The vasorelaxant effects of 1-nitro-2-phenylethane involve stimulation of the soluble guanylate cyclase-cGMP pathway

Biochemical Pharmacology

Volumn 85, Issue 6, 2013, Pages 780-788

  Brito, Teresinha S ^a   Lima, Francisco J B ^a   Aragão, Karoline S ^a   De Siqueira, Rodrigo J B ^a   Sousa, Pergentino J C ^b   Maia, José G S ^b   Filho, Jairo D ^a   Lahlou, Saad ^a   Magalhães, Pedro J C ^a  

^a FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^b FEDERAL UNIVERSITY OF PARÁ   (Brazil)

Author keywords

Guanylate cyclase stimulation; Nitroderivative

Indexed keywords

1 NITRO 2 PHENYLETHANE; 1H 1,2,4 OXADIAZOLO[4,3 A]QUINOXALIN 1 ONE; 4 AMINOPYRIDINE; ADENYLATE CYCLASE; CYCLIC GMP; GLIBENCLAMIDE; GUANYLATE CYCLASE; INDOMETACIN; KT 5720; N(G) NITROARGININE METHYL ESTER; NITRIC OXIDE SYNTHASE; NITRO DERIVATIVE; POTASSIUM CHANNEL; TETRYLAMMONIUM; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; COMPUTER MODEL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING; DRUG INHIBITION; ENZYME ACTIVATION; ENZYME INHIBITION; IN VITRO STUDY; MACROMOLECULE; MALE; NONHUMAN; PRIORITY JOURNAL; PROSTAGLANDIN RELEASE; RAT; VASCULAR RING; VASODILATATION;

ANIMALS; BENZENE DERIVATIVES; CYCLIC GMP; GUANYLATE CYCLASE; MALE; RATS; RATS, WISTAR; RECEPTORS, CYTOPLASMIC AND NUCLEAR; VASODILATOR AGENTS;

EID: 84874108931     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2012.12.012     Document Type: Article

References (47)

