Heme-dependent and independent soluble guanylate cyclase activators and vasodilation

Journal of Cardiovascular Pharmacology

Volumn 56, Issue 3, 2010, Pages 229-233

  Priviero, Fernanda B M ^a,b   Webb, R Clinton ^c  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^c MEDICAL COLLEGE OF GEORGIA   (United States)

Author keywords

endothelial dysfunction; nitric oxide; soluble guanylyl cyclase activators; vascular disease; vascular smooth muscle

Indexed keywords

1 BENZYL 3 (5 HYDROXYMETHYL 2 FURYL)INDAZOLE; 2 [1 (2 FLUOROBENZYL) 1H PYRAZOLO[3,4 B]PYRIDIN 3 YL] 5 MORPHOLINO 4,6 PYRIMIDINEDIAMINE; 4 [[4 CARBOXYBUTYL[2 [(4 PHENETHYLBENZYL)OXY]PHENETHYL]AMINO]METHYL]BENZOIC ACID; 4 AMINO 5 CYCLOPROPYL 2 [1 (2 FLUOROBENZYL) 1H PYRAZOLO[3,4 B]PYRIDIN 3 YL]PYRIMIDINE; ANTHRANILIC ACID DERIVATIVE; ATACIGUAT; BAY 63 251; BAY 63 2521; CARBON MONOXIDE; CINACIGUAT; ENZYME; GUANYLATE CYCLASE ACTIVATOR; HEME; HEME DERIVATIVE; HMR 1766; NITRIC OXIDE; NITRIC OXIDE DONOR; RIOCIGUAT; UNCLASSIFIED DRUG;

CARDIOVASCULAR DISEASE; CLINICAL TRIAL; DRUG BINDING; DRUG SYNTHESIS; ENZYME METABOLISM; HEART AFTERLOAD; HEART FAILURE; HEART INFARCTION; HEART INJURY; HEART PRELOAD; HUMAN; NONHUMAN; PRIORITY JOURNAL; PULMONARY HYPERTENSION; REVIEW; THROMBOCYTE AGGREGATION INHIBITION; VASCULAR DISEASE; VASODILATATION;

ANIMALS; ENZYME ACTIVATORS; GUANYLATE CYCLASE; HEME; HUMANS; RECEPTORS, CYTOPLASMIC AND NUCLEAR; VASODILATION;

EID: 77957562992     PISSN: 01602446     EISSN: None     Source Type: Journal    
DOI: 10.1097/FJC.0b013e3181eb4e75     Document Type: Review

References (60)

