Navegar

Colección

Datos Estadísticas

Artículo

Suarez, S.A.; Neuman, N.I.; Muñoz, M.; Álvarez, L.; Bikiel, D.E.; Brondino, C.D.; Ivanović-Burmazović, I.; Miljkovic, J.L.; Filipovic, M.R.; Martí, M.A.; Doctorovich, F. "Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?" (2015) Journal of the American Chemical Society. 137(14):4720-4727
El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The role of NO in biology is well established. However, an increasing body of evidence suggests that azanone (HNO), could also be involved in biological processes, some of which are attributed to NO. In this context, one of the most important and yet unanswered questions is whether and how HNO is produced in vivo. A possible route concerns the chemical or enzymatic reduction of NO. In the present work, we have taken advantage of a selective HNO sensing method, to show that NO is reduced to HNO by biologically relevant alcohols with moderate reducing capacity, such as ascorbate or tyrosine. The proposed mechanism involves a nucleophilic attack to NO by the alcohol, coupled to a proton transfer (PCNA: proton-coupled nucleophilic attack) and a subsequent decomposition of the so-produced radical to yield HNO and an alkoxyl radical. (Graph Presented). © 2015 American Chemical Society.

Registro:

Documento: Artículo
Título:Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?
Autor:Suarez, S.A.; Neuman, N.I.; Muñoz, M.; Álvarez, L.; Bikiel, D.E.; Brondino, C.D.; Ivanović-Burmazović, I.; Miljkovic, J.L.; Filipovic, M.R.; Martí, M.A.; Doctorovich, F.
Filiación:Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, C1428EGA, Argentina
Departamento de Física, Facultad de Bioquímica y Ciencias Biológicas, Universidad Nacional Del Litoral, Paraje El Pozo, Santa Fe, 3000, Argentina
Department of Chemistry and Pharmacy, Friedrich-Alexander University Erlangen-Nuremberg, Egerlandstrasse 1, Erlangen, 91058, Germany
Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, Buenos Aires, C1428EGA, Argentina
Palabras clave:Nitric oxide; Alkoxyl radicals; Biological media; Biological process; Enzymatic reduction; In-vivo; Nucleophilic attack; Reducing capacity; Amino acids; alcohol derivative; ascorbic acid; azanone; inducible nitric oxide synthase; nitric oxide; nitric oxide donor; tyrosine; unclassified drug; alcohol derivative; alkoxyl radical; ascorbic acid; nitric oxide; nitrogen oxide; nitroxyl; tyrosine; animal cell; aqueous solution; Article; Bovinae; controlled study; decomposition; dimerization; electron spin resonance; endothelium cell; immunocompetent cell; in vitro study; kinetics; macrophage; nerve cell; nonhuman; nuclear magnetic resonance spectroscopy; nucleophilicity; oxidation reduction potential; proton coupled nucleophilic attack; proton transport; reaction analysis; reduction; tautomer; animal; bovine; chemistry; metabolism; oxidation reduction reaction; Alcohols; Animals; Ascorbic Acid; Cattle; Endothelial Cells; Nitric Oxide; Nitrogen Oxides; Oxidation-Reduction; Tyrosine
Año:2015
Volumen:137
Número:14
Página de inicio:4720
Página de fin:4727
DOI: http://dx.doi.org/10.1021/ja512343w
Título revista:Journal of the American Chemical Society
Título revista abreviado:J. Am. Chem. Soc.
ISSN:00027863
CODEN:JACSA
CAS:ascorbic acid, 134-03-2, 15421-15-5, 50-81-7; inducible nitric oxide synthase, 501433-35-8; nitric oxide, 10102-43-9; tyrosine, 16870-43-2, 55520-40-6, 60-18-4; nitrogen oxide, 11104-93-1; Alcohols; alkoxyl radical; Ascorbic Acid; Nitric Oxide; Nitrogen Oxides; nitroxyl; Tyrosine
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v137_n14_p4720_Suarez

Referencias:

