A microscopic study of the deoxyhemoglobin-catalyzed generation of nitric oxide from nitrite anion
There is recent evidence suggesting that nitrite anion (NO2 -) represents the major intravascular NO storage molecule whose transduction to NO is facilitated by a reduction mechanism catalyzed by deoxygenated hemoglobin (deoxy-Hb). In this work, we provide a detailed microscopic study of deoxy-Hb ni...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | , , , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2008
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 15592caa a22013937a 4500 | ||
|---|---|---|---|
| 001 | PAPER-5710 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203522.0 | ||
| 008 | 190411s2008 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-51849127392 | |
| 024 | 7 | |2 cas |a ferric ion, 20074-52-6; heme, 14875-96-8; histidine, 645-35-2, 7006-35-1, 71-00-1; nitric oxide, 10102-43-9; nitrite reductase, 9080-03-9; nitrite, 14797-65-0; nitrogen, 7727-37-9; nitrous acid, 7782-77-6; oxygen, 7782-44-7; Anions; deoxyhemoglobin, 9008-02-0; Hemoglobins; Histidine, 71-00-1; Ligands; Nitric Oxide, 10102-43-9; Nitrite Reductases, EC 1.7.-; Nitrites | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a BICHA | ||
| 100 | 1 | |a Perissinotti, L.L. | |
| 245 | 1 | 2 | |a A microscopic study of the deoxyhemoglobin-catalyzed generation of nitric oxide from nitrite anion |
| 260 | |c 2008 | ||
| 270 | 1 | 0 | |m Estrin, D. A.; Departamento de Quimica Inorganica, Analitica Y Quimica Fisica/INQUIMAE, Facultad de Ciencias Exactas Y Naturales, Pabellón II, C1428EHA Buenos Aires, Argentina; email: dario@qi.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Gladwin, M.T., Schechter, A.N., NO contest - Nitrite versus S-nitroso-hemoglobin (2004) Circ. Res, 94, pp. 851-855 | ||
| 504 | |a Stamler, J.S., Jaraki, O., Osborne, J., Simon, D.I., Keaney, J., Vita, J., Singel, D., Loscalzo, J., Nitric-oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum-albumin (1992) Proc. Natl. Acad. Sci. U.S.A, 89, pp. 7674-7677 | ||
| 504 | |a Stamler, J.S., Jia, L., Eu, J.P., McMahon, T.J., Demchenko, I.T., Bonaventura, J., Gernert, K., Piantadosi, C.A., Blood flow regulation by S-nitrosohemoglobin in the physiological oxygen gradient (1997) Science, 276, pp. 2034-2037 | ||
| 504 | |a Cosby, K., Partovi, K.S., Crawford, J.H., Patel, R.P., Reiter, C.D., Martyr, S., Yang, B.K., Gladwin, M.T., Nitrite reduction to nitric oxide by deoxyhemoglobin vasodilates the human circulation (2003) Nat. Med, 9, pp. 1498-1505 | ||
| 504 | |a Reutov, V.P., Biochemical predetermination of the NO synthase and nitrite reductase components of the nitric oxide cycle (1999) Biochemistry (Moscow), 64, pp. 528-542 | ||
| 504 | |a Reutov, V.P., Sorokina, E.G., NO-synthase and nitrite-reductase components of nitric oxide cycle (1998) Biochemistry (Moscow), 63, pp. 874-884 | ||
| 504 | |a Brooks, C.L., Characterization of "native" apomyoglobin by molecular dynamics simulation (1992) J. Mol. Biol, 227, pp. 375-380 | ||
| 504 | |a Kim-Shapiro, D.B., Gladwin, M.T., Patel, R.P., Hogg, N., The reaction between nitrite and hemoglobin: The role of nitrite in hemoglobin-mediated hypoxic vasodilation (2005) J. Inorg. Biochem, 99, pp. 237-246 | ||
| 504 | |a Doyle, M.P., Pickering, R.A., Deweert, T.M., Hoekstra, J.W., Pater, D., Kinetics and mechanism of the oxidation of human deoxyhemoglobin by nitrites (1981) J. Biol. Chem, 256, pp. 2393-2398 | ||
| 504 | |a Huang, K.T., Keszler, A., Patel, N., Patel, R.P., Patel, R.P., Gladwin, M.T., Kim-Shapiro, D.B., Hogg, N., The reaction between nitrite and deoxyhemoglobin - Reassessment of reaction kinetics and stoichiometry (2005) J. Biol. Chem, 280, pp. 31126-31131 | ||
