Abstract

BERRIO ESCOBAR, Jhon Fernando et al. Synthesis and cytotoxic activity of conjugates of the uridine with triterpenes on breast cancer cells. Ars Pharm [online]. 2016, vol.57, n.2, pp.55-62. ISSN 2340-9894.  https://dx.doi.org/10.30827/ars.v57i2.4962.

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.

Keywords : breast cancer; cytotoxic activity; nucleosides; triterpenes; uridine derivatives.

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