1. Rees DD, Palmer RM, Hodson H.F., et al A specific inhibitor of nitric oxide formation from L-arginine attenuates endothelium-dependent relaxation. Br J Pharmacol. 1989;96:418-424.
2. Vallance P, Collier J, Moncada S. Effects of endothelium-derived nitric oxide on peripheral arteriolar tone in man. Lancet. 1989;2:997-1000.
3. Chirkov YY, Horowitz JD Impaired tissue responsiveness to organic nitrates and nitric oxide: a new therapeutic frontier? Pharmacol Ther. 2007;116:287-305.
4. Boerrigter G, Costello-Boerrigter LC, Cataliotti A., et al Targeting heme-oxidized soluble guanylate cyclase in experimental heart failure. Hypertension. 2007;49:1128-1133.
5. Lucas KA, Pitari GM, Kazerounian S, et al Guanylyl cyclases and signaling by cyclic GMP. Pharmacol Rev. 2000;52:375-414.
6. Waldman SA, Murad F. Cyclic GMP synthesis and function. Pharmacol Rev. 1987;39:163-196.
7. Maurice DH, Palmer D, Tilley D.G., et al Cyclic nucleotide phosphodi-esterase activity, expression, and targeting in cells of the cardiovascular system. Mol Pharmacol. 2003;64:533-546.
8. Rybalkin SD, Yan C, Bornfeldt K.E., et al Cyclic GMP phosphodiesterases and regulation of smooth muscle function. Circ Res. 2003;93:280-291.
9. Hwang TL, Wu CC, Teng CM Comparison of two soluble guanylyl cyclase inhibitors, methylene blue and ODQ, on sodium nitroprusside-induced relaxation in guinea-pig trachea. Br J Pharmacol. 1998;125: 1158-1163.
10. Ignarro LJ, Wood KS, Wolin MS Activation of purified soluble guanylate cyclase by protoporphyrin IX. Proc Natl Acad Sci U S A. 1982;79: 2870-2873.
11. Gerassimou C, Kotanidou A, Zhou Z., et al Regulation of the expression of soluble guanylyl cyclase by reactive oxygen species. Br J Pharmacol. 2007;150:1084-1091.
12. Morita T, Perrella MA, Lee M.E., et al Smooth muscle cell-derived carbon monoxide is a regulator of vascular cGMP. Proc Natl Acad Sci U S A. 1995;92:1475-1479.
13. Brüne B., Ullrich V. Inhibition of platelet aggregation by carbon monoxide is mediated by activation of guanylate cyclase. Mol Pharmacol. 1987; 32:497-504.
14. Ko FN, Wu CC, Kuo S.C., et al YC-1, a novel activator of platelet guanylate cyclase. Blood. 1994;84:4226-4233.
15. Wu CC, Ko FN, Kuo S.C., et al YC-1 inhibited human platelet aggregation through NO-independent activation of soluble guanylate cyclase. Br J Pharmacol. 1995;116:1973-1978.
16. Stone JR, Marletta MA Synergistic activation of soluble guanylate cyclase by YC-1 and carbon monoxide: implications for the role of cleavage of the iron-histidine bond during activation by nitric oxide. Chem Biol. 1998;5:255-261.
17. Becker EM, Alonso-Alija C, Apeler H., et al NO-independent regulatory site of direct sGC stimulators like YC-1 and BAY 41-2272. BMC Pharmacol. 2001;1:13.
18. Martin E, Lee YC, Murad F. YC-1 activation of human soluble guanylyl cyclase has both heme-dependent and heme-independent components. Proc Natl Acad Sci U S A. 2001;98:12938-12942.
19. Mülsch A., Bauersachs J, Schäfer A, et al Effect of YC-1, an NO-independent, superoxide-sensitive stimulator of soluble guanylyl cyclase, on smooth muscle responsiveness to nitrovasodilators. Br J Pharmacol. 1997;120:681-689.
20. Motterlini R, Sawle P, Hammad J., et al CORM-A1: a new pharmacologically active carbon monoxide-releasing molecule. FASEB J. 2005; 19:284-286.
21. Rothermund L, Friebe A, Paul M., et al Acute blood pressure effects of YC-1-induced activation of soluble guanylyl cyclase in normotensive and hypertensive rats. Br J Pharmacol. 2000;130:205-208.
22. Linder AE, Weber DS, Whitesall S.E., et al Altered vascular reactivity in mice made hypertensive by nitric oxide synthase inhibition. J Cardiovasc Pharmacol. 2005;46:438-444.
23. Straub A, Stasch JP, Alonso-Alija C, et al NO-independent stimulators of soluble guanylate cyclase. Bioorg Med Chem Lett. 2001;11:781-784.
24. Stasch JP, Becker EM, Alonso-Alija C, et al NO-independent regulatory site on soluble guanylate cyclase. Nature. 2001;410:212-215.