1. O.R. Gottlieb, and M.T. Magalhães Occurrence of 1-nitro-2-phenylethane in Ocotea pretiosa and Aniba canelilla J Org Chem 24 1959 2070
2. O.R. Gottlieb Chemosystematics on the Lauraceae Phytochemistry 5 1972 1537 1570
3. M. Matsuo, D.F. Kirkland, and E.W. Underhill 1-Nitro-2-phenylethane: a possible intermediate in the biosynthesis of benzyl glucosinolate Phytochemistry 11 1972 697 701
4. L. Du, and B.A. Halkier Isolation of a microsomal enzyme system involved in glucosinolate biosynthesis from seedlings of Tropaeolum majus L Plant Physiol 111 1996 831 837 (Pubitemid 126450559)
5. U. Wittstock, and B.A. Halkier Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate J Biol Chem 275 2000 14659 14666 (Pubitemid 30339757)
6. D. Tieman, M. Taylor, N. Schauer, A.R. Fernie, A.D. Hanson, and H.J. Klee Tomato aromatic amino acid decarboxylases participate in synthesis of the flavor volatiles 2-phenylethanol and 2-phenylacetaldehyde Proc Natl Acad Sci USA 103 2006 8287 8292 (Pubitemid 43801090)
7. R.J. de Siqueira, F.I. Macedo, L.F. Interaminense, P.J. Magalhães, and T.S. Brito 1-Nitro-2-phenylethane, the main constituent of the essential oil of Aniba canelilla, elicits a vago-vagal bradycardiac and depressor reflex in normotensive rats Eur J. Pharmacol 638 2010 90 98
8. L.F. Interaminense, R.J. de Siqueira, F.E. Xavier, G.P. Duarte, P.J. Magalhães, and J.K. da Silva Cardiovascular effects of 1-nitro-2-phenylethane, the main constituent of the essential oil of Aniba canelilla, in spontaneously hypertensive rats Fundam Clin Pharmacol 25 2011 661 669
9. J. Donnerer, and F. Lembeck Analysis of the effects of intravenously injected capsaicin in the rat Naunyn Schmiedebergs Arch Pharmacol 320 1982 54 57 (Pubitemid 12048310)
10. J.M. Oger, A. Fardeau, H. Guinaudeau, J.P. Bouchara, and A. Fournet Aniba canelilla (H.B.K.) Mez essential oil: analysis of chemical constituents and fugistatic properties J Essent Oil Res 6 1994 493 497
11. S. Lahlou, P.J. Magalhães, R.J. de Siqueira, A.F. Figueiredo, L.F. Interaminense, and J.G. Maia Cardiovascular effects of the essential oil of Aniba canelilla bark in normotensive rats J Cardiovasc Pharmacol 46 2005 412 421 (Pubitemid 41407567)
12. J.K. da Silva, P.J. Sousa, E.H. Andrade, and J.G. Maia Antioxidant capacity and cytotoxicity of essential oil and methanol extract of Aniba canelilla (H.B.K.) Mez J Agric Food Chem 55 2007 9422 9426 (Pubitemid 350205292)
13. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, and R.K. Belew Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function J Comput Chem 19 1998 1639 1662 (Pubitemid 128590223)
14. X. Ma, N. Sayed, A. Beuve, and F. van den Akker NO and CO differentially activate soluble guanylyl cyclase via a heme pivot-bend mechanism EMBO J 26 2007 578 588 (Pubitemid 46160957)
15. M.F. Sanner, B.S. Duncan, C.J. Carrillo, and A.J. Olson Integrating computation and visualization for biomolecular analysis: an example using python and AVS Pac Symp Biocomput 4 1999 392 400
16. M.A. Noguera, and M.P. D'Ocon Different and common intracellular calcium-stores mobilized by noradrenaline and caffeine in vascular smooth muscle Naunyn Schmiedebergs Arch Pharmacol 345 1992 333 341
17. K.L. Christensen, and M.J. Mulvany Location of resistance arteries J Vasc Res 38 2001 1 12 (Pubitemid 32171094)
18. J.E. Niedel, L.J. Kuhn, and G.R. Vandenbark Phorbol diester receptor copurifies with protein kinase C Proc Natl Acad Sci USA 80 1983 36 40 (Pubitemid 13221823)
19. K. Leuner, J.H. Heiser, S. Derksen, M.I. Mladenov, C.J. Fehske, and R. Schubert Simple 2,4-diacylphloroglucinols as classic transient receptor potential-6 activators: identification of a novel pharmacophore Mol Pharmacol 77 2010 368 377
20. L. Levine, P.M. Hinkle, E.F. Voelkel, and A.H. Tashjian Jr. Prostaglandin production by mouse fibrosarcoma cells in culture: inhibition by indomethacin and aspirin Biochem Biophys Res Commun 47 1972 888 896
21. C. Lippe, and C. Ardizzone Actions of vasopressin and isoprenaline on the ionic transport across the isolated frog skin in the presence and the absence of adenyl cyclase inhibitors MDL12330A and SQ22536 Comp Biochem Physiol 99 1991 209 211
22. H. Kase, K. Iwahashi, S. Nakanishi, Y. Matsuda, K. Yamada, and M. Takahashi K-252 compounds, novel and potent inhibitors of protein kinase C and cyclic nucleotide-dependent protein kinases Biochem Biophys Res Commun 142 1987 436 440 (Pubitemid 17003365)
23. J. Garthwaite, E. Southam, C.L. Boulton, E.B. Nielsen, K. Schmidt, and B. Mayer Potent and selective inhibition of nitric oxide-sensitive guanylyl cyclase by 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one Mol Pharmacol 48 1995 184 188
