Artículo

Tioni, M.F.; Llarrull, L.I.; Poeylaut-Palena, A.A.; Martí, M.A.; Saggu, M.; Periyannan, G.R.; Mata, E.G.; Bennett, B.; Murgida, D.H.; Vila, A.J. "Trapping and characterization of a reaction intermediate in carbapenem hydrolysis by B. cereus metallo-β-lactamase" (2008) Journal of the American Chemical Society. 130(47):15852-15863
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Abstract:

Metallo-β-lactamases hydrolyze most β-lactam antibiotics. The lack of a successful inhibitor for them is related to the previous failure to characterize a reaction intermediate with a clinically useful substrate. Stopped-flow experiments together with rapid freeze-quench EPR and Raman spectroscopies were used to characterize the reaction of Co(II)-BcII with imipenem. These studies show that Co(II)-BcII is able to hydrolyze imipenem in both the mono- and dinuclear forms. In contrast to the situation met for penicillin, the species that accumulates during turnover is an enzyme-intermediate adduct in which the β-lactam bond has already been cleaved. This intermediate is a metal-bound anionic species with a novel resonant structure that is stabilized by the metal ion at the DCH or Zn2 site. This species has been characterized based on its spectroscopic features. This represents a novel, previously unforeseen intermediate that is related to the chemical nature of carbapenems, as confirmed by the finding of a similar intermediate for meropenem. Since carbapenems are the only substrates cleaved by B1, B2, and B3 lactamases, identification of this intermediate could be exploited as a first step toward the design of transition-state-based inhibitors for all three classes of metallo-β-lactamases. © 2008 American Chemical Society.

Registro:

Documento: Artículo
Título:Trapping and characterization of a reaction intermediate in carbapenem hydrolysis by B. cereus metallo-β-lactamase
Autor:Tioni, M.F.; Llarrull, L.I.; Poeylaut-Palena, A.A.; Martí, M.A.; Saggu, M.; Periyannan, G.R.; Mata, E.G.; Bennett, B.; Murgida, D.H.; Vila, A.J.
Filiación:Instituto de Biología Molecular Y Celular de Rosario (IBR), Biophysics Section, Universidad Nacional de Rosario, S2002LRK Rosario, Argentina
Instituto de Química Rosario (IQUIR), Consejo Nacional de Investigaciones Científicas Y Técnicas de Argentina (CONICET), Universidad Nacional de Rosario, Suipacha 531, S2002LRK Rosario, Argentina
Departamento de Química Inorgánica, Analítica Y Química Fisica, INQUIMAE-CONICET, Pab. 2, C1428EHA Buenos Aires, Argentina
Institut für Chemie, Technische Universität Berlin, Strasse des 17, Juni 135, Sekr. PC14, D10623-Berlin, Germany
National Biomedical EPR Center, Department of Biophysics, Medical College of Wisconsin, Milwaukee, WI 53226-0509, United States
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, United States
Department of Chemistry, Eastern Illinois University, Charleston, IL 61920, United States
Palabras clave:Metal ions; Substrates; Anionic species; Carbapenems; Chemical natures; Dinuclear; Lactamase; Lactamases; Meropenem; Rapid freezes; Reaction intermediates; Resonant structures; Spectroscopic features; Electron spin resonance spectroscopy; carbapenem; cupric ion; imipenem; metal ion; metallo beta lactamase; penicillin derivative; article; Bacillus cereus; chemical reaction; drug design; freezing; hydrolysis; nonhuman; Raman spectrometry; turnover time; Bacillus cereus; beta-Lactamases; Carbapenems; Cobalt; Electron Spin Resonance Spectroscopy; Hydrolysis; Kinetics; Models, Biological; Protein Structure, Tertiary; Spectrum Analysis, Raman; Stereoisomerism
Año:2008
Volumen:130
Número:47
Página de inicio:15852
Página de fin:15863
DOI: http://dx.doi.org/10.1021/ja801169j
Título revista:Journal of the American Chemical Society
Título revista abreviado:J. Am. Chem. Soc.
ISSN:00027863
CODEN:JACSA
CAS:carbapenem, 83200-96-8; imipenem, 64221-86-9; beta-Lactamases, EC 3.5.2.6; Carbapenems; Cobalt, 7440-48-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v130_n47_p15852_Tioni

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Citas:

---------- APA ----------
Tioni, M.F., Llarrull, L.I., Poeylaut-Palena, A.A., Martí, M.A., Saggu, M., Periyannan, G.R., Mata, E.G.,..., Vila, A.J. (2008) . Trapping and characterization of a reaction intermediate in carbapenem hydrolysis by B. cereus metallo-β-lactamase. Journal of the American Chemical Society, 130(47), 15852-15863.
http://dx.doi.org/10.1021/ja801169j
---------- CHICAGO ----------
Tioni, M.F., Llarrull, L.I., Poeylaut-Palena, A.A., Martí, M.A., Saggu, M., Periyannan, G.R., et al. "Trapping and characterization of a reaction intermediate in carbapenem hydrolysis by B. cereus metallo-β-lactamase" . Journal of the American Chemical Society 130, no. 47 (2008) : 15852-15863.
http://dx.doi.org/10.1021/ja801169j
---------- MLA ----------
Tioni, M.F., Llarrull, L.I., Poeylaut-Palena, A.A., Martí, M.A., Saggu, M., Periyannan, G.R., et al. "Trapping and characterization of a reaction intermediate in carbapenem hydrolysis by B. cereus metallo-β-lactamase" . Journal of the American Chemical Society, vol. 130, no. 47, 2008, pp. 15852-15863.
http://dx.doi.org/10.1021/ja801169j
---------- VANCOUVER ----------
Tioni, M.F., Llarrull, L.I., Poeylaut-Palena, A.A., Martí, M.A., Saggu, M., Periyannan, G.R., et al. Trapping and characterization of a reaction intermediate in carbapenem hydrolysis by B. cereus metallo-β-lactamase. J. Am. Chem. Soc. 2008;130(47):15852-15863.
http://dx.doi.org/10.1021/ja801169j