  • Napoli, C., Paolisso, G., Casamassimi, A., Al-Omran, M., Barbieri, M., Sommese, L., Infante, T., Ignarro, L.J., (2013) J. Am. Coll. Cardiol., 62, p. 89
  • Tonzetich, Z.J., McQuade, L.E., Lippard, S.J., (2010) Inorg. Chem., 49, p. 6338
  • Goodrich, L.E., Paulat, F., Praneeth, V.K.K., Lehnert, N., Arbor, A., (2010) Biochemistry, p. 6293
  • Martínez-Ruiz, A., Cadenas, S., Lamas, S., (2011) Free Radic. Biol. Med., 51, p. 17
  • Bruce King, S., (2013) Free Radic. Biol. Med., 55, p. 1
  • Irvine, J.C., Ritchie, R.H., Favaloro, J.L., Andrews, K.L., Widdop, R.E., Kemp-Harper, B.K., (2008) Trends Pharmacol. Sci., 29, p. 601
  • Flores-Santana, W., Salmon, D.J., Donzelli, S., Switzer, C.H., Basudhar, D., Ridnour, L., Cheng, R., Wink, D.A., (2011) Antioxid. Redox Signal., 14, p. 1659
  • Miranda, K.M., (2005) Coord. Chem. Rev., 249, p. 433
  • Shafirovich, V., Lymar, S.V., (2002) Proc. Natl. Acad. Sci. U.S.A., 99, p. 7340
  • Lymar, S.V., Shafirovich, V., Poskrebyshev, G.A., (2005) Inorg. Chem., 44, p. 5212
  • Miranda, K.M., Nims, R.W., Thomas, D.D., Espey, M.G., Citrin, D., Bartberger, M.D., Paolocci, N., Wink, D.A., (2003) J. Inorg. Biochem., 93, p. 52
  • Liochev, S., (2003) Free Radic. Biol. Med., 34, p. 1399
  • Bartberger, M.D., Fukuto, J.M., Houk, K.N., (2001) Proc. Natl. Acad. Sci. U.S.A., 98, p. 2194
  • Ford, P.C., (2010) Inorg. Chem., 49, p. 6226
  • Hoshino, M., Laverman, L., Ford, P.C., (1999) Coord. Chem. Rev., 187, p. 75
  • Cline, M.R., Tu, C., Silverman, D.N., Toscano, J.P., (2011) Free Radic. Biol. Med., 50, p. 1274
  • Reisz, J.A., Zink, C.N., King, S.B., (2011) J. Am. Chem. Soc., 133, p. 11675
  • Donzelli, S., Espey, M.G., Flores-Santana, W., Switzer, C.H., Yeh, G.C., Huang, J., Stuehr, D.J., Wink, D.A., (2008) Free Radic. Biol. Med., 45, p. 578
  • Suárez, S.A., Martí, M.A., De Biase, P.M., Estrin, D.A., Bari, S.E., Doctorovich, F., (2007) Polyhedron, 26, p. 4673
  • Dobmeier, K.P., Riccio, D.A., Schoenfisch, M.H., (2008) Anal. Chem., 80, p. 1247
  • Martí, M.A., Bari, S.E., Estrin, D.A., Doctorovich, F., (2005) J. Am. Chem. Soc., 127, p. 4680
  • Zhou, Y., Liu, K., Li, J.-Y., Fang, Y., Zhao, T.-C., Yao, C., (2011) Org. Lett., 13, p. 2357
  • Doctorovich, F., Bikiel, D., Pellegrino, J., Suárez, S.A., Larsen, A., Martí, M.A., (2011) Coord. Chem. Rev., 255, p. 2764
  • Tennyson, A.G., Do, L., Smith, R.C., Lippard, S.J., (2006) Nitric Oxide, 26, p. 1
  • Rosenthal, J., Lippard, S.J., (2010) J. Am. Chem. Soc., 132, p. 5536
  • Wrobel, A.T., Johnstone, T.C., Liang, A.D., Lippard, S.J., Rivera-Fuentes, P., (2014) J. Am. Chem. Soc., 136, p. 4697
  • Suárez, S.A., Fonticelli, M.H., Rubert, A.A., De La Llave, E., Scherlis, D., Salvarezza, R.C., Martí, M.A., Doctorovich, F., (2010) Inorg. Chem., 49, p. 6955
  • Suárez, S., Bikiel, D., Wetzler, D., Martí, M.A., Doctorovich, F., (2013) Anal. Chem., 85, pp. 10262-10269
  • Sirsalmath, K., Suárez, S.A., Bikiel, D.E., Doctorovich, F., (2013) J. Inorg. Biochem., 118, p. 134
  • Filipovic, M.R., Eberhardt, M., Prokopovic, V., Mijuskovic, A., Orescanin-Dusic, Z., Reeh, P., Ivanovic-Burmazovic, I., (2013) J. Med. Chem., 56, p. 1499
  • Eberhardt, M., Dux, M., Namer, B., Miljkovic, J., Cordasic, N., Will, C., Kichko, T.I., Filipovic, M.R., (2014) Nat. Commun., 5, p. 4381
  • Fukuto, J.M., Cisneros, C.J., Kinkade, R.L., (2013) J. Inorg. Biochem., 118, p. 201
  • Miranda, K.M., Paolocci, N., Katori, T., Thomas, D.D., Ford, E., Bartberger, M.D., Espey, M.G., Wink, D.A., (2003) Proc. Natl. Acad. Sci. U.S.A., 100, p. 9196
  • Paolocci, N., Saavedra, W.F., Miranda, K.M., Martignani, C., Isoda, T., Hare, J.M., Espey, M.G., Kass, D.A., (2001) Proc. Natl. Acad. Sci. U.S.A., 98, p. 10463