24. C.A. Gruetter, D.Y. Gruetter, J.E. Lyon, P.J. Kadowitz, and L.J. Ignarro Relationship between cyclic guanosine 3′:5′-monophosphate formation and relaxation of coronary arterial smooth muscle by glyceryl trinitrate, nitroprusside, nitrite and nitric oxide: effects of methylene blue and methemoglobin J Pharmacol Exp Ther 219 1981 181 186 (Pubitemid 11018648)
25. 2+ entry in agonist-induced pulmonary vasoconstriction Am J Physiol Lung Cell Mol Physiol 280 2001 L870 L880
26. J.M. Langlands, and J. Diamond The effect of phenylephrine on inositol 1,4,5-trisphosphate levels in vascular smooth muscle measured using a protein binding assay system Biochem Biophys Res Commun 173 1990 1258 1265
27. 2+ store and mitochondria in rat aortic smooth muscle cells Biochem J 357 2001 363 371 (Pubitemid 32701772)
28. ++ release elicited by inositol trisphosphate but not caffeine in rat vascular smooth muscle J Pharmacol Exp Ther 285 1998 16 21 (Pubitemid 28207564)
29. T. Itoh, M. Kajiwara, K. Kitamura, and H. Kuriyama Effects of vasodilator agents on smooth muscle cells of the coronary artery of the pig Br J Pharmacol 74 1981 455 468 (Pubitemid 11006669)
30. O. Pauvert, R. Marthan, and J. Savineau NO-induced modulation of calcium-oscillations in pulmonary vascular smooth muscle Cell Calcium 27 2000 329 338
31. K.S. Ju, and R.E. Parales Nitroaromatic compounds, from synthesis to biodegradation Microbiol Mol Biol Rev 74 2010 250 272
32. J.D. Artz, and G.R. Thatcher NO release from NO donors and nitrovasodilators: comparisons between oxyhemoglobin and potentiometric assays Chem Res Toxicol 11 1998 1393 1397 (Pubitemid 29013610)
33. E. Martin, V. Berka, I. Sharina, and A.L. Tsai Mechanism of binding of NO to soluble guanylyl cyclase: implication for the second NO binding to the heme proximal site Biochemistry 51 2012 2737 2746
34. Y. Minamiyama, S. Takemura, Y. Nishino, and S. Okada Organic nitrate tolerance is induced by degradation of some cytochrome P450 isoforms Redox Rep 7 2002 339 342 (Pubitemid 36032929)
35. O.V. Evgenov, P. Pacher, P.M. Schmidt, G. Haskó, H.H. Schmidt, and J.P. Stasch NO-independent stimulators and activators of soluble guanylate cyclase: discovery and therapeutic potential Nat Rev Drug Discov 5 2006 755 768 (Pubitemid 44323702)
36. P. Wohlfart, T. Malinski, H. Ruetten, U. Schindler, W. Linz, and K. Schoenafinger Release of nitric oxide from endothelial cells stimulated by YC-1, an activator of soluble guanylyl cyclase Br J Pharmacol 128 1999 1316 1322
37. F.B. Priviero, J.S. Baracat, C.E. Teixeira, M.A. Claudino, G. De Nucci, and E. Antunes Mechanisms underlying relaxation of rabbit aorta by BAY 41-2272, a nitric oxide-independent soluble guanylate cyclase activator Clin Exp Pharmacol Physiol 32 2005 728 734 (Pubitemid 41603152)
38. C.E. Teixeira, F.B. Priviero, and R.C. Webb 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 317 2006 258 266
39. D.L. Selwood, D.G. Brummell, J. Budworth, G.E. Burtin, R.O. Campbell, and S.S. Chana Synthesis and biological evaluation of novel pyrazoles and indazoles as activators of the nitric oxide receptor, soluble guanylate cyclase J Med Chem 44 2001 78 93 (Pubitemid 32049785)
40. M. Takagi, H. Mochida, T. Noto, K. Yano, H. Inoue, and T. Ikeo Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum Eur J Pharmacol 411 2001 161 168 (Pubitemid 32013124)
41. J.B. Salom, M.C. Burguete, F.J. Pérez-Asensio, M. Castelló-Ruiz, G. Torregrosa, and E. Alborch Relaxant effect of sildenafil in the rabbit basilar artery Vascul Pharmacol 44 2006 10 16 (Pubitemid 41796965)
42. A.L. Tsai, V. Berka, F. Martin, X. Ma, F. van den Akker, and M. Fabian Is Nostoc H-NOX a NO sensor or redox switch Biochemistry 49 2010 6587 6599
43. M. Lamothe, F.J. Chang, N. Balashova, R. Shirokov, and A. Beuve Functional characterization of nitric oxide and YC-1 activation of soluble guanylyl cyclase: structural implication for the YC-1 binding site Biochemistry 43 2004 3039 3048 (Pubitemid 38352254)
44. J.P. Stasch, E.M. Becker, C. Alonso-Alija, H. Apeler, K. Dembowsky, and A. Feurer NO-independent regulatory site on soluble guanylate cyclase Nature 410 2001 212 215 (Pubitemid 32216593)
45. 1 subunit of soluble guanylyl cyclase is necessary for activation of the enzyme by nitric oxide and YC-1 but is not involved in heme binding J Biol Chem 278 2003 12590 12597 (Pubitemid 36800249)
46. S.H. Francis, J.L. Busch, J.D. Corbin, and D. Sibley cGMP-dependent protein kinases and cGMP phosphodiesterases in nitric oxide and cGMP action Pharmacol Rev 62 2010 525 563
47. M. Morgado, E. Cairrão, A.J. Santos-Silva, and I. Verde Cyclic nucleotide-dependent relaxation pathways in vascular smooth muscle Cell Mol Life Sci 69 2012 247 266