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Doctorovich, F.; Bikiel, D.E.; Pellegrino, J.; Suárez, S.A.; Martí, M.A. "Azanone (HNO) interaction with Hemeproteins and metalloporphyrins" (2012) Advances in Inorganic Chemistry. 64:97-139
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Abstract:

Azanone (HNO), also called nitroxyl, is a highly reactive compound, with interesting yet poorly understood biological properties. Like its closely related sibling NO, its main biological targets are heme proteins, although significant differences in their reactivity and pharmacological effects are observed. Due to its high reactivity, azanone studies rely on the use of donors, molecules that therefore offer interesting therapeutic perspectives. In this review, we firstly describe the pharmacological potential of azanone, the chemistry of the available donors, and the main biological relevant HNO reactions with special focus on heme proteins and metalloporphyrins (Fe, Mn, and Co). Finally, we present evidence concerning the endogenous . in vivo azanone production hypothesis, and how the recent porphyrin-based developed methods for its detection may contribute to solve this key physiological question. © 2012 Elsevier Inc.

Registro:

Documento: Artículo
Título:Azanone (HNO) interaction with Hemeproteins and metalloporphyrins
Autor:Doctorovich, F.; Bikiel, D.E.; Pellegrino, J.; Suárez, S.A.; Martí, M.A.
Filiación:Departamento de Química Inorgánica, Analítica y Química Física, INQUIMAE-CONICET, Buenos Aires, Argentina
Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II (1428), Buenos Aires, Argentina
Palabras clave:Azanone; Cobalt; Heme; HNO; Iron; Kinetics; Manganese; Myoglobin; Nitrosyl; Nitroxyl; Nitroxyl anion; NO; NOS; Oxidation; Porphyrin; Protein; Reductive nitrosylation; Ruthenium
Año:2012
Volumen:64
Página de inicio:97
Página de fin:139
DOI: http://dx.doi.org/10.1016/B978-0-12-396462-5.00004-0
Título revista:Advances in Inorganic Chemistry
Título revista abreviado:Adv. Inorg. Chem.
ISSN:08988838
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08988838_v64_n_p97_Doctorovich

Referencias:

  • Doctorovich, F., (2011) Coord. Chem. Rev., 255. , (23-24), 2764-2784
  • Bruna, P., (1979) Chem. Phys. Lett., 67, pp. 109-114
  • Guadagnini, R., Schatz, G.C., Walch, S.P., (1995) J. Chem. Phys., 102, p. 774
  • Luna, A., Merch, M., Srn, B., Roos, O., (1995) Chem. Phys., 196, pp. 437-445
  • Moncada, S., Palmer, R.M., Higgs, E.A., (1991) Pharmacol. Rev., 43, pp. 109-142
  • Ignarro, L.J., (1996) Kidney Int., 49 (SUPPL. 55), pp. S2
  • Miranda, K.M., (2003) Proc. Natl. Acad. Sci. USA, 100, pp. 9196-9201
  • Switzer, C.H., (2009) Biochim. Biophys. Acta, 1787, pp. 835-840
  • Paolocci, N., (2007) Pharmacol. Ther., 113, pp. 442-458
  • Miranda, K.M., Nagasawa, H.T., Toscano, J.P., (2005) Curr. Top. Med. Chem., 5, pp. 649-664
