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    Por favor, use este identificador para citar o enlazar este ítem:https://uvadoc.uva.es/handle/10324/69344

    Título
    A competition between relative stability and binding energy in caffeine phenyl-glucose aggregates: implications in biological mechanisms
    Autor
    Calabrese, Camilla
    Camiruaga, Ander
    Parra Santamaria, Maider
    Evangelisti, Luca
    Melandri, Sonia
    Maris, Assimo
    Usabiaga, Imanol
    Fernández, José A.
    Año del Documento
    2023
    Editorial
    MDPI
    Descripción
    Producción Científica
    Documento Fuente
    International Journal of Molecular Sciences, 2023, Vol. 24, Nº. 5, 4390
    Resumen
    Hydrogen bonds and stacking interactions are pivotal in biological mechanisms, although their proper characterisation within a molecular complex remains a difficult task. We used quantum mechanical calculations to characterise the complex between caffeine and phenyl-β-D-glucopyranoside, in which several functional groups of the sugar derivative compete with each other to attract caffeine. Calculations at different levels of theory (M06-2X/6-311++G(d,p) and B3LYP-ED=GD3BJ/def2TZVP) agree to predict several structures similar in stability (relative energy) but with different affinity (binding energy). These computational results were experimentally verified by laser infrared spectroscopy, through which the caffeine·phenyl-β-D-glucopyranoside complex was identified in an isolated environment, produced under supersonic expansion conditions. The experimental observations correlate with the computational results. Caffeine shows intermolecular interaction preferences that combine both hydrogen bonding and stacking interactions. This dual behaviour had already been observed with phenol, and now with phenyl-β-D-glucopyranoside, it is confirmed and maximised. In fact, the size of the complex’s counterparts affects the maximisation of the intermolecular bond strength because of the conformational adaptability given by the stacking interaction. Comparison with the binding of caffeine within the orthosteric site of the A2A adenosine receptor shows that the more strongly bound caffeine·phenyl-β-D-glucopyranoside conformer mimics the interactions occurring within the receptor.
    Materias (normalizadas)
    Caffeine - Physiological effect
    Caffeine
    Sugar
    Azúcar
    Analytical chemistry
    Spectroscopy
    Infrared spectroscopy
    Noncovalent interactions
    Inorganic chemistry
    Organic chemistry
    Molecular biology
    Materias Unesco
    2301 Química Analítica
    2209.21 Espectroscopia
    2301.08 Espectroscopia de Infrarrojos
    2303 Química Inorgánica
    2306 Química Orgánica
    2302.21 Biología Molecular
    ISSN
    1422-0067
    Revisión por pares
    SI
    DOI
    10.3390/ijms24054390
    Patrocinador
    Ministerio de Ciencia, Innovación y Universidades/Agencia Estatal de Investigación (AEI)/10.13039/501100011033 y Fondo Europeo de Desarrollo Regional (FEDER) - (Grants PGC2018-098561)
    Gobierno Vasco - (Grant IT1491-22)
    Version del Editor
    https://www.mdpi.com/1422-0067/24/5/4390
    Propietario de los Derechos
    © 2023 The authors
    Idioma
    eng
    URI
    https://uvadoc.uva.es/handle/10324/69344
    Tipo de versión
    info:eu-repo/semantics/publishedVersion
    Derechos
    openAccess
    Aparece en las colecciones
    • DEP63 - Artículos de revista [324]
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    Nombre:
    A-Competition-between-Relative-Stability-and-Binding-Energy.pdf
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    Universidad de Valladolid

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