Calderón Montaño, José ManuelMadrona, AndrésBurgos Morón, EstefaníaOrta Vázquez, Manuel LuisMateos Cordero, SantiagoEspartero Sánchez, José LuisLópez Lázaro, Miguel2025-01-282025-01-282013-05-02Calderón Montaño, J.M., Madrona, A., Burgos Morón, E., Orta Vázquez, M.L., Mateos Cordero, S., Espartero Sánchez, J.L. y López Lázaro, M. (2013). Selective cytotoxic activity of new lipophilic hydroxytyrosol alkyl ether derivatives. Journal of Agricultural and Food Chemistry, 61 (21), 5046-5053. https://doi.org/10.1021/jf400796p.0021-85611520-5118https://hdl.handle.net/11441/167741Recent data suggest that hydroxytyrosol, a phenolic compound of virgin olive oils, has anticancer activity. This communication reports the synthesis of decyl and hexadecyl hydroxytyrosyl ethers, as well as the cytotoxic activity of hydroxytyrosol and a series of seven hydroxytyrosol alkyl ether derivatives against A549 lung cancer cells and MRC5 non-malignant lung fibroblasts. Hydroxytyrosyl dodecyl ether (HTDE) showed the highest selective cytotoxicity, and possible mechanisms of action were investigated; results suggest that HTDE can moderately inhibit glycolysis, induce oxidative stress, and cause DNA damage in A549 cells. The combination of HTDE with the anticancer drug 5-fluorouracil induced a synergistic cytotoxicity in A549 cancer cells but not in non-malignant MRC5 cells. HTDE also displayed selective cytotoxicity against MCF7 breast cancer cells versus MCF10 normal breast epithelial cells in the 1-30 μM range. These results suggest that the cytotoxicity of HTDE is more potent and selective than that of parent compound hydroxytyrosol.application/pdf32 p.engAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/AnticancerCancerCytotoxicLipophilic derivativesOlive oilPhenolic compoundsinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccesshttps://doi.org/10.1021/jf400796p