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?
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 pr...
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| Otros Autores: | , , , , , , , , , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
American Chemical Society
2015
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| Sumario: | 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. |
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| Bibliografía: | 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 |
| ISSN: | 00027863 |
| DOI: | 10.1021/ja512343w |