25. Stasch JP, Schmidt P, Alonso-Alija C, et al NO- and haem-independent activation of soluble guanylyl cyclase: molecular basis and cardiovascular implications of a new pharmacological principle. Br J Pharmacol. 2002; 136:773-783.
26. Stasch JP, Alonso-Alija C, Apeler H., et al Pharmacological actions of a novel NO-independent guanylyl cyclase stimulator, BAY 41-8543: in vitro studies. Br J Pharmacol. 2002;135:333-343.
27. Sovershaev MA, Egorina EM, Hansen J.B., et al Soluble guanylate cyclase agonists inhibit expression and procoagulant activity of tissue factor. Arterioscler Thromb Vasc Biol. 2009;29:1578-1586.
28. Hobbs AJ, Moncada S. Antiplatelet properties of a novel, non-NO-based soluble guanylate cyclase activator, BAY 41-2272. Vasc Pharmacol. 2003; 40:149-154.
29. Ahluwalia A, Foster P, Scotland R.S., et al Antiinflammatory activity of soluble guanylate cyclase: cGMP-dependent down-regulation of P-selectin expression and leukocyte recruitment. Proc Natl Acad Sci U S A. 2004;101:1386-1391.
30. Thomazzi SM, Moreira J, De Nucci G, et al Inhibitory effects on human eosinophil chemotaxis in vitro by BAY 41-2272, an activator of nitric oxide-independent site of soluble guanylate cyclase. Biochem Pharmacol. 2005;69:875-882.
31. Priviero FB, Baracat JS, Teixeira C.E., et al Mechanisms underlying relaxation of rabbit aorta by BAY 41-2272, a nitric oxide-independent soluble guanylate cyclase activator. Clin Exp Pharmacol Physiol. 2005; 32:728-734.
32. Teixeira CE, Priviero FB, Webb RC Molecular mechanisms underlying rat mesenteric artery vasorelaxation induced by the nitric oxide-independent soluble guanylyl cyclase stimulators BAY 41-2272 [5-cyclopropyl-2-[1-(2-fluorobenzyl)- 1H-pyrazolo[3,4-b]pyridin-3-yl] pyrimidin-4-ylamine] and YC-1 [3-(5'-hydroxymethyl-2'-furyl)-1-benzyl Indazole]. J Pharmacol Exp Ther. 2006;317:258-266.
33. Baracat JS, Teixeira CE, Okuyama C.E., et al Relaxing effects induced by the soluble guanylyl cyclase stimulator BAY 41-2272 in human and rabbit corpus cavernosum. Eur J Pharmacol. 2003;477:163-169.
34. Teixeira CE, Priviero FB, Webb RC Effects of 5-cyclopropyl-2-[1-(2- fluoro-benzyl)-1H-pyrazolo[3,4-b]pyridine-3-yl]pyrimidin-4-ylamine (BAY 41-2272) on smooth muscle tone, soluble guanylyl cyclase activity, and NADPH oxidase activity/expression in corpus cavernosum from wild-type, neuronal, and endothelial nitric-oxide synthase null mice. J Pharmacol Exp Ther. 2007;322:1093-1102.
35. Pyriochou A, Beis D, Koika V., et al Soluble guanylyl cyclase activation promotes angiogenesis. J Pharmacol Exp Ther. 2006;319:663-671.
36. Toque HA, Antunes E, Teixeira C.E., et al Increased cyclic guanosine monophosphate synthesis and calcium entry blockade account for the relaxant activity of the nitric oxide-independent soluble guanylyl cyclase stimulator BAY 41-2272 in the rabbit penile urethra. Urology. 2008;72: 711-715.
37. Teixeira CE, Priviero FB, Claudino M.A., et al Stimulation of soluble guanylyl cyclase by BAY 41-2272 relaxes anococcygeus muscle: interaction with nitric oxide. Eur J Pharmacol. 2006;530:157-165.
38. Mullershausen F, Russwurm M, Friebe A., et al Inhibition of phos-phodiesterase type 5 by the activator of nitric oxide-sensitive guanylyl cyclase BAY 41-2272. Circulation. 2004;109:1711-1713.
39. Teixeira CE, Priviero FB, Todd J Jr, et al Vasorelaxing effect of BAY 41-2272 in rat basilar artery: involvement of cGMP-dependent and independent mechanisms. Hypertension. 2006;47:596-602.
40. Bau FR, Monica FZ, Priviero F.B., et al Evaluation of the relaxant effect of the nitric oxide-independent soluble guanylyl cyclase stimulator BAY 41-2272 in isolated detrusor smooth muscle. Eur J Pharmacol. 2010;637: 171-177.
41. Buys ES, Sips P, Vermeersch P., et al Gender-specific hypertension and responsiveness to nitric oxide in sGCalpha1 knockout mice. Cardiovasc Res. 2008;79:179-186.