  • Adak, S., Wang, Q., Stuehr, D.J., (2000) J. Biol. Chem., 275, p. 33554
  • Schmidt, H.H.H.W., Hofmann, H., Schindler, U., Shutenko, Z.S., Cunningham, D.D., Feelisch, M., (1996) Proc. Natl. Acad. Sci. U.S.A., 93, p. 14492
  • Feelisch, M., Te Poel, M., Zamora, R., Deussen, A., Moncada, S., (1994) Nature, 368, p. 62
  • Rousseau, D.L., Li, D., Couture, M., Yeh, S.-R., (2005) J. Inorg. Biochem., 99, p. 306
  • Ishimura, Y., Gao, Y.T., Panda, S.P., Roman, L.J., Masters, B.S.S., Weintraub, S.T., (2005) Biochem. Biophys. Res. Commun., 338, p. 543
  • Sabat, J., Egawa, T., Lu, C., Stuehr, D.J., Gerfen, G.J., Rousseau, D.L., Yeh, S.-R., (2013) J. Biol. Chem., 288, p. 6095
  • Li, D., Kabir, M., Stuehr, D.J., Rousseau, D.L., Yeh, S.-R., (2007) J. Am. Chem. Soc., 129, p. 6943
  • Donzelli, S., Graham, M., Flores-Santana, W., Switzer, C.H., Yeh, G.C., Huang, J., Stuehr, D.J., Espey, M.G., (2008) Free Radic. Biol. Med., 45, p. 578
  • Kytzia, A., Korth, H., Sustmann, R., Groot, H., De Kirsch, M., (2006) Chem. - Eur. J., p. 8786
  • Armstrong, D.A., Huie, R.E., Lymar, S., Koppenol, W.H., Merényi, G., Neta, P., Stanbury, D.M., Wardman, P., (2013) Bioinorg. React. Mech., 9, p. 59
  • Filipovic, M.R.M., Miljkovic, J.L.J., Nauser, T., Royzen, M., Klos, K., Shubina, T., Koppenol, W.H., Ivanovic, I., (2012) J. Am. Chem. Soc., 134, p. 12016
  • Miljkovic, J.L., Kenkel, I., Ivanović-Burmazović, I., Filipovic, M.R., (2013) Angew. Chem., Int. Ed., 52, p. 12061
  • Clyne, M.A.A., Thrush, B.A., (1961) Trans. Faraday Soc., 57, p. 1305
  • Cashion, J.K., Polanyi, J.C., (1959) J. Chem. Phys., 30, p. 317
  • Strausz, O.P., Gunning, H.E., (1964) Trans. Faraday Soc., 60, p. 347
  • Kohout, F.C., Lampe, F.W., (1965) J. Am. Chem. Soc., 87, p. 5795
  • Miranda, K.M., Paolocci, N., Katori, T., Thomas, D.D., Ford, E., Bartberger, M.D., Espey, M.G., Wink, D.A., (2003) Proc. Natl. Acad. Sci. U.S.A., 100, p. 9196
  • Porcheddu, A., De Luca, L., Giacomelli, G., (2009) Synlett, 13, p. 2149
  • Heinecke, J.L., Khin, C., Pereira, J.C.M., Suárez, S.A., Iretskii, A.V., Doctorovich, F., Ford, P.C., (2013) J. Am. Chem. Soc., 135, p. 4007
  • Álvarez, L., Suarez, S.A., Bikiel, D.E., Reboucas, J.S., Batinić-Haberle, I., Martí, M.A., Doctorovich, F., (2014) Inorg. Chem., 53, p. 7351
  • Spasojevic, I., Batini-Haberle, I., Fridovich, I., (2000) Nitric Oxide, 4, p. 526
  • Benon, H.J., Bielski, A., Allen, O., Schwarz, H.A., (1981) J. Am. Chem. Soc., 103, p. 3516
  • Kirsch, M., Büscher, A.-M., Aker, S., Schulz, R., De Groot, H., (2009) Org. Biomol. Chem., 7, p. 1954
  • Poderoso, J.J., Carreras, M.C., Schöpfer, F., Lisdero, C.L., Riobó, N.A., Giulivi, C., Boveris, A.D., Cadenas, E., (1999) Free Radic. Biol. Med., 26, p. 925
  • Heinecke, J., Ford, P.C., (2010) Coord. Chem. Rev., 254, p. 235
  • Van Der Zee, J., Van Den Broek, P.J.A., (1998) Free Radic. Biol. Med., 25, p. 282
  • Yenes, S., Messeguer, A., (1999) Tetrahedron, 55, p. 14111
  • May, J.M., (2000) Free Radic. Biol. Med., 28, p. 1421
  • Liu, X., Miller, M.J., Joshi, M.S., Thomas, D.D., Lancaster, J.R., (1998) Proc. Natl. Acad. Sci. U.S.A., 95, p. 2175
  • Kamga, C., Krishnamurthy, S., Shiva, S., (2012) Nitric Oxide, 26, p. 251
  • Gupta, K.J., Igamberdiev, A.U., Manjunatha, G., Segu, S., Moran, J.F., Neelawarne, B., Bauwe, H., Kaiser, W.M., (2011) Plant Sci., 181, p. 520
  • Shiva, S., Huang, Z., Grubina, R., Sun, J., Ringwood, L.A., MacArthur, P.H., Xu, X., Gladwin, M.T., (2007) Circ. Res., 100, p. 654
  • Chouchani, E.T., Methner, C., Nadtochiy, S.M., Logan, A., Pell, V.R., Ding, S., James, A.M., Murphy, M.P., (2013) Nat. Med., 19, p. 753

