A novel class of nitrovasodilators: Potency and in vitro tolerance of organic aminoalkylnitrates

Journal of Cardiovascular Pharmacology

Volumn 56, Issue 5, 2010, Pages 484-490

  Roegler, Carolin ^a   König, Andreas ^a   Glusa, Erika ^a   Lehmann, Jochen ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

nitrate tolerance; organic nitrates; structure activity relationships; vasorelaxation

Indexed keywords

AMINO ACID; GLYCERYL TRINITRATE; ORGANIC NITRATE; PROSTAGLANDIN F2 ALPHA; VASODILATOR AGENT;

ANIMAL TISSUE; ARTERY ENDOTHELIUM; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG TOLERANCE; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; PULMONARY ARTERY; STRUCTURE ACTIVITY RELATION; SWINE; TACHYPHYLAXIS; VASODILATATION;

ANIMALS; DINOPROST; DOSE-RESPONSE RELATIONSHIP, DRUG; NITRATES; NITROGLYCERIN; PULMONARY ARTERY; QUATERNARY AMMONIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE; TACHYPHYLAXIS; VASODILATION; VASODILATOR AGENTS;

EID: 78649371121     PISSN: 01602446     EISSN: None     Source Type: Journal    
DOI: 10.1097/FJC.0b013e3181f231da     Document Type: Article

References (19)

1. Murad F. Cellular signaling with nitric oxide and cyclic GMP. Braz J Med Biol Res. 1999;32:1317-1327.
2. Daiber A, Wenzel P, Oelze M, et al. New insights into bioactivation of organic nitrates, nitrate tolerance and cross-tolerance. Clin Res Cardiol. 2008;97:12-20.
3. Chen Z, Zhang J, Stamler JS. Identification of the enzymatic mechanism of nitroglycerin bioactivation. Proc Natl Acad Sci USA. 2002;99:8306-8311.
4. Wenzel P, Hink U, Oelze M, et al. Number of nitrate groups determines reactivity and potency of organic nitrates: a proof of concept study in ALDH-2-/-mice. Br J Pharmacol. 2007;150:526-533.
5. Munzel T, Daiber A, Mulsch A. Explaining the phenomenon of nitrate tolerance. Circ Res. 2005;97:618-628.
6. Needleman P, Jakschik B, Johnson EM Jr. Sulfhydryl requirement for relaxation of vascular smooth muscle. J Pharmacol Exp Ther. 1973;187: 324-331.
7. Munzel T, Sayegh H, Freeman BA, et al. Evidence for enhanced vascular superoxide anion production in nitrate tolerance. A novel mechanism underlying tolerance and cross-tolerance. J Clin Invest. 1995; 95:187-194.
8. Kojda G, Hacker A, Noack E. Effects of nonintermittent treatment of rabbits with pentaerythritol tetranitrate on vascular reactivity and superoxide production. Eur J Pharmacol. 1998;355:23-31.
9. Daiber A, Oelze M, Coldewey M, et al. Oxidative stress and mitochondrial aldehyde dehydrogenase activity: a comparison of pentaerythritol tetranitrate with other organic nitrates. Mol Pharmacol. 2004;66:1372-1382.
10. Wenzel P, Oelze M, Coldewey M, et al. Heme oxygenase-1: a novel key player in the development of tolerance in response to organic nitrates. Arterioscler Thromb Vasc Biol. 2007;27:1729-1735.
11. Koenig A, Roegler C, Lange K, et al. NO donors. Part 16: investigations on structure-activity relationships of organic mononitrates reveal 2-nitrooxyethylammoniumnitrate as a high potent vasodilator. Bioorg Med Chem Lett. 2007;17:5881-5885.
12. Schuhmacher S, Schulz E, Oelze M, et al. A new class of organic nitrates: investigations on bioactivation, tolerance and cross-tolerance phenomena. Br J Pharmacol. 2009;158:510-520.
13. Koenig A, Lange K, Konter J, et al. Potency and in vitro tolerance of organic nitrates: partially denitrated metabolites contribute to the tolerance-devoid activity of pentaerythrityl tetranitrate. J Cardiovasc Pharmacol. 2007;50:68-74.
14. Barbière J. Estérification nitrique et nitration d'amino-alcools. Bull Soc Chim Fr. 1944;11:470-480.
15. Ishihara S, Saito F, Ohhata Y, et al. Synthesis and collateral dilator activity of nitroxyalkylamides having direct or latent sulfhydryl moieties. Bioorg Med Chem Lett. 2003;13:1527-1530.
16. Ranatunge RR, Augustyniak ME, Dhawan V, et al. Synthesis and anti-inflammatory activity of a series of N-substituted naproxen glycolamides: nitric oxide-donor naproxen prodrugs. Bioorg Med Chem. 2006;14:2589-2599.
17. Romanova LB, Ivanovo ME, Nesterenko DA, et al. Synthesis of nitroxyalkylammonium nitrates. Russ Chem Bull. 1994;43:1207-1208.
18. Glusa E, Adam C. Endothelium-dependent relaxation induced by cathepsin G in porcine pulmonary arteries. Br J Pharmacol. 2001;133:422-428.
19. Lange K, Koenig A, Roegler C, et al. NO donors. Part 18: Bioactive metabolites of GTN and PETN-synthesis and vasorelaxant properties. Bioorg Med Chem Lett. 2009;19:3141-3144.