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The combination of anionic ampicillin with appropriate ammonium, imidazolium, phosphonium, and pyridinium cations yielded active pharmaceutical ingredient ionic liquids (API\u2010ILs) that show potent antiproliferative activities against five different human cancer cell lines: T47D (breast), PC3 (prostate), HepG2 (liver), MG63 (osteosarcoma), and RKO (colon). Some API\u2010ILs showed IC<jats:sub>50<\/jats:sub> values between 5 and 42\u2005n<jats:sc>M<\/jats:sc>, activities that stand in dramatic contrast to the negligible cytotoxic activity level shown by the ampicillin sodium salt. Moreover, very low cytotoxicity against two primary cell lines\u2014skin (SF) and gingival fibroblasts (GF)\u2014indicates that the majority of these API\u2010ILs are nontoxic to normal human cell lines. The most promising combination of antitumor activity and low toxicity toward healthy cells was observed for the 1\u2010hydroxyethyl\u20103\u2010methylimidazolium\u2013ampicillin pair ([C<jats:sub>2<\/jats:sub>OHMIM][Amp]), making this the most suitable lead API\u2010IL for future studies.<\/jats:p>","DOI":"10.1002\/cmdc.201500142","type":"journal-article","created":{"date-parts":[[2015,7,17]],"date-time":"2015-07-17T17:37:02Z","timestamp":1437154622000},"page":"1480-1483","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":77,"title":["Antitumor Activity of Ionic Liquids Based on Ampicillin"],"prefix":"10.1002","volume":"10","author":[{"given":"Ricardo","family":"Ferraz","sequence":"first","affiliation":[]},{"given":"Jo\u00e3o","family":"Costa\u2010Rodrigues","sequence":"additional","affiliation":[]},{"given":"Maria H.","family":"Fernandes","sequence":"additional","affiliation":[]},{"given":"Miguel M.","family":"Santos","sequence":"additional","affiliation":[]},{"given":"Isabel M.","family":"Marrucho","sequence":"additional","affiliation":[]},{"given":"Lu\u00eds Paulo N.","family":"Rebelo","sequence":"additional","affiliation":[]},{"given":"Cristina","family":"Prud\u00eancio","sequence":"additional","affiliation":[]},{"given":"Jo\u00e3o Paulo","family":"Noronha","sequence":"additional","affiliation":[]},{"given":"\u017deljko","family":"Petrovski","sequence":"additional","affiliation":[]},{"given":"Lu\u00eds C.","family":"Branco","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2015,7,16]]},"reference":[{"key":"e_1_2_3_1_2","volume-title":"Ionic Liquids: Applications and Perspectives","year":"2011"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/b706677p"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201100082"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-chembioeng-060713-040024"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2md00269h"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijpharm.2013.08.010"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/bk-2010-1038.ch008"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2009.06.086"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2009.11.085"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11095-009-0030-0"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10646-012-0997-x"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.watres.2013.02.055"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.watres.2009.09.030"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/b617526k"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcb.23295"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/pst.426"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.toxlet.2007.03.008"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/b914284n"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11095-006-9141-z"},{"key":"e_1_2_3_20_2","doi-asserted-by":"crossref","first-page":"1045","DOI":"10.1128\/AEM.64.3.1045-1051.1998","volume":"64","author":"Kiene R. 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