  • Ma, X.L., (1999) Proc. Natl. Acad. Sci. USA, 96, p. 14617
  • Tocchetti, C.G., (2007) Circ. Res., 100, pp. 96-104
  • Lancel, S., (2009) Circ. Res., 104, pp. 720-723
  • Ma, X.L., Weyrich, A.S., Lefer, D.J., Lefer, A.M., (1993) Circ. Res., 72, pp. 403-412
  • Adak, S., Wang, Q., Stuehr, D.J., (2000) J. Biol. Chem., 275, pp. 33554-33561
  • Schmidt, H.H., (1996) Proc. Natl. Acad. Sci. USA, 93, pp. 14492-14497
  • Feelisch, M., Te Poel, M., Zamora, R., Deussen, A., Moncada, S., (1994) Nature, 368, pp. 62-65
  • Ishimura, Y., (2005) Biochem. Biophys. Res. Commun., 338, pp. 543-549
  • Hobbs, A.J., Fukuto, J.M., Ignarro, L.J., (1994) Proc. Natl. Acad. Sci. USA, 91, pp. 10992-10996
  • Woodward, J.J., Nejatyjahromy, Y., Britt, R.D., Marletta, M.A., (2010) J. Am. Chem. Soc., 132, pp. 5105-5113
  • Stoll, S., (2010) J. Am. Chem. Soc., 132, pp. 11812-11823
  • Donzelli, S., (2006) Free Radic. Biol. Med., 40, pp. 1056-1066
  • Donzelli, S., (2008) Free Radic. Biol. Med., 45, pp. 578-584
  • Bari, S.E., Amorebieta, V.T., Gutiérrez, M.M., Olabe, J., Doctorovich, F., (2010) J. Inorg. Biochem., 104, pp. 30-36
  • Niketic, V., Stojanovic, S., Nikolic, A., Michelson, A.M., (1999) Free Radic. Biol. Med., 27, pp. 992-996
  • Stoyanovsky, D.A., (2005) J. Am. Chem. Soc., 127, pp. 15815-15823
  • Miranda, K.M., (2005) Coord. Chem. Rev., 249, pp. 433-455
  • Bartberger, M.D., Fukuto, J.M., Houk, K.N., (2001) Proc. Natl. Acad. Sci. USA, 98, pp. 2194-2198
  • Veprek-Siska, J., Pliska, V., Smirous, F., Visely, F., (1959) Collect. Czech. Chem. Commun., 24, pp. 687-693
  • Hughes, M.N., Wimbledon, P.E., (1975) Chem. Ind., pp. 742-743
  • Maragos, C.M., (1991) J. Med. Chem., 34, pp. 3242-3247
  • Bonner, F.T., Ravid, B., (1975) Inorg. Chem., 14, pp. 558-563
  • Hughes, M.N., Wimbledon, P.E., (1976) J. Chem. Soc. Dalton Trans., 8, pp. 703-707
  • Porcheddu, A., De Luca, L., Giacomelli, G., (2009) Synlett, 2009, pp. 2149-2153
  • Bonner, F.T., Ko, Y.H., (1992) Inorg. Chem., 31, pp. 2514-2519
  • Seel, F., Bliefert, C., (1972) Z. Anorg. Allg. Chem., 394, pp. 187-196
  • Shafirovich, V., Lymar, S.V., (2002) Proc. Natl. Acad. Sci. USA, 99, pp. 7340-7345
  • Buchholz, J.R., Powell, R.E., (1963) J. Am. Chem. Soc., 85, pp. 509-511
  • Liochev, S.I., Fridovich, I., (2003) Free Radic. Biol. Med., 34, pp. 1399-1404
  • Lymar, S.V., Shafirovich, V., Poskrebyshev, G.A., (2005) Inorg. Chem., 44, pp. 5212-5221
  • Lymar, S.V., Shafirovich, V., (2007) J. Phys. Chem. B, 111, pp. 6861-6867
  • Goldstein, S., Czapski, G., (1995) Free Radic. Biol. Med., 19, pp. 505-510
  • Huie, R.E., Padmaja, S., (1993) Free Radic. Res. Commun., 18, pp. 195-199
  • Goldstein, S., Czapski, G., (1996) J. Am. Chem. Soc., 118, pp. 3419-3425
  • Smallwood, H.M., (1929) J. Am. Chem. Soc., 51, pp. 1985-1999
  • King, S., Nagasawa, H., (1999) Methods Enzymol., 301, p. 211
  • Orgel, L.E., (1953) J. Chem. Soc., pp. 1276-1278
