Characterization of the antioxidant properties of pentaerithrityl tetranitrate (PETN)-induction of the intrinsic antioxidative system heme oxygenase-1 (HO-1)

Methods in Molecular Biology

Volumn 594, Issue , 2010, Pages 311-326

  Daiber, Andreas ^a   Münzel, Thomas ^a  

^a NONE

Author keywords

Endothelial dysfunction; Heme oxygenase 1 (HO 1); Mitochondrial aldehyde dehydrogenase (ALDH 2); Nitrate tolerance; Reactive oxygen species; Vascular oxidative stress

Indexed keywords

ANTIOXIDANT; HEME OXYGENASE 1; PENTAERYTHRITYL TETRANITRATE;

ANIMAL; ARTICLE; DRUG EFFECT; ENZYME INDUCTION; GENETICS; MALE; METABOLISM; RAT; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; WISTAR RAT;

ANIMALS; ANTIOXIDANTS; ENZYME INDUCTION; HEME OXYGENASE-1; MALE; PENTAERYTHRITOL TETRANITRATE; RATS; RATS, WISTAR; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION;

EID: 77950350705     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-60761-411-1_22     Document Type: Article

References (35)

1. Munzel T, Daiber A, Mulsch A (2005) Explaining the phenomenon of nitrate tolerance. Circ Res 97:618-28
2. Munzel T, Sayegh H, Freeman BA, Tarpey MM, Harrison DG (1995) Evidence for enhanced vascular superoxide anion production in nitrate tolerance. A novel mechanism underlying tolerance and cross-tolerance. J Clin Invest 95:187-94
3. Schulz E, Tsilimingas N, Rinze R, Reiter B, Wendt M, Oelze M, Woelken-Weckmuller S, Walter U, Reichenspurner H, Meinertz T, Munzel T (2002) Functional and biochemical analysis of endothelial (dys)function and NO/cGMP signaling in human blood vessels with and without nitroglycerin pretreatment. Circulation 105:1170-5
4. Daiber A, Oelze M, Sulyok S, Coldewey M, Schulz E, Treiber N, Hink U, Mulsch A, Scharffetter-Kochanek K, Munzel T (2005) Heterozygous defciency of manganese super-oxide dismutase in mice (Mn-SOD+/-): a novel approach to assess the role of oxidative stress for the development of nitrate tolerance. Mol Pharmacol 68:579-88
5. Hink U, Oelze M, Kolb P, Bachschmid M, Zou MH, Daiber A, Mollnau H, August M, Baldus S, Tsilimingas N, Walter U, Ullrich V, Munzel T (2003) Role for peroxynitrite in the inhibition of prostacyclin synthase in nitrate tolerance. J Am Coll Cardiol 42:1826-34
6. Daiber A, Oelze M, Coldewey M, Bachschmid M, Wenzel P, Sydow K, Wendt M, Kleschyov AL, Stalleicken D, Ullrich V, Mulsch A, Munzel T (2004) Oxidative stress and mito-chondrial aldehyde dehydrogenase activity: a comparison of pentaerythritol tetranitrate with other organic nitrates. Mol Pharmacol 66:1372-82
7. Kojda G, Hacker A, Noack E (1998) Effects of nonintermittent treatment of rabbits with pen-taerythritol tetranitrate on vascular reactivity and superoxide production. Eur J Pharmacol 355:23-31
8. Hacker A, Muller S, Meyer W, Kojda G (2001) The nitric oxide donor pentaerythritol tet-ranitrate can preserve endothelial function in established atherosclerosis. Br J Pharmacol 132:1707-14
9. Fink B, Bassenge E (1997) Unexpected, tolerance-devoid vasomotor and platelet actions of pentaerythrityl tetranitrate. J Cardiovasc Pharmacol 30:831-6
10. Dikalov S, Fink B, Skatchkov M, Stalleicken D, Bassenge E (1998) Formation of reactive oxygen species by pentaerithrityltetranitrate and glyceryl trinitrate in vitro and development of nitrate tolerance. J Pharmacol Exp Ther 286:938-44
11. Abou-Mohamed G, Johnson JA, Jin L, El-Remessy AB, Do K, Kaesemeyer WH, Caldwell RB, Caldwell RW (2004) Roles of superoxide, peroxynitrite, and protein kinase C in the development of tolerance to nitro-glycerin. J Pharmacol Exp Ther 308:289-99
12. Kuzkaya N, Weissmann N, Harrison DG, Dikalov S (2003) Interactions of peroxyni-trite, tetrahydrobiopterin, ascorbic acid, and thiols: implications for uncoupling endothe-lial nitric-oxide synthase. J Biol Chem 278:22546-54
13. Wang EQ, Lee WI, Fung HL (2002) Lack of critical involvement of endothelial nitric oxide synthase in vascular nitrate tolerance in mice. Br J Pharmacol 135:299-302
14. Abou-Mohamed G, Kaesemeyer WH, Caldwell RB, Caldwell RW (2000) Role of l-arginine in the vascular actions and development of tolerance to nitroglycerin. Br J Pharmacol 130:211-8
15. Thomas GR, DiFabio JM, Tommaso T, Parker JD (2007) Once daily therapy with isosorbide-5-mononitrate causes endothelial dysfunction in humans: evidence of a free radical mediated mechanism. J Am Coll Cardiol 49:1289-1295
