Adenosine derivates as antioxidant agents: Synthesis, characterization, in vitro activity, and theoretical insights

Francisco Valdes, Nelson Brown, Alejandro Morales-Bayuelo, Luis Prent-Peñaloza, Margarita Gutierrez

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

1 Cita (Scopus)

Resumen

In this work, we present results about the synthesis and the antioxidant properties of seven adenosine derivatives. Four of these compounds were synthesized by substituting the N6-position of adenosine with aliphatic amines, and three were obtained by modification of the ribose ring. All compounds were obtained in pure form using column chromatography, and their structures were elucidated by infrared spectroscopy (IR) and Nuclear Magnetic Resonance (NMR). All adenosine derivatives were further evaluated in vitro as free radical scavengers. Our results show that compounds 1c, 3, and 5 display a potent antioxidant effect compared with the reference compound ascorbic acid. In addition, the absorption, distribution, metabolism and excretion (ADME) calculations show favorable pharmacokinetic parameters for the set of compounds analyzed, which guarantees their suitability as potential antioxidant drugs. Furthermore, theoretical analyses using Molecular Quantum Similarity and reactivity indices were performed in order to discriminate the different reactive sites involved in oxidative processes.

Idioma originalInglés
Número de artículo468
PublicaciónAntioxidants
Volumen8
N.º10
DOI
EstadoPublicada - oct 2019
Publicado de forma externa

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Fisiología
  • Biología molecular
  • Bioquímica clínica
  • Biología celular

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