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Full Structural Characterization of Homoleptic Complexes Of molecules Article 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 William Meza-Morales 1 , M. Mirian Estévez-Carmona 2 , Yair Alvarez-Ricardo 1 , Marco A. Obregón-Mendoza 1 , Julia Cassani 3, María Teresa Ramírez-Apan 1, Carolina Escobedo-Martínez 4 , Manuel Soriano-García 1, William F. Reynolds 5 and Raúl G. Enríquez 1,* 1 Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, CDMX CP 07340, México; [email protected] (W.M.-M.); [email protected] (Y.A.-R.); [email protected] (M.A.O.-M.); [email protected] (M.T.R.-A.); [email protected] (M.S.-G.) 2 Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Wilfrido Massieu SN, CDMX CP 07738, México; [email protected] 3 Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana, Unidad Xochimilco, CDMX CP 04960, México; [email protected] 4 Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Guanajuato CP 36050, México; [email protected] 5 Department of Chemistry, University of Toronto, Toronto, ON M5S 1A1, Canada; [email protected] * Correspondence: [email protected]; Tel./Fax: +52-5556224404 Received: 3 April 2019; Accepted: 21 April 2019; Published: 23 April 2019 Abstract: 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 β-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 β-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 (IC = 2.03 0.27, 1.58 0.07, 1.58 0.15 and 1.24 0.10 µM respectively) 50 ± ± ± ± compared with butylated hydroxytoluene (BHT) and α-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. Molecules 2019, 24, 1598; doi:10.3390/molecules24081598 www.mdpi.com/journal/molecules Molecules 2019, 24, 1598 2 of 18 Keywords: homoleptic metal complexes; curcuminoids; crystal structures; antioxidant and cytotoxic activity 1. Introduction Curcumin (1,7-bis(4-hydroxy-3-methoxyphenol)-1,6-heptadiene-3,5-diketone) is the key secondary metabolite present in the yellow rhizome of the perennial herb, Curcuma longa, along with desmethoxycurcumin, and bis-desmethoxycurcumin. It has been widely studied for its multiple medicinal properties, e.g., antimicrobial