Mechanism of cysteine oxidation by peroxynitrite: An integrated experimental and theoretical study

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Since peroxynitrite was identified as a pathophysiological agent it has been implicated in a great variety of cellular processes. Particularly, peroxynitrite mediated oxidation of cellular thiol-containing compounds such as Cys residues, is a key event which has been extensively studied. Although gr...

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Autor principal: Zeida, A.
Otros Autores: González Lebrero, M.C, Radi, R., Trujillo, M., Estrin, D.A
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2013
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PH
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 cas  |a cysteine, 4371-52-2, 52-89-1, 52-90-4; nitrite, 14797-65-0; oxygen, 7782-44-7; peroxynitrous acid, 14691-52-2; Cysteine, K848JZ4886; Fluorides, Q80VPU408O; Peroxynitrous Acid, 14691-52-2; Polyethylenes; Resins, Synthetic; Thermelect 
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100 1 |a Zeida, A. 
245 1 0 |a Mechanism of cysteine oxidation by peroxynitrite: An integrated experimental and theoretical study 
260 |c 2013 
270 1 0 |m Trujillo, M.; Departamento de Bioquímica, Center for Free Radical and Biomedical Research, Universidad de la República, Montevideo, Uruguay; email: madiat@fmed.edu.uy 
506 |2 openaire  |e Política editorial 
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520 3 |a Since peroxynitrite was identified as a pathophysiological agent it has been implicated in a great variety of cellular processes. Particularly, peroxynitrite mediated oxidation of cellular thiol-containing compounds such as Cys residues, is a key event which has been extensively studied. Although great advances have been accomplished, the reaction is not completely understood at the atomic level. Aiming to shed light on this subject, we present an integrated kinetic and theoretical study of the oxidation of free Cys by peroxynitrite. We determined pH-independent thermodynamic activation parameters, namely those corresponding to the reaction between the reactive species: Cys thiolate and peroxynitrous acid. We found a pH-independent activation energy of 8.2 ± 0.6 kcal/mol. Simulations were performed using state of the art hybrid quantum-classical (QM-MM) molecular dynamics simulations. Our results are consistent with a SN2 mechanism, with Cys sulfenic acid and nitrite anion as products. The activation barrier is mostly due to the alignment of sulfur's thiolate atom with the oxygen atoms of the peroxide, along with the concomitant charge reorganization and important changes in the solvation profile. This work provides an atomic detailed description of the reaction mechanism and a framework to understand the environment effects on peroxynitrite reactivity with protein thiols. © 2013 Elsevier Inc. All rights reserved.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: Universidad de la República Uruguay 
536 |a Detalles de la financiación: Agencia Nacional de Investigación e Innovación 
536 |a Detalles de la financiación: Comisión de Investigaciones Científicas 
536 |a Detalles de la financiación: National Institutes of Health, RO1 AI095173 
536 |a Detalles de la financiación: MT 
536 |a Detalles de la financiación: Agencia Nacional de Investigación e Innovación, FCE_2011_1_5706 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: This work was partially supported by the University of Buenos Aires, CONICET and Centro de Biología Estructural Mercosur (CEBEM). The calculations have been performed in FCEN CECAR and MINCyT Cristina computer centers. MT and RR acknowledge the financial support of the Agencia Nacional de Investigación e Innovación (FCE_2011_1_5706, ANII, Uruguay), Comisión Sectorial de Investigación Científica (CSIC), Universidad de la República and the National Institutes of Health (RO1 AI095173). Appendix A 
593 |a Departamento de Química Inorgánica, Analítica y Química-Física, INQUIMAE-CONICET, Universidad de Buenos Aires, Buenos Aires, Argentina 
593 |a IQUIFIB-Dpto. Química Biológica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Buenos Aires, Argentina 
593 |a Departamento de Bioquímica, Center for Free Radical and Biomedical Research, Universidad de la República, Montevideo, Uruguay 
690 1 0 |a CYSTEINE 
690 1 0 |a OXIDATION 
690 1 0 |a PEROXYNITRITE 
690 1 0 |a REDOX HOMEOSTASIS 
690 1 0 |a SN2 
690 1 0 |a THIOLS 
690 1 0 |a CYSTEINE 
690 1 0 |a NITRITE 
690 1 0 |a OXYGEN 
690 1 0 |a PEROXYNITRITE 
690 1 0 |a PEROXYNITROUS ACID 
690 1 0 |a ARTICLE 
690 1 0 |a ATOM 
690 1 0 |a EXPERIMENTAL STUDY 
690 1 0 |a MOLECULAR DYNAMICS 
690 1 0 |a OXIDATION 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a QUANTUM MECHANICS 
690 1 0 |a REACTION ANALYSIS 
690 1 0 |a THEORETICAL STUDY 
690 1 0 |a CYSTEINE 
690 1 0 |a OXIDATION 
690 1 0 |a PEROXYNITRITE 
690 1 0 |a REDOX HOMEOSTASIS 
690 1 0 |a S(N)2 
690 1 0 |a THIOLS 
690 1 0 |a CYSTEINE 
690 1 0 |a FLUORIDES 
690 1 0 |a KINETICS 
690 1 0 |a MOLECULAR CONFORMATION 
690 1 0 |a MOLECULAR DYNAMICS SIMULATION 
690 1 0 |a OXIDATION-REDUCTION 
690 1 0 |a PEROXYNITROUS ACID 
690 1 0 |a POLYETHYLENES 
690 1 0 |a QUANTUM THEORY 
690 1 0 |a RESINS, SYNTHETIC 
650 1 7 |2 spines  |a PH 
700 1 |a González Lebrero, M.C. 
700 1 |a Radi, R. 
700 1 |a Trujillo, M. 
700 1 |a Estrin, D.A. 
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