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Open AccessArticle

Adenosine Derivates as Antioxidant Agents: Synthesis, Characterization, in Vitro Activity, and Theoretical Insights

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Organic Synthesis Laboratory and Biological Activity (LSO-Act-Bio), PhD Sciences Mention Investigation and Development of Bioactive Products, Institute of Chemistry of Natural Resources, Universidad de Talca, Casilla 747, Talca 3460000, Chile
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Center for Medical Research, University of Talca School of Medicine, Talca 3460000, Chile
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Programa de Investigacion Asociativa en Cancer Gastrico (PIA-CG), Universidad de Talca, Talca 3460000, Chile
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Centro de Investigación de Procesos del Tecnológico Comfenalco (CIPTEC), Programa de Ingeniería Industrial, Fundación Universitaria Tecnológico Comfenalco–Cartagena, Cr 44 D N 30A, 91, Cartagena-Bolívar 130001, Colombia
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Organic Synthesis Laboratory and Biological Activity (LSO-Act-Bio), PhD Applied Sciences, Faculty of Engineering and Institute of Chemistry of Natural Resources, Universidad de Talca, Casilla 747, Talca 3460000, Chile
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Author to whom correspondence should be addressed.
Antioxidants 2019, 8(10), 468; https://doi.org/10.3390/antiox8100468
Received: 28 August 2019 / Revised: 25 September 2019 / Accepted: 29 September 2019 / Published: 9 October 2019
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. View Full-Text
Keywords: adenosine derivatives; antioxidant; scavenger; Molecular Quantum Similarity index; chemical reactivity index; density functional theory (DFT) adenosine derivatives; antioxidant; scavenger; Molecular Quantum Similarity index; chemical reactivity index; density functional theory (DFT)
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Valdes, F.; Brown, N.; Morales-Bayuelo, A.; Prent-Peñaloza, L.; Gutierrez, M. Adenosine Derivates as Antioxidant Agents: Synthesis, Characterization, in Vitro Activity, and Theoretical Insights. Antioxidants 2019, 8, 468.

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