16. Sekiya M, Sato M, Funada J, Ohtani T, Akutsu H, Watanabe K (2005) Effects of the long-term administration of nicorandil on vascular endothelial function and the progression of arteriosclerosis. J Cardiovasc Pharmacol 46: 63-7
17. Munzel T, Kurz S, Rajagopalan S, Thoenes M, Berrington WR, Thompson JA, Freeman BA, Harrison DG (1996) Hydralazine prevents nitroglycerin tolerance by inhibiting activation of a membrane-bound NADH oxi-dase. A new action for an old drug. J Clin Invest 98:1465-70
18. Banerjee S, Tang XL, Qiu Y, Takano H, Manchikalapudi S, Dawn B, Shirk G, Bolli R (1999) Nitroglycerin induces late preconditioning against myocardial stunning via a PKC-dependent pathway. Am J Physiol 277: H2488-94
19. Otto A, Fontaine D, Fontaine J, Berkenboom G (2005) Rosuvastatin treatment protects against nitrate-induced oxidative stress. J Cardiovasc Pharmacol 46:177-84
20. Salvemini D, Pistelli A, Mollace V (1993) Release of nitric oxide from glyceryl trinitrate by captopril but not enalaprilat: in vitro and in vivo studies. Br J Pharmacol 109:430-6
21. Schwemmer M, Bassenge E (2003) New approaches to overcome tolerance to nitrates. Cardiovasc Drugs Ther 17:159-73
22. Gori T, Al-Hesayen A, Jolliffe C, Parker JD (2003) Comparison of the effects of pen-taerythritol tetranitrate and nitroglycerin on endothelium-dependent vasorelaxation in male volunteers. Am J Cardiol 91:1392-4
23. Jurt U, Gori T, Ravandi A, Babaei S, Zeman P, Parker JD (2001) Differential effects of pentaerythritol tetranitrate and nitroglycerin on the development of tolerance and evidence of lipid peroxidation: a human in vivo study. J Am Coll Cardiol 38:854-9
24. Oberle S, Abate A, Grosser N, Hemmerle A, Vreman HJ, Dennery PA, Schneider HT, Stalleicken D, Schroder H (2003) Endothelial protection by pentaerithrityl trinitrate: bili-rubin and carbon monoxide as possible mediators. Exp Biol Med (Maywood) 228:529-34
25. Oberle S, Schwartz P, Abate A, Schroder H (1999) The antioxidant defense protein ferri-tin is a novel and specifc target for pentaer-ithrityl tetranitrate in endothelial cells. Biochem Biophys Res Commun 261:28-34
26. Grosser N, Schroder H (2004) Therapy with NO donors-antiatherogenic and antioxidant actions. Herz 29:116-22
27. Koenig A, Lange K, Konter J, Daiber A, Stalleicken D, Glusa E, Lehmann J (2007) Potency and in vitro tolerance of organic nitrates: partially denitrated metabolites contribute to the tolerance-devoid activity of pen-taerythrityl tetranitrate. J Cardiovasc Pharmacol 50:68-74
28. Wenzel P, Oelze M, Coldewey M, Hortmann M, Seeling A, Hink U, Mollnau H, Stalleicken D, Weiner H, Lehmann J, Li H, Forstermann U, Munzel T, Daiber A (2007) Heme oxygenase-1: a novel key player in the development of tolerance in response to organic nitrates. Arterioscler Thromb Vasc Biol 27:1729-35
29. Minetti M, Mallozzi C, Di Stasi AM, Pietraforte D (1998) Bilirubin is an effective antioxidant of peroxynitrite-mediated protein oxidation in human blood plasma. Arch Biochem Biophys 352:165-74
30. Mollnau H, Wenzel P, Oelze M, Treiber N, Pautz A, Schulz E, Schuhmacher S, Reifenberg K, Stalleicken D, Scharffetter-Kochanek K, Kleinert H, Munzel T, Daiber A (2006) Mitochondrial oxidative stress and nitrate tolerance-comparison of nitroglyc-erin and pentaerithrityl tetranitrate in Mn-SOD+/-mice. BMC Cardiovasc Disord 6:44
31. Sydow K, Daiber A, Oelze M, Chen Z, August M, Wendt M, Ullrich V, Mulsch A, Schulz E, Keaney JF Jr, Stamler JS, Munzel T (2004) Central role of mitochondrial aldehyde dehy-drogenase and reactive oxygen species in nitroglycerin tolerance and cross-tolerance. J Clin Invest 113:482-9
32. Livak KJ, Schmittgen TD (2001) Analysis of relative gene expression data using real-time quantitative PCR and the 2(-Delta Delta C(T)) Method. Methods 25:402-8
33. Parviainen MT (1997) A modifcation of the acid diazo coupling method (Malloy-Evelyn) for the determination of serum total bilirubin. Scand J Clin Lab Invest 57:275-9
34. Daiber A, Oelze M, August M, Wendt M, Sydow K, Wieboldt H, Kleschyov AL, Munzel T (2004) Detection of superoxide and per-oxynitrite in model systems and mitochondria by the luminol analogue L-012. Free Radic Res 38:259-69
35. Daiber A, Oelze M, Coldewey M, Kaiser K, Huth C, Schildknecht S, Bachschmid M, Nazirisadeh Y, Ullrich V, Mulsch A, Munzel T, Tsilimingas N (2005) Hydralazine is a powerful inhibitor of peroxynitrite formation as a possible explanation for its benefcial effects on prognosis in patients with congestive heart failure. Biochem Biophys Res Commun 338:1865-74