Study of metal complexation of cardenolides with divalent metal ions by Electrospray Ionization Mass Spectrometry

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Cardenolides are natural products with positive inotropic and cytotoxic activity that are able to interact with metals, although the possible role that these interactions may play in their biological activity is not known. Mixtures of the following cardenolides: digoxigenin (DgG), gitoxigenin (GxG),...

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Autor principal: Siless, G.E
Otros Autores: Butler, M., Cabrera, G.M
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Elsevier B.V. 2017
Acceso en línea:Registro en Scopus
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100 1 |a Siless, G.E. 
245 1 0 |a Study of metal complexation of cardenolides with divalent metal ions by Electrospray Ionization Mass Spectrometry 
260 |b Elsevier B.V.  |c 2017 
270 1 0 |m Cabrera, G.M.; Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón II, 3° piso, Argentina; email: gabyc@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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520 3 |a Cardenolides are natural products with positive inotropic and cytotoxic activity that are able to interact with metals, although the possible role that these interactions may play in their biological activity is not known. Mixtures of the following cardenolides: digoxigenin (DgG), gitoxigenin (GxG), digitoxigenin (DxG), uzarigenin (UzG) and a butenolide, 2(5H)-furanone (Fur), with different metal cations, namely Ca2+, Mg2+, Cu2+, Co2+ and Zn2+,were studied by Electrospray Ionization Mass Spectrometry in a Quadrupole-Time of Flight. The relative stability of the most important adducts was studied by threshold collision induced dissociation, E1/2. Computational modeling of the observed complexes with calcium was performed using DFT B3LYP/6-31G+(d,p) level of theory. Complexes of stoichiometry [nM+Me]2+, with n = 4 to 6 ligands and Me a metal cation, were observed for all studied compounds. The adducts [4M+Me]2+ corresponded to the most intense peaks in most of the mass spectra and showed the highest E1/2. GxG showed a higher tendency to form complexes with low coordination numbers. Calculations showed that the carbonyl oxygen of the butenolide moiety is the most important site of coordination and allowed the proposal of different binding modes to explain the differences observed in the GxG MS spectra. A direct relationship was observed between experimental and computational data, which allowed to predict the MS behavior of these or similar compounds. The analysis can be extrapolated to other compounds with a furanone ring, and used as an analytical tool to characterize furanone compounds, or for the differentiation of DgG and GxG. © 2017 Elsevier B.V.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: This work was supported by Universidad de Buenos Aires, CONICET, ANPCYT and MinCyT. 
593 |a Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón II, 3° piso, Buenos Aires, C1428EHA, Argentina 
593 |a CONICET-Universidad de Buenos Aires, Unidad de Microanálisis y Métodos Físicos aplicados a la Química Orgánica (UMYMFOR), Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón II, 3° piso, Buenos Aires, C1428EHA, Argentina 
690 1 0 |a 2(5H)-FURANONE 
690 1 0 |a CARDENOLIDES 
690 1 0 |a METAL COMPLEXATION 
700 1 |a Butler, M. 
700 1 |a Cabrera, G.M. 
773 0 |d Elsevier B.V., 2017  |g v. 419  |h pp. 44-51  |p Int. J. Mass Spectrom.  |x 13873806  |w (AR-BaUEN)CENRE-5277  |t International Journal of Mass Spectrometry 
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