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.
Highlights
The considerable number of reports of organoselenium compounds presenting antineoplastic effects in recent years has markedly increased the interest in this class of compounds [1,2,3,4,5,6,7,8,9,10]
The results showed that this compound displayed cell viability values similar to untreated control cells revealing no clear cytotoxicity potential to the MCF10A cells under the experimental conditions tested
Selenium has been suggested as a potential agent to be used in cancer prevention, and in cancer treatment, where in combination with anticancer drugs or ionizing radiation, it can improve the efficacy of anticancer therapy [34]. In view of this we aimed to evaluate whether 6-selenocaffeine could be effective on the modulation of the cytotoxic potential of doxorubicin and oxaliplatin in MCF-7 human breast cancer cells
Summary
The considerable number of reports of organoselenium compounds presenting antineoplastic effects in recent years has markedly increased the interest in this class of compounds [1,2,3,4,5,6,7,8,9,10]. Organoselenium compounds are emerging as promising downstream candidates for cancer therapy due to their ability to modulate multiple physiological functions implicated in cancer development, presenting either antioxidant [11,12] anticancer / chemopreventive [13,14] or apoptotic activities [15]. Despite the interest of some of the reported properties a common feature is the usually high concentrations of caffeine required
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