Woollins’ Reagent

López-García, Marta

doi:10.1055/s-0029-1217802

Cited by 1 publication

(1 citation statement)

References 10 publications

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“…Examples of interconversion of carbonyl into selenocarbonyl moieties are relative scarce in the literature, mostly due to the lack of effective synthetic procedures for this transformation. Nonetheless, among the selenium reagents available for this group interconversion [ 18 ], the Woollins’ reagent (2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide, WR), a selenium analogue of Lawesson’s reagent [ 19 ], presents important advantages, namely its higher stability in air and the availability of an easy method for its preparation [ 20 ]. Thus, the use of this reagent for the conversion of carbonyl groups to selenocarbonyl groups in the synthesis of selenoamides [ 21 ] combined with the success of the microwave-accelerated Lawesson’s reagent-mediated thionation of flavonoids [ 22 , 23 ] motivated us to test caffeine selenation using WR under microwave irradiation.…”

Section: Resultsmentioning

confidence: 99%

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

Martins¹,

Miranda

Oliveira

et al. 2013

Molecules

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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.

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