). Effects of combined irradiation and doxorubicin treatment on cardiac function and antioxidant defenses in the rat. Free Radic Biol Med 26 : 785 800.
14. De La Lande IS, Stepien JM, Philpott AC, Hughes PA, Stafford I, Horowitz JD (2004). Aldehyde dehydrogenase, nitric oxide synthase and superoxide in ex vivo nitrate tolerance in rat aorta. Eur J Pharmacol 496 : 141 149.
15. DiFabio J, Yanbin J, Vasiliou V, Thatcher RJ, Bennett BM (2003). Role of mitochondrial aldehyde dehydrogenase in nitrate tolerance. Mol Pharmacol 64 : 1109 1116.
16. Esplugues JV, Rocha M, Nuñez C, Bosca I, Ibiza S, Herance JR et al. (2006). Complex I dysfunction and tolerance to nitroglycerin: an approach based on mitochondrial-targeted antioxidants. Circ Res 99 : 1067 1075.
17. Hink U, Daiber A, Kayhan N, Trischler J, Kraatz C, Oelze M et al. (2007). Oxidative inhibition of the mitochondrial aldehyde dehydrogenase promotes nitroglycerin tolerance in human blood vessels. J Am Coll Cardiol 50 : 2226 2232.
18. Hinz B, Schröder H (1998). Vitamin C attenuates nitrate tolerance independently of its antioxidant effect. FEBS Lett 428 : 97 99.
19. Huellner MW, Schrepfer S, Weyand M, Weiner H, Wimplinger I, Eschenhagen T et al. (2008). Inhibition of aldehyde dehydrogenase type 2 attenuates vasodilatory action of nitroglycerin in human veins. FASEB J 22 : 2561 2568.
20. Karlsen A, Blomhoff R, Gundersen TE (2007). Stability of whole blood and plasma ascorbic acid. Eur J Clin Nutr 61 : 1233 1236.
21. Kleschyov AL, Oelze M, Daiber A, Huang Y, Mollnau H, Schulz E et al. (2003). Does nitric oxide mediate the vasodilator activity of nitroglycerin? Circulation 93 : 104 112.
22. Kollau A, Hofer A, Russwurm M, Koesling D, Keung WM, Schmidt K et al. (2005). Contribution of aldehyde dehydrogenase to mitochondrial bioactivation of nitroglycerin: evidence for the activation of purified /uble guanylate cyclase through direct formation of nitric oxide. Biochem J 385 : 769 777.
23. Mackenzie IS, Maki-Petaja KM, McEniery CM, Bao YP, Wallace SM, Cheriyan J et al. (2005). Aldehyde dehydrogenase 2 plays a role in the bioactivation of nitroglycerin in humans. Arterioscler Thromb Vasc Biol 25 : 1891 1895.
24. Maeda N, Hagihara H, Nakata Y, Hiller S, Wilder J, Reddick R (2000). Aortic wall damage in mice unable to synthesize ascorbic acid. Proc Natl Acad Sci USA 97 : 841 846.
25. Mahmoodian F, Peterkofsky B (1999). Vitamin C deficiency in guinea pigs differentially affects the expression of type IV collagen, laminin, and elastin in blood vessels. J Nutr 129 : 83 91.
26. Mayer B (2008). Vascular tolerance to nitroglycerin in ascorbate deficiency: results are in favour of an important role of oxidative stress in nitrate tolerance: reply. Cardiovasc Res 79 : 724.
27. Mayer B, Beretta M (2008). The enigma of nitroglycerin bioactivation and nitrate tolerance: news, views, and troubles. Br J Pharmacol 155 : 170 184.
28. Miller MR, Grant S, Wadsworth RM (2008). Selective arterial dilatation by glyceryl trinitrate is not associated with nitric oxide formation in vitro. J Vasc Res 45 : 375 385.
29. Münzel T, Daiber A, Mülsch A (2005). Explaining the phenomenon of nitrate tolerance. Circ Res 97 : 618 628.
30. Núñez C, Víctor VM, Tur R, Alvarez-Barrientos A, Moncada S, Esplugues JV et al. (2005). Discrepancies between nitroglycerin and NO-releasing drugs on mitochondrial oxygen consumption, vasoactivity, and the release of. Circ Res 97 : 1063 1069.
31. Parsons KK, Maeda N, Yamauchi M, Banes AJ, Koller BH (2006). Ascorbic acid-independent synthesis of collagen in mice. Am J Physiol 290 : E1131 E1139.
32. Sage PR, De la Lande IS, Stafford I, Bennett CL, Phillipov G, Stubberfield J et al. (2000). Nitroglycerin tolerance in human vessels: evidence for impaired nitroglycerin bioconversion. Circulation 102 : 2810 2815.
33. Sydow K, Daiber A, Oelze M, Chen ZP, August M, Wendt M et al. (2004). Central role of mitochondrial aldehyde dehydrogenase and reactive oxygen species in nitroglycerin tolerance. J Clin Invest 113 : 482 489.
34. Szöcs K, Lassegue B, Wenzel P, Wendt M, Daiber A, Oelze M et al. (2007). Increased superoxide production in nitrate tolerance is associated with NAD (P) H oxidase and aldehyde dehydrogenase 2 downregulation. J Mol Cell Cardiol 42 : 1111 1118.
35. Tokumaru S, Takeshita S, Nakata R, Tsukamoto I, Kojo S (1996). Change in the level of vitamin C and lipid peroxidation in tissues of the inherently scorbutic rat during ascorbate deficiency. J Agric Food Chem 44 : 2748 2753.
36. Tsukaguchi H, Tokui T, Mackenzle B, Berger UV, Chen XZ, Wang Y et al. (1999). A family of mammalian Na+-dependent L-ascorbic acid transporters. Nature 399 : 70 75.
37. Watanabe H, Kakihana M, Ohtsuka S, 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. (Pubitemid 28113927)
38. Watanabe H, Kakihana M, Ohtsuka S, 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. (Pubitemid 28219123)
39. Wenzel P, Hink U, Oelze M, Schuppan S, Schaeuble K, Schildknecht S et al. (2007a). Role of reduced lipoic acid in the redox regulation of mitochondrial aldehyde dehydrogenase (ALDH-2) activity: implications for mitochondrial oxidative stress and nitrate tolerance. J Biol Chem 282 : 792 799.
40. Wenzel P, Hink U, Oelze M, Seeling A, Isse T, Bruns K et al. (2007b). Number of nitrate groups determines reactivity and potency of organic nitrates: a proof of concept study in ALDH-2-/- mice. Br J Pharmacol 150 : 526 533.
41. Wilson JX (2005). Regulation of vitamin C transport. Annu Rev Nutr 25 : 105 125.
42. Wölkart G, Wenzl MV, Beretta M, Stessel H, Schmidt K, Mayer B (2008). Vascular tolerance to nitroglycerin in ascorbate deficiency. Cardiovasc Res 79 : 304 312.