Citas:

---------- APA ----------
Suarez, S.A., Neuman, N.I., Muñoz, M., Álvarez, L., Bikiel, D.E., Brondino, C.D., Ivanović-Burmazović, I.,..., Doctorovich, F. (2015) . Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?. Journal of the American Chemical Society, 137(14), 4720-4727.
http://dx.doi.org/10.1021/ja512343w
---------- CHICAGO ----------
Suarez, S.A., Neuman, N.I., Muñoz, M., Álvarez, L., Bikiel, D.E., Brondino, C.D., et al. "Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?" . Journal of the American Chemical Society 137, no. 14 (2015) : 4720-4727.
http://dx.doi.org/10.1021/ja512343w
---------- MLA ----------
Suarez, S.A., Neuman, N.I., Muñoz, M., Álvarez, L., Bikiel, D.E., Brondino, C.D., et al. "Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?" . Journal of the American Chemical Society, vol. 137, no. 14, 2015, pp. 4720-4727.
http://dx.doi.org/10.1021/ja512343w
---------- VANCOUVER ----------
Suarez, S.A., Neuman, N.I., Muñoz, M., Álvarez, L., Bikiel, D.E., Brondino, C.D., et al. Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?. J. Am. Chem. Soc. 2015;137(14):4720-4727.
http://dx.doi.org/10.1021/ja512343w