| 504 | |a Huang, Z., Shiva, S., Kim-Shapiro, D.B., Patel, R.P., Ringwood, L.A., Irby, C.E., Huang, K.T., Gladwin, M.T., Enzymatic function of hemoglobin as a nitrite reductase that produces NO under allosteric control (2005) J. Clin. Invest, 115, pp. 2099-2107 | ||
| 504 | |a Basu, S., Grubina, R., Huang, J., Conradie, J., Huang, Z., Jeffers, A., Jiang, A., Kim-Shapiro, D.B., Catalytic generation of N2O3 by the concerted nitrite reductase and anhydrase activity of hemoglobin (2007) Nat. Chem. Biol, 3, pp. 785-794 | ||
| 504 | |a Williams, P.A., Fulop, V., Garman, E.F., Saunders, N.F.W., Ferguson, S.J., Hajdu, J., Haem-ligand switching during catalysis in crystals of a nitrogen-cycle enzyme (1997) Nature, 389, pp. 406-412 | ||
| 504 | |a George, S.J., Allen, J.W.A., Ferguson, S.J., Thorneley, R.N.F., Time-resolved infrared spectroscopy reveals a stable ferric heme-NO intermediate in the reaction of Paracoccus pantotrophus cytochrome cd(1) nitrite reductase with nitrite (2000) J. Biol. Chem, 275, pp. 33231-33237 | ||
| 504 | |a Marti, M.A., Crespo, A., Bari, S.E., Doctorovich, F.A., Estrin, D.A., QM-MM study of nitrite reduction by nitrite reductase of Pseudomonas aeruginosa (2004) J. Phys. Chem. B, 108, pp. 18073-18080 | ||
| 504 | |a Ranghino, G., Scorza, E., Sjogren, T., Williams, P.A., Ricci, M., Hajdu, J., Quantum mechanical interpretation of nitrite reduction by cytochrome cd(1) nitrite reductase from Paracoccus pantotrophus (2000) Biochemistry, 39, pp. 10958-10966 | ||
| 504 | |a Rinaldo, S., Arcovito, A., Brunori, M., Cutruzzola, F., Fast dissociation of nitric oxide from ferrous Pseudomonas aeruginosa cd1 nitrite reductase - A novel outlook on the catalytic mechanism (2007) J. Biol. Chem, 282, pp. 14761-14767 | ||
| 504 | |a Averill, B.A., Dissimilatory nitrite and nitric oxide reductases (1996) Chem. Rev, 96, pp. 2951-2964 | ||
| 504 | |a Cutruzzola, F., Brown, K., Wilson, E.K., Bellelli, A., Arese, M., Tegoni, M., Cambillau, C., Brunori, M., The nitrite reductase from Pseudomonas aeruginosa: Essential role of two active-site histidines in the catalytic and structural properties (2001) Proc. Natl. Acad. Sci. U.S.A, 98, pp. 2232-2237 | ||
| 504 | |a Wyllie, G.R.A., Scheidt, W.R., Solid-state structures of metalloporphyrin NOx compounds (2002) Chem. Rev, 102, pp. 1067-1089 | ||
| 504 | |a Copeland, D.M., Soares, A.S., West, A.H., Richter-Addo, G.B., Crystal structures of the nitrite and nitric oxide complexes of horse heart myoglobin (2006) J. Inorg. Biochem, 100, pp. 1413-1425 | ||
| 504 | |a Silaghi-Dumitrescu, R., Linkage isomerism in nitrite reduction by cytochrome cd(1) nitrite reductase (2004) Inorg. Chem, 43, pp. 3715-3718 | ||
| 504 | |a Lumme, P., Tummavuo, J., Potentiometric determination of ionization constant of nitrous acid in aqueous sodium perchlorate solutions at 25 degrees C (1965) Acta Chem. Scand, 19, p. 617 | ||
| 504 | |a Seixas, F.A.V., De Azevedo Jr., W.F., Colombo, M.F., Crystallization and X-ray diffraction data analysis of human deoxyhaemoglobin A(o) fully stripped of any anions (1999) Acta Crystallogr., Sect D: Biol. Crystallogr, 55, pp. 1914-1916 | ||
| 504 | |a Jorgensen, W.L., Chandrasekhar, J., Madura, J.D., Impey, R.W., Klein, M.L., Comparison of simple potential functions for simulating liquid water (1983) J. Chem. Phys, 79, pp. 926-935 | ||
| 504 | |a Ryckaert, J.P., Ciccotti, G., Berendsen, H.J.C., Numerical integration of the cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes (1977) J. Comput. Phys, 23, pp. 327-341 | ||
| 504 | |a Bayly, C.I., Cieplak, P., Cornell, W.D., Kollman, P.A., A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model (1993) J. Phys. Chem, 97, pp. 10269-10280 | ||
| 504 | |a Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Jr, Stratmann, R, Burant, J, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Baboul, A. G, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B, Chen, W, Wong, M. W, Andres, J. L, Gonzalez, C, Head-Gordon, M, Replogle, E. S, and Pople, J. A, 1998 Gaussian 98 Rev. A7, Gaussian, Inc, Pittsburgh, PA; Wang, J.M., Cieplak, P., Kollman, P.A., How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? (2000) J. Comput. Chem, 21, pp. 1049-1074 | ||