  • Walsh, A.D., (1953) J. Chem. Soc., pp. 2288-2296
  • Bartberger, M.D., (2002) Proc. Natl. Acad. Sci. USA, 99, pp. 10958-10963
  • Szmytkowski, C., Maciag, K., (1991) J. Phys. B Atom. Mol. Phys., 24, p. 4273
  • Tennyson, J., Noble, C., (1986) J. Phys. B: At. Mol. Phys., 19, p. 4025
  • Martí, M.A., Bari, S.E., Estrin, D.A., Doctorovich, F., (2005) J. Am. Chem. Soc., 127, pp. 4680-4684
  • Suárez, S.A., (2007) Polyhedron, 26, pp. 4673-4679
  • Bari, S.E., Martí, M.A., Amorebieta, V.T., Estrin, D.A., Doctorovich, F., (2003) J. Am. Chem. Soc., 125, pp. 15272-15273
  • Kohout, F.C., Lampe, F.W., (1965) J. Am. Chem. Soc., 87, p. 5795
  • Smith, P.A.S., Hein, G.E., (1960) J. Am. Chem. Soc., 82, pp. 5731-5740
  • Buchholz, J.R., Powell, R.E., (1965) J. Am. Chem. Soc., 87, pp. 2350-2353
  • Bonner, F.T., Dzelzkalns, L.S., Bonucci, J.A., (1978) Inorg. Chem., 17, pp. 2487-2494
  • Smith, A.L., Johnston, H.L., (1952) J. Am. Chem. Soc., 74, pp. 4696-4698
  • Bryukov, M.G., (1993) Chem. Phys. Lett., 208, pp. 392-398
  • Ford, P.C., (2010) Inorg. Chem., 49, pp. 6226-6239
  • Hoshino, M., Laverman, L., Ford, P.C., (1999) Coord. Chem. Rev., 187, pp. 75-102
  • Kadish, K.M., (2000) The Porphyrin Handbook, , Academic Press, Boston
  • Richter-Addo, G.B., Legzdins, P., (1992) Metal Nitrosyls, , Oxford University, New York
  • Enemark, J.H., Feltham, R.D., (1974) J. Am. Chem. Soc., 96, pp. 5002-5004
  • Westcott, B.L., Enemark, J.H., (1999) Inorganic Electronic Structure and Spectroscopy, , John Wiley & Sons, New York
  • Enemark, J.H., Feltham, R.D., (1974) Coord. Chem. Rev., 13, pp. 339-406
  • Wyllie, G.R.A., Scheidt, W.R., (2002) Chem. Rev., 102, pp. 1067-1090
  • Pellegrino, J., Bari, S.E., Bikiel, D.E., Doctorovich, F., (2010) J. Am. Chem. Soc., 132, pp. 989-995
  • Laverman, L.E., Ford, P.C., (2001) J. Am. Chem. Soc., 123, pp. 11614-11622
  • Wayland, B.B., Olson, L.W., (1974) J. Am. Chem. Soc., 96, pp. 6037-6041
  • Hoshino, M., Maeda, M., Konishi, R., Seki, H., Ford, P.C., (1996) J. Am. Chem. Soc., 118, pp. 5702-5707
  • Spasojevic, I., Batini-Haberle, I., Fridovich, I., (2000) Nitric Oxide, 4, pp. 526-533
  • Zahran, Z.N., Lee, J., Alguindigue, S.S., Khan, M.A., Richter-Addo, G.B., (2004) Dalton Trans., pp. 44-50
  • Scheidt, W.R., Hoard, J.L., (1973) J. Am. Chem. Soc., 95, pp. 8281-8288
  • Roncaroli, F., Eldik, R.V., (2006) J. Am. Chem. Soc., 128, pp. 8042-8053
  • Schopfer, M.P., Wang, J., Karlin, K.D., (2010) Inorg. Chem., 49, pp. 6267-6282
  • Blomberg, M.R.A., Siegbahn, P.E.M., (2006) Biochim. Biophys. Acta, 1757, pp. 969-980
  • Praneeth, V.K.K., Näther, C., Peters, G., Lehnert, N., (2006) Inorg. Chem., 45, pp. 2795-2811
  • Collman, J.P., (2008) J. Am. Chem. Soc., 130, pp. 16498-16499
  • Collman, J.P., (2008) Proc. Natl. Acad. Sci. USA, 105, pp. 15660-15665
  • Suárez, S.A., (2010) Inorg. Chem., 49, pp. 6955-6966
  • Whitten, D.G., Baker, E.W., Corwin, A.H., (1963) J. Org. Chem., 28, pp. 2363-2368
