{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T22:12:24Z","timestamp":1781734344825,"version":"3.54.5"},"reference-count":57,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2019,4,23]],"date-time":"2019-04-23T00:00:00Z","timestamp":1555977600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["CB252524"],"award-info":[{"award-number":["CB252524"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006087","name":"Direcci\u00f3n General de Asuntos del Personal Acad\u00e9mico, Universidad Nacional Aut\u00f3noma de M\u00e9xico","doi-asserted-by":"publisher","award":["IN208516"],"award-info":[{"award-number":["IN208516"]}],"id":[{"id":"10.13039\/501100006087","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>At the present time, scientists place a great deal of effort worldwide trying to improve the therapeutic potential of metal complexes of curcumin and curcuminoids. Herein, the synthesis of four homoleptic metal complexes with diacetylcurcumin (DAC), using a ligand designed to prevent the interaction of phenolic groups, rendering metal complexes through the \u03b2-diketone functionality, is reported. Due to their physiological relevance, we used bivalent magnesium, zinc, copper, and manganese for complexation with DAC. The resulting products were characterized by ultraviolet-visible (UV-Vis), fluorescence spectroscopy, infrared spectroscopy (IR), liquid and solid-state nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), magnetic moment, mass spectrometry (MS), single crystal, and powder X-ray diffraction (SCXRD and PXRD). Crystallization was achieved in dimethylsulfoxide (DMSO) or N,N-dimethylformamide (DMF) as triclinic systems with space group P-1, showing the metal bound to the \u03b2-diketone function, while the 1H-NMR confirmed the preference of the enolic form of the ligand. Single crystal data demonstrated a 1:2 metal:ligand ratio. The inhibition of lipid peroxidation was evaluated using the thiobarbituric acid reactive substance assay (TBARS). All four metal complexes (Mg, Zn, Cu, and Mn) exhibited good antioxidant effect (IC50 = 2.03 \u00b1 0.27, 1.58 \u00b1 0.07, 1.58 \u00b1 0.15 and 1.24 \u00b1 0.10 \u03bcM respectively) compared with butylated hydroxytoluene (BHT) and \u03b1-tocopherol. The cytotoxic activity in human cancer cell lines against colon adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and lung adenocarcinoma (SKLU-1) was found comparable ((DAC)2Mg), or ca. 2-fold higher ((DAC)2Zn) than cisplatin. The acute toxicity assays indicate class 5 toxicity, according to the Organization for Economic Co-operation and Development (OECD) guidelines at doses of 3 g\/kg for all complexes. No mortality or changes in the behavior of animals in any of the treated groups was observed. A therapeutic potential can be envisaged from the relevant cytotoxic activity upon human cancer cell lines in vitro and the undetected in vivo acute toxicity of these compounds.<\/jats:p>","DOI":"10.3390\/molecules24081598","type":"journal-article","created":{"date-parts":[[2019,4,24]],"date-time":"2019-04-24T03:14:28Z","timestamp":1556075668000},"page":"1598","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Full Structural Characterization of Homoleptic Complexes of Diacetylcurcumin with Mg, Zn, Cu, and Mn: Cisplatin-level Cytotoxicity in Vitro with Minimal Acute Toxicity in Vivo"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2759-4334","authenticated-orcid":false,"given":"William","family":"Meza-Morales","sequence":"first","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, CDMX CP 07340, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9945-8545","authenticated-orcid":false,"given":"M. Mirian","family":"Est\u00e9vez-Carmona","sequence":"additional","affiliation":[{"name":"Escuela Nacional de Ciencias Biol\u00f3gicas, Instituto Polit\u00e9cnico Nacional, Wilfrido Massieu SN, CDMX CP 07738, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7001-3358","authenticated-orcid":false,"given":"Yair","family":"Alvarez-Ricardo","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, CDMX CP 07340, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7932-2958","authenticated-orcid":false,"given":"Marco A.","family":"Obreg\u00f3n-Mendoza","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, CDMX CP 07340, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7309-5990","authenticated-orcid":false,"given":"Julia","family":"Cassani","sequence":"additional","affiliation":[{"name":"Departamento de Sistemas Biol\u00f3gicos, Universidad Aut\u00f3noma Metropolitana, Unidad Xochimilco, CDMX CP 04960, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mar\u00eda Teresa","family":"Ram\u00edrez-Apan","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, CDMX CP 07340, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4932-2345","authenticated-orcid":false,"given":"Carolina","family":"Escobedo-Mart\u00ednez","sequence":"additional","affiliation":[{"name":"Departamento de Farmacia, Divisi\u00f3n de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Guanajuato CP 36050, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manuel","family":"Soriano-Garc\u00eda","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, CDMX CP 07340, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"William F.","family":"Reynolds","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Toronto, Toronto, ON M5S 1A1, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ra\u00fal G.","family":"Enr\u00edquez","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, CDMX CP 07340, M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,4,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4986","DOI":"10.1039\/C5CS00088B","article-title":"Metal complexes of curcumin-synthetic strategies, structures and medicinal applications","volume":"44","author":"Wanninger","year":"2015","journal-title":"Chem. 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