Trapping and characterization of a reaction intermediate in carbapenem hydrolysis by B. cereus metallo-β-lactamase

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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...

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Autor principal: Tioni, M.F
Otros Autores: 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
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2008
Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-56749177280 
024 7 |2 cas  |a carbapenem, 83200-96-8; imipenem, 64221-86-9; beta-Lactamases, EC 3.5.2.6; Carbapenems; Cobalt, 7440-48-4 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a JACSA 
100 1 |a Tioni, M.F. 
245 1 0 |a Trapping and characterization of a reaction intermediate in carbapenem hydrolysis by B. cereus metallo-β-lactamase 
260 |c 2008 
270 1 0 |m Vila, A. J.; Instituto de Biología Molecular Y Celular de Rosario (IBR), Biophysics Section, Universidad Nacional de Rosario, S2002LRK Rosario, Argentina; email: vila@ibrgov.ar 
506 |2 openaire  |e Política editorial 
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520 3 |a 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.  |l eng 
593 |a Instituto de Biología Molecular Y Celular de Rosario (IBR), Biophysics Section, Universidad Nacional de Rosario, S2002LRK Rosario, Argentina 
593 |a Instituto de Química Rosario (IQUIR), Consejo Nacional de Investigaciones Científicas Y Técnicas de Argentina (CONICET), Universidad Nacional de Rosario, Suipacha 531, S2002LRK Rosario, Argentina 
593 |a Departamento de Química Inorgánica, Analítica Y Química Fisica, INQUIMAE-CONICET, Pab. 2, C1428EHA Buenos Aires, Argentina 
593 |a Institut für Chemie, Technische Universität Berlin, Strasse des 17, Juni 135, Sekr. PC14, D10623-Berlin, Germany 
593 |a National Biomedical EPR Center, Department of Biophysics, Medical College of Wisconsin, Milwaukee, WI 53226-0509, United States 
593 |a Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, United States 
593 |a Department of Chemistry, Eastern Illinois University, Charleston, IL 61920, United States 
690 1 0 |a METAL IONS 
690 1 0 |a SUBSTRATES 
690 1 0 |a ANIONIC SPECIES 
690 1 0 |a CARBAPENEMS 
690 1 0 |a CHEMICAL NATURES 
690 1 0 |a DINUCLEAR 
690 1 0 |a LACTAMASE 
690 1 0 |a LACTAMASES 
690 1 0 |a MEROPENEM 
690 1 0 |a RAPID FREEZES 
690 1 0 |a REACTION INTERMEDIATES 
690 1 0 |a RESONANT STRUCTURES 
690 1 0 |a SPECTROSCOPIC FEATURES 
690 1 0 |a ELECTRON SPIN RESONANCE SPECTROSCOPY 
690 1 0 |a CARBAPENEM 
690 1 0 |a CUPRIC ION 
690 1 0 |a IMIPENEM 
690 1 0 |a METAL ION 
690 1 0 |a METALLO BETA LACTAMASE 
690 1 0 |a PENICILLIN DERIVATIVE 
690 1 0 |a ARTICLE 
690 1 0 |a BACILLUS CEREUS 
690 1 0 |a CHEMICAL REACTION 
690 1 0 |a DRUG DESIGN 
690 1 0 |a FREEZING 
690 1 0 |a HYDROLYSIS 
690 1 0 |a NONHUMAN 
690 1 0 |a RAMAN SPECTROMETRY 
690 1 0 |a TURNOVER TIME 
690 1 0 |a BACILLUS CEREUS 
690 1 0 |a BETA-LACTAMASES 
690 1 0 |a CARBAPENEMS 
690 1 0 |a COBALT 
690 1 0 |a ELECTRON SPIN RESONANCE SPECTROSCOPY 
690 1 0 |a HYDROLYSIS 
690 1 0 |a KINETICS 
690 1 0 |a MODELS, BIOLOGICAL 
690 1 0 |a PROTEIN STRUCTURE, TERTIARY 
690 1 0 |a SPECTRUM ANALYSIS, RAMAN 
690 1 0 |a STEREOISOMERISM 
700 1 |a Llarrull, L.I. 
700 1 |a Poeylaut-Palena, A.A. 
700 1 |a Martí, M.A. 
700 1 |a Saggu, M. 
700 1 |a Periyannan, G.R. 
700 1 |a Mata, E.G. 
700 1 |a Bennett, B. 
700 1 |a Murgida, D.H. 
700 1 |a Vila, A.J. 
773 0 |d 2008  |g v. 130  |h pp. 15852-15863  |k n. 47  |p J. Am. Chem. Soc.  |x 00027863  |w (AR-BaUEN)CENRE-19  |t Journal of the American Chemical Society 
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856 4 0 |u https://doi.org/10.1021/ja801169j  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00027863_v130_n47_p15852_Tioni  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v130_n47_p15852_Tioni  |y Registro en la Biblioteca Digital 
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