| 504 | |a Scherlis, D.A., Estrin, D.A., Hydrogen bonding and O-2 affinity of hemoglobins (2001) J. Am. Chem. Soc, 123, pp. 8436-8437 | ||
| 504 | |a Scherlis, D.A., Marti, M.A., Ordejon, P., Estrin, D.A., Environment effects on chemical reactivity of heme proteins (2002) Int. J. Quantum Chem, 90, pp. 1505-1514 | ||
| 504 | |a Scheidt, W.R., Reed, C.A., Spin-state/stereochemical relationships in iron porphyrins: Implications for the hemoproteins (1981) Chem. Rev, 81, pp. 543-555 | ||
| 504 | |a Soler, J.M., Artacho, E., Gale, J.D., Garcia, A., Junquera, J., Ordejon, P., Sanchez-Portal, D., The SIESTA method for ab initio order-N materials simulation (2002) J. Phys.: Condens. Matter, 14, pp. 2745-2779 | ||
| 504 | |a Marti, M.A., Crespo, A., Capece, L., Boechi, L., Bikiel, D.E., Scherlis, D.A., Estrin, D.A., Dioxygen affinity in heme proteins investigated by computer simulation (2006) J. Inorg. Biochem, 100, pp. 761-770 | ||
| 504 | |a Perdew, J.P., Burke, K., Ernzerhof, M., Generalized gradient approximation made simple (1996) Phys. Rev. Lett, 77, pp. 3865-3868 | ||
| 504 | |a Perdew, J.P., Burke, K., Ernzerhof, M., Local and gradient-corrected density functionals (1996) ACS Symp. Ser, 629, pp. 453-462 | ||
| 504 | |a Marti, M.A., Scherlis, D.A., Doctorovich, F.A., Ordejon, P., Estrin, D.A., Modulation of the NO trans effect in heme proteins: Implications for the activation of soluble guanylate cyclase (2003) J. Biol. Inorg. Chem, 8, pp. 595-600 | ||
| 504 | |a Eichinger, M., Tavan, P., Hutter, J., Parrinello, M., A hybrid method for solutes in complex solvents: Density functional theory combined with empirical force fields (1999) J. Chem. Phys, 110, pp. 10452-10467 | ||
| 504 | |a Rovira, C., Schulze, B., Eichinger, M., Evanseck, J.D., Parrinello, M., Influence of the heme pocket conformation on the structure and vibrations of the Fe-CO bond in myoglobin: A QM/MM density functional study (2001) Biophys. J, 81, pp. 435-445 | ||
| 504 | |a Novozhilova, I.V., Coppens, P., Lee, J., Richter-Addo, G.B., Bagley, K.A., Experimental and density functional theoretical investigations of linkage isomerism in six-coordinate {FeNO}6 iron porphyrins with axial nitrosyl and nitro ligands (2006) J. Am. Chem. Soc, 128, pp. 2093-2104 | ||
| 504 | |a Enemark, J.H., Feltham, R.D., Principles of structure, bonding, and reactivity for metal nitrosyl complexes (1974) Coord. Chem. Rev, 13, pp. 339-406 | ||
| 504 | |a Wasser, I.M., De Vries, S., Moenne-Loccoz, P., Schroder, I., Karlin, K.D., Nitric oxide in biological denitrification: Fe/Cu metalloenzyme and metal complex NOx redox chemistry (2002) Chem. Rev, 102, pp. 1201-1234 | ||
| 504 | |a Laverman, L.E., Wanat, A., Oszajca, J., Stochel, G., Ford, P.C., van Eldik, R., Mechanistic studies on the reversible binding of nitric oxide to metmyoglobin (2001) J. Am. Chem. Soc, 123, pp. 285-293 | ||
| 504 | |a Luchsinger, B.P., Rich, E.N., Yan, Y., Williams, E.M., Stamler, J.S., Singel, D.J., Assessments of the chemistry and vasodilatory activity of nitrite with hemoglobin under physiologically relevant conditions (2005) J. Inorg. Biochem, 99, pp. 912-921 | ||
| 504 | |a Coppens, P., Novozhilova, I., Kovalevsky, A., Photo-induced linkage isomers of transition-metal nitrosyl compounds and related complexes (2002) Chem. Rev, 102, pp. 861-884 | ||
| 504 | |a Kujime, M., Fujii, H., Spectroscopic characterization of reaction intermediates in a model for copper nitrite reductase (2006) Angew. Chem., Int. Ed, 45, pp. 1089-1092 | ||
| 504 | |a Suruga, K., Murakami, K., Taniyama, Y., Hama, T., Chida, H., Satoh, T., Yamada, S., Oku, T., A novel microperoxidase activity: Methyl viologen-linked nitrite reducing activity of microperoxidase (2004) Biochem. Biophys. Res. Commun, 315, pp. 815-822 | ||
