Synthesis and cytotoxic activity of conjugates of the uridine with triterpenes on breast cancer cells

Authors

  • Jhon Fernando Berrío Escobar Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia, Medellín
  • Manuel Humberto Pastrana Restrepo Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia, Medellín
  • Diana Marcela Mejía Cuartas Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia, Medellín
  • Diana Margarita Márquez Fernández Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia, Medellín
  • María Elena Márquez Fernández Universidad Nacional de Colombia, Sede Medellín Colombia
  • Alejandro Martínez Martínez Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia, Medellín

DOI:

https://doi.org/10.30827/ars.v57i2.4962

Keywords:

breast cancer, cytotoxic activity, nucleosides, triterpenes, uridine derivatives

Abstract

Aims: Synthesize of uridine acetonide conjugates with triterpenoids (cholesterol and 3β-5α,8α-endoperoxide-cholest-6-en-3-ol) and succinic acid as linking.

Methods: The acetonide derivative of uridine was prepared with acid catalysis in acetone. Sterols succinates were prepared with succinic anhydride and nucleophilic catalyst 4-N,N-dimethylamino-pyridine (DMAP). The conjugates were synthesized by Steglich method with N,N’-dicyclohexylcarbodiimide (DCC) Coupling agent and DMAP. The compounds were characterized by NMR spectroscopy (1H NMR, 13C NMR), and mass spectrometry. The derivatives were assessed in Chinese Hamster Ovary (CHO) and breast cancer (MCF-7) cell lines.

Results: The conjugates of uridine acetonide with two triterpenes were obtained with yields higher than 80%. The conjugates prepared don’t showed significant inhibition of cell viability on MCF-7 and CHO cell lines, furthermore these substances did not show a relationship dose-response.

Conclusions: The esterification method with coupling agents allowed obtained uridine conjugates with triterpenoids. However the uridine derivatives don’t showed significant cytotoxic activity (p<0,05) against cell lines evaluated.

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Published

2016-06-20

How to Cite

1.
Berrío Escobar JF, Pastrana Restrepo MH, Mejía Cuartas DM, Márquez Fernández DM, Márquez Fernández ME, Martínez Martínez A. Synthesis and cytotoxic activity of conjugates of the uridine with triterpenes on breast cancer cells. Ars Pharm [Internet]. 2016 Jun. 20 [cited 2024 Nov. 28];57(2):55-62. Available from: https://revistaseug.ugr.es/index.php/ars/article/view/4962

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Original Articles