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Molecules 2013, 18(5), 5251-5264; doi:10.3390/molecules18055251
Article

Synthesis and Biological Activity of 6-Selenocaffeine: Potential Modulator of Chemotherapeutic Drugs in Breast Cancer Cells

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Received: 18 March 2013 / Revised: 4 April 2013 / Accepted: 25 April 2013 / Published: 8 May 2013
(This article belongs to the Special Issue Selenium and Tellurium Chemistry)
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Abstract

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.
Keywords: organoselenium compounds; caffeine; modulator of the cytoxicity; oxaliplatin; doxorubicin; cancer therapy organoselenium compounds; caffeine; modulator of the cytoxicity; oxaliplatin; doxorubicin; cancer therapy
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Martins, I.L.; Miranda, J.P.; Oliveira, N.G.; Fernandes, A.S.; Gonçalves, S.; Antunes, A.M.M. Synthesis and Biological Activity of 6-Selenocaffeine: Potential Modulator of Chemotherapeutic Drugs in Breast Cancer Cells. Molecules 2013, 18, 5251-5264.

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