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

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Article number468
JournalAntioxidants
Volume8
Issue number10
DOIs
Publication statusPublished - Oct 2019
Externally publishedYes

Keywords

  • Adenosine derivatives
  • Antioxidant
  • Chemical reactivity index
  • Density functional theory (DFT)
  • Molecular Quantum Similarity index
  • Scavenger

ASJC Scopus subject areas

  • Biochemistry
  • Physiology
  • Molecular Biology
  • Clinical Biochemistry
  • Cell Biology

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