42. Evgenov OV, Ichinose F, Evgenov N.V., et al Soluble guanylate cyclase activator reverses acute pulmonary hypertension and augments the pulmonary vasodilator response to inhaled nitric oxide in awake lambs. Circulation. 2004;110:2253-2259.
43. Freitas CF, Morganti RP, Annichino-Bizzacchi JM, et al Effect of BAY 41-2272 in the pulmonary hypertension induced by heparin-protamine complex in anaesthetized dogs. Clin Exp Pharmacol Physiol. 2007; 34:10-14.
44. Dumitrascu R, Weissmann N, Ghofrani H.A., et al Activation of soluble guanylate cyclase reverses experimental pulmonary hypertension and vascular remodeling. Circulation. 2006;113:286-295.
45. Priviero FB, Zemse SM, Teixeira C.E., et al Oxidative stress impairs vasorelaxation induced by the soluble guanylyl cyclase activator BAY 41-2272 in spontaneously hypertensive rats. Am J Hypertens. 2009; 22:493-499.
46. Zanfolin M, Faro R, Araujo E.G., et al Protective effects of BAY 41-2272 (sGC stimulator) on hypertension, heart, and cardiomyocyte hypertrophy induced by chronic L-NAME treatment in rats. J Cardiovasc Pharmacol. 2006;47:391-395.
47. Masuyama H, Tsuruda T, Kato J., et al Soluble guanylate cyclase stimulation on cardiovascular remodeling in angiotensin II-induced hypertensive rats. Hypertension. 2006;48:972-978.
48. Frey R, Mück W, Unger S., et al Single-dose pharmacokinetics, pharma-codynamics, tolerability, and safety of the soluble guanylate cyclase stimulator BAY 63-2521: an ascending-dose study in healthy male volunteers. J Clin Pharmacol. 2008;48:926-934.
49. Schermuly RT, Stasch JP, Pullamsetti S.S., et al Expression and function of soluble guanylate cyclase in pulmonary arterial hypertension. Eur Respir J. 2008;32:881-891.
50. Mittendorf J, Weigand S, Alonso-Alija C, et al Discovery of riociguat (BAY 63-2521): a potent, oral stimulator of soluble guanylate cyclase for the treatment of pulmonary hypertension. Chem Med Chem. 2009;4: 853-865.
51. Lapp H, Mitrovic V, Franz N., et al Cinaciguat (BAY 58-2667) improves cardiopulmonary hemodynamics in patients with acute decompensated heart failure. Circulation. 2009;119:2781-2788.
52. Korkmaz S, Radovits T, Barnucz E., et al Pharmacological activation of soluble guanylate cyclase protects the heart against ischemic injury. Circulation. 2009;120:677-686.
53. Frey R, Mück W, Unger S., et al Pharmacokinetics, pharmacodynamics, tolerability, and safety of the soluble guanylate cyclase activator cinaciguat (BAY 58-2667) in healthy male volunteers. J Clin Pharmacol. 2008;48:1400-1410.
54. Mueck W, Frey R. Population pharmacokinetics and pharmacodynamics of cinaciguat, a soluble guanylate cyclase activator, in patients with acute decompensated heart failure. Clin Pharmacokinet. 2010;49:119-129.
55. Krieg T, Liu Y, Rütz T, et al BAY 58-2667, a nitric oxide-independent guanylyl cyclase activator, pharmacologically post-conditions rabbit and rat hearts. Eur Heart J. 2009;30:1607-1613.
56. Gladwin MT. Deconstructing endothelial dysfunction: soluble guanylyl cyclase oxidation and the NO resistance syndrome. J Clin Invest. 2006; 116:2330-2332.
57. Schindler U, Strobel H, Schönafinger K, et al Biochemistry and pharmacology of novel anthranilic acid derivatives activating heme-oxidized soluble guanylyl cyclase. Mol Pharmacol. 2006;69:1260-1268.
58. Zhou Z, Pyriochou A, Kotanidou A., et al Soluble guanylyl cyclase activation by HMR-1766 (ataciguat) in cells exposed to oxidative stress. Am J Physiol. 2008;295:H1763-H1771.
59. Weissmann N, Hackemack S, Dahal B.K., et al The soluble guanylate cyclase activator HMR1766 reverses hypoxia-induced experimental pulmonary hypertension in mice. Am J Physiol. 2009;297:L658-L665
60. Hoffmann LS, Schmidt PM, Keim Y, et al Distinct molecular requirements for activation or stabilization of soluble guanylyl cyclase upon haem oxidation-induced degradation. Br J Pharmacol. 2009;157: 781-795.