| 520 | 3 | |a There is recent evidence suggesting that nitrite anion (NO2 -) represents the major intravascular NO storage molecule whose transduction to NO is facilitated by a reduction mechanism catalyzed by deoxygenated hemoglobin (deoxy-Hb). In this work, we provide a detailed microscopic study of deoxy-Hb nitrite reductase (NIR) activity by combining classical molecular dynamics and hybrid quantum mechanical-molecular mechanical simulations. Our results point out that two alternative mechanisms could be operative and suggest that the most energetic barriers should stem from either reprotonation of the distal histidine or NO dissociation from the ferric heme. In the first proposed mechanism, which is similar to that proposed for bacterial NIRs, nitrite anion or nitrous acid coordinates to the heme through the N atom. This pathway involves HisE7 in a one or two proton transfer process, depending on whether the active species is nitrite anion or nitrous acid, to yield an intermediate Fe(III)NO species which eventually dissociates leading to NO and methemoglobin. In the second mechanism, the nitrite anion coordinates to the heme through the O atom. This pathway requires only one proton transfer from HisE7 and leads directly to the formation of a hydroxo Fe(III) complex and NO. © 2008 American Chemical Society. |l eng | |
| 593 | |a Departamento de Quimica Inorganica, Analitica Y Quimica Fisica/INQUIMAE, Facultad de Ciencias Exactas Y Naturales, Pabellón II, C1428EHA Buenos Aires, Argentina | ||
| 593 | |a Departament de Fisicoquímica, Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, 08028 Barcelona, Spain | ||
| 690 | 1 | 0 | |a NITRIC OXIDE |
| 690 | 1 | 0 | |a DEOXY HEMOGLOBIN |
| 690 | 1 | 0 | |a MICROSCOPIC STUDY |
| 690 | 1 | 0 | |a NITRIC OXIDES |
| 690 | 1 | 0 | |a NITRITE ANION |
| 690 | 1 | 0 | |a NEGATIVE IONS |
| 690 | 1 | 0 | |a DEOXYHEMOGLOBIN |
| 690 | 1 | 0 | |a FERRIC ION |
| 690 | 1 | 0 | |a HEME |
| 690 | 1 | 0 | |a HISTIDINE |
| 690 | 1 | 0 | |a METHEMOGLOBIN |
| 690 | 1 | 0 | |a NITRIC OXIDE |
| 690 | 1 | 0 | |a NITRITE |
| 690 | 1 | 0 | |a NITRITE REDUCTASE |
| 690 | 1 | 0 | |a NITROGEN |
| 690 | 1 | 0 | |a NITROUS ACID |
| 690 | 1 | 0 | |a OXYGEN |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a COMPLEX FORMATION |
| 690 | 1 | 0 | |a ENZYME ACTIVITY |
| 690 | 1 | 0 | |a HUMAN |
| 690 | 1 | 0 | |a MOLECULAR DYNAMICS |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a PROTON TRANSPORT |
| 690 | 1 | 0 | |a QUANTUM MECHANICS |
| 690 | 1 | 0 | |a ANIONS |
| 690 | 1 | 0 | |a BINDING SITES |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a HEMOGLOBINS |
| 690 | 1 | 0 | |a HISTIDINE |
| 690 | 1 | 0 | |a HUMANS |
| 690 | 1 | 0 | |a LIGANDS |
| 690 | 1 | 0 | |a MODELS, MOLECULAR |
| 690 | 1 | 0 | |a NITRIC OXIDE |
| 690 | 1 | 0 | |a NITRITE REDUCTASES |
| 690 | 1 | 0 | |a NITRITES |
| 690 | 1 | 0 | |a PROTEIN CONFORMATION |
| 690 | 1 | 0 | |a BACTERIA (MICROORGANISMS) |
| 700 | 1 | |a Marti, M.A. | |
| 700 | 1 | |a Doctorovich, F. | |
| 700 | 1 | |a Luque, F.J. | |
| 700 | 1 | |a Estrin, D.A. | |
| 773 | 0 | |d 2008 |g v. 47 |h pp. 9793-9802 |k n. 37 |p Biochemistry |x 00062960 |w (AR-BaUEN)CENRE-755 |t Biochemistry | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-51849127392&doi=10.1021%2fbi801104c&partnerID=40&md5=3f1d1af64c3850299a4a4e726a819deb |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1021/bi801104c |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00062960_v47_n37_p9793_Perissinotti |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00062960_v47_n37_p9793_Perissinotti |y Registro en la Biblioteca Digital |
| 961 | |a paper_00062960_v47_n37_p9793_Perissinotti |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 66663 | ||