Synthesis and Biological Activity of 6-Selenocaffeine: Potential Modulator of C...

• Author(s): Martins, I. L. ; Miranda, J. P. ; Oliveira, N. G. ; Fernandes, A. S. ; Gonçalves, S. ; Antunes, A. M.
• Date: 2013
• Persistent ID: http://hdl.handle.net/10437/5625
• Origin: ReCiL - Repositório Científico Lusófona
• Subject(s): ORGANOSELENIUM COMPOUNDS; CAFFEINE; MODULATOR OF THE CYTOXICITY; OXALIPLATIN; DOXORUBICIN; CANCER THERAPY
• Document Type: Article
• Language: English

Description

We report the development of a new microwave-based synthetic methodology mediated by Woollins’ reagent that allowed an efficient conversion of caffeine into 6-selenocaffeine. A preliminary evaluation on the modulation of antioxidant activity upon selenation of caffeine, using the DPPH assay, indicated a mild antioxidant activity for 6-selenocaffeine, contrasting with caffeine, that exhibited no antioxidant activity under the same experimental conditions. Interestingly, whereas 6-selenocaffeine has revealed to have a low cytotoxic potential in both MCF10A and MCF-7 breast cells (24 h, up to 100 µM, MTT assay), a differential effect was observed when used in combination with the anticancer agents doxorubicin and oxaliplatin in MCF-7 breast cancer cells. The co-treatment of doxorubicin (1 µM) and 6-selenocaffeine (100 µM) resulted in a slight decrease in cellular viability when compared to doxorubicin (1 µM) alone. Conversely, the seleno-caffeine derivative at the same concentration markedly increased the viability of oxaliplatin (100 µM)-treated cells (p < 0.01). Overall, this work highlights an emerging methodology to synthesize organoselenium compounds and points out the differential roles of 6-selenocaffeine in the modulation of the cytotoxicity of anticancer agents.