Semisynthesis, Characterization and Evaluation of New Adenosine Derivatives as Antiproliferative Agents
1
Institute of Chemistry of Natural Resources, University of Talca, 3460000 Talca, Chile
2
Medical School, University of Talca, 3460000 Talca, Chile
3
Programa de Investigación Asociativa en Cáncer Gástrico (PIA-CG), Universidad de Talca, 3460000 Talca, Chile
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(5), 1111; https://doi.org/10.3390/molecules23051111
Received: 6 April 2018 / Revised: 27 April 2018 / Accepted: 5 May 2018 / Published: 8 May 2018
(This article belongs to the Section Medicinal Chemistry)
We describe the semisynthesis and biological effects of adenosine derivatives, which were anticipated to function as agonists for the A3 receptor. Molecular docking was used to select candidate compounds. Fifteen nucleoside derivatives were obtained through nucleophilic substitutions of the N6-position of the nucleoside precursor 6-chloropurine riboside by amines of different origin. All compounds were purified by column chromatography and further characterized by spectroscopic and spectrometric techniques, showing moderate yield. These molecules were then evaluated for their antiproliferative activity in human gastric cancer cells expressing the A3 receptor. We found that the compounds obtained have antiproliferative activity and that new structural modifications can enhance their biological activity. The ADME (Absorption, Distribution, Metabolism and Excretion) properties of the most active compounds were also evaluated theoretically.
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Keywords:
nucleoside derivatives; adenosine; cancer; antiproliferative activity
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MDPI and ACS Style
Valdés Zurita, F.; Brown Vega, N.; Gutiérrez Cabrera, M. Semisynthesis, Characterization and Evaluation of New Adenosine Derivatives as Antiproliferative Agents. Molecules 2018, 23, 1111.
AMA Style
Valdés Zurita F, Brown Vega N, Gutiérrez Cabrera M. Semisynthesis, Characterization and Evaluation of New Adenosine Derivatives as Antiproliferative Agents. Molecules. 2018; 23(5):1111.
Chicago/Turabian StyleValdés Zurita, Francisco; Brown Vega, Nelson; Gutiérrez Cabrera, Margarita. 2018. "Semisynthesis, Characterization and Evaluation of New Adenosine Derivatives as Antiproliferative Agents" Molecules 23, no. 5: 1111.
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