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Título
A competition between relative stability and binding energy in caffeine phenyl-glucose aggregates: implications in biological mechanisms
Autor
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
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)
Gobierno Vasco - (Grant IT1491-22)
Version del Editor
Propietario de los Derechos
© 2023 The authors
Idioma
eng
Tipo de versión
info:eu-repo/semantics/publishedVersion
Derechos
openAccess
Aparece en las colecciones
Ficheros en el ítem
Tamaño:
1.894Mb
Formato:
Adobe PDF
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