  • Kumar, M.R., Fukuto, J.M., Miranda, K.M., Farmer, P.J., (2010) Inorg. Chem., 49, pp. 6283-6292
  • Shiro, Y., (1995) J. Biol. Chem., 270, p. 1617
  • Shiro, Y., (1995) Biochemistry, 34, pp. 9052-9058
  • Lin, R., Farmer, P.J., (2000) J. Am. Chem. Soc., 122, pp. 2393-2394
  • Sulc, F., Immoos, C.E., Pervitsky, D., Farmer, P.J., (2004) J. Am. Chem. Soc., 126, pp. 1096-1101
  • Miranda, K.M., (2003) J. Inorg. Biochem., 93, pp. 52-60
  • Bazylinski, D.A., Hollocher, T.C., (1985) J. Am. Chem. Soc., 107, pp. 7982-7986
  • Bazylinski, D.A., Goretski, J., Hollocher, T.C., (1985) J. Am. Chem. Soc., 107, pp. 7986-7989
  • Dutton, A.S., Fukuto, J.M., Houk, K.N., (2004) J. Am. Chem. Soc., 126, pp. 3795-3800
  • Denninger, J.W., Marletta, M.A., (1999) Biochim. Biophys. Acta, 1411, pp. 334-350
  • Poulos, T.L., (2006) Curr. Opin. Struct. Biol., 16, pp. 736-743
  • Hobbs, A.J., Ignarro, L.J., (1996) Methods Enzymol., 269, pp. 134-148
  • Capece, L., Estrin, D.A., Marti, M.A., (2008) Biochemistry, 47, pp. 9416-9427
  • Miller, T.W., (2009) J. Biol. Chem., 284, pp. 21788-21796
  • Dierks, E.A., Burstyn, J.N., (1996) Biochem. Pharmacol., 51, pp. 1593-1600
  • Wilkins, P.C., Jacobs, H.K., Johnson, M.D., Gopalan, A.S., (2004) Inorg. Chem., 43, p. 7877
  • Koppenol, W., Moreno, J., Pryor, W.A., Ischiropoulos, H., Beckman, J., (1992) Chem. Res. Toxicol., 5, pp. 834-842
  • Sharma, V.S., Isaacson, R.A., John, M.E., Waterman, M.R., Chevion, M., (1983) Biochemistry, 22, p. 3897
  • Boron, I., Suárez, S.A., Doctorovich, F., Martí, M.A., Bari, S.E., (2011) J. Inorg. Biochem., 105, pp. 1044-1049
  • Scott, E.E., Gibson, Q.H., Olson, J.S., (2001) J. Biol. Chem., 276, pp. 5177-5188
  • Averill, B.A., (1996) Chem. Rev., 96, pp. 2951-2964
  • Einsle, O., Messerschmidt, A., Huber, R., Kroneck, P.M.H., Neese, F., (2002) J. Am. Chem. Soc., 124, pp. 11737-11745
  • Simon, J., (2002) FEMS Microbiol. Rev., 26, pp. 285-309
  • Daiber, A., (2002) J. Inorg. Biochem., 88, pp. 343-352
  • Farmer, P.J., Sulc, F., (2005) J. Inorg. Biochem., 99, pp. 166-184
  • Farmer, P.J., Kumar, M.R., Almaraz, E., (2010) Comments Inorg. Chem., 31, pp. 130-143
  • Kumar, M.R., (2009) Biochemistry, 48, pp. 5018-5025
  • Lee, J., Richter-Addo, G.B., (2004) J. Inorg. Biochem., 98, pp. 1247-1250
  • Choi, I.K., Liu, Y., Feng, D., Paeng, K.J., Ryan, M.D., (1991) Inorg. Chem., 30, pp. 1832-1839
  • Serres, R.G., (2004) J. Am. Chem. Soc., 126, pp. 5138-5153
  • Montenegro, A.C., (2009) Angew. Chem. Int. Ed Engl., 48, pp. 4213-4216
  • Lehnert, N., Praneeth, V., Paulat, F., (2006) J. Comput. Chem., 27, pp. 1338-1351
  • Mason, J., Larkworthy, L.F., Moore, E.A., (2002) Chem. Rev., 102, pp. 913-934
  • Sulc, F., Fleischer, E., Farmer, P.J., Ma, D., La Mar, G.N., (2003) J. Biol. Inorg. Chem., 8, pp. 348-352
  • Immoos, C.E., (2005) J. Am. Chem. Soc., 127, pp. 814-815
