{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T10:34:35Z","timestamp":1760783675549,"version":"build-2065373602"},"reference-count":42,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2013,5,8]],"date-time":"2013-05-08T00:00:00Z","timestamp":1367971200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>We report the development of a new microwave-based synthetic methodology mediated by Woollins\u2019 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 \u00b5M, 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 \u00b5M) and 6-selenocaffeine (100 \u00b5M) resulted in a slight decrease in cellular viability when compared to doxorubicin (1 \u00b5M) alone. Conversely, the seleno-caffeine derivative at the same concentration markedly increased the viability of oxaliplatin  (100 \u00b5M)-treated cells (p &lt; 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.<\/jats:p>","DOI":"10.3390\/molecules18055251","type":"journal-article","created":{"date-parts":[[2013,5,8]],"date-time":"2013-05-08T11:26:23Z","timestamp":1368012383000},"page":"5251-5264","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Synthesis and Biological Activity of 6-Selenocaffeine: Potential Modulator of Chemotherapeutic Drugs in Breast Cancer Cells"],"prefix":"10.3390","volume":"18","author":[{"given":"In\u00eas","family":"Martins","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade T\u00e9cnica de Lisboa,  1049-001 Lisboa, Portugal"}]},{"given":"Joana","family":"Miranda","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines and Pharmaceutical Sciences (iMed.UL), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"}]},{"given":"Nuno","family":"Oliveira","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines and Pharmaceutical Sciences (iMed.UL), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"}]},{"given":"Ana","family":"Fernandes","sequence":"additional","affiliation":[{"name":"CBIOS, Universidade Lus\u00f3fona de Humanidades e Tecnologias, 1749-024 Lisboa, Portugal"}]},{"given":"Sandrina","family":"Gon\u00e7alves","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines and Pharmaceutical Sciences (iMed.UL), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"}]},{"given":"Alexandra","family":"Antunes","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade T\u00e9cnica de Lisboa,  1049-001 Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2013,5,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"5303","DOI":"10.1021\/jm900852b","article-title":"Discovery of a new template for anticancer agents: 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl-cytosine (2'-F-4'-Seleno-ara-C)","volume":"52","author":"Jeong","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1395","DOI":"10.1016\/j.ejmech.2009.12.039","article-title":"Synthesis of 1-benzyl-3-(5-hydroxymethyl-2-furyl)selenolo[3,2-c]pyrazole derivatives as new anticancer agents","volume":"45","author":"Chou","year":"2010","journal-title":"Eur. J. Med. 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