  • Sellmann, D., Gottschalk-Gaudig, T., Häußinger, D., Heinemann, F.W., Hess, B.A., (2001) Chem. Eur. J., 7, pp. 2099-2103
  • Marchenko, A.V., (2002) Inorg. Chem., 41, pp. 4087-4089
  • Pervitsky, D., Immoos, C., Veer, W.V.D., Farmer, P.J., (2007) J. Am. Chem. Soc., 129, pp. 9590-9591
  • Einsle, O., (1999) Nature, 400, pp. 476-480
  • Richardson, D.J., Watmough, N.J., (1999) Curr. Opin. Chem. Biol., 3, pp. 207-219
  • Ferguson, S.J., (1998) Curr. Opin. Chem. Biol., 2, pp. 182-193
  • Moura, I., Moura, J.J., (2001) Curr. Opin. Chem. Biol., 5, pp. 168-175
  • Fujii, M., (1995) J. Biol. Chem., 270, pp. 1617-1623
  • Obayashi, E., Takahashi, S., Shiro, Y., (1998) J. Am. Chem. Soc., 120, pp. 12964-12965
  • Harris, D.L., (2002) Int. J. Quantum Chem., 88, pp. 183-200
  • Vincent, M., Hillier, I., Ge, J., (2005) Chem. Phys. Lett., 407, pp. 333-336
  • Linder, D.P., Rodgers, K.R., (2005) Inorg. Chem., 44, pp. 8259-8264
  • Ling, Y., Mills, C., Weber, R., Yang, L., Zhang, Y., (2010) J. Am. Chem. Soc., 132, pp. 1583-1591
  • Dobmeier, K.P., Riccio, D.A., Schoenfisch, M.H., (2008) Anal. Chem., 80, pp. 1247-1254
  • Guillaud, G., (1998) Coord. Chem. Rev., pp. 1433-1484
  • Davies, I.R., Zhang, X., (2008) Methods Enzymol., 436, pp. 63-95
  • Richter-Addo, G.B., (1996) Inorg. Chem., 35, pp. 6530-6538
  • Irvine, J.C., (2008) Trends Pharmacol. Sci., 29, pp. 601-608
  • Bikiel, D.E., (2006) Phys. Chem. Chem. Phys., 8, pp. 5611-5628
  • Doyle, M.P., Mahapatro, S.N., Broene, R.D., Guy, J.K., (1988) J. Am. Chem. Soc., 110, pp. 593-599
  • Rosenthal, J., Lippard, S.J., (2010) J. Am. Chem. Soc., 132, pp. 5536-5537
  • Tennyson, A.G., Do, L., Smith, R.C., Lippard, S.J., (2007) Nitric Oxide, 26, pp. 4625-4630
  • Batinic-Haberle, I., (1999) Inorg. Chem., 38, pp. 4011-4022
  • Choi, E.-Y., (2007) Langmuir, 23, pp. 10389-10394

Citas:

---------- APA ----------
Doctorovich, F., Bikiel, D.E., Pellegrino, J., Suárez, S.A. & Martí, M.A. (2012) . Azanone (HNO) interaction with Hemeproteins and metalloporphyrins. Advances in Inorganic Chemistry, 64, 97-139.
http://dx.doi.org/10.1016/B978-0-12-396462-5.00004-0
---------- CHICAGO ----------
Doctorovich, F., Bikiel, D.E., Pellegrino, J., Suárez, S.A., Martí, M.A. "Azanone (HNO) interaction with Hemeproteins and metalloporphyrins" . Advances in Inorganic Chemistry 64 (2012) : 97-139.
http://dx.doi.org/10.1016/B978-0-12-396462-5.00004-0
---------- MLA ----------
Doctorovich, F., Bikiel, D.E., Pellegrino, J., Suárez, S.A., Martí, M.A. "Azanone (HNO) interaction with Hemeproteins and metalloporphyrins" . Advances in Inorganic Chemistry, vol. 64, 2012, pp. 97-139.
http://dx.doi.org/10.1016/B978-0-12-396462-5.00004-0
---------- VANCOUVER ----------
Doctorovich, F., Bikiel, D.E., Pellegrino, J., Suárez, S.A., Martí, M.A. Azanone (HNO) interaction with Hemeproteins and metalloporphyrins. Adv. Inorg. Chem. 2012;64:97-139.
http://dx.doi.org/10.1016/B978-0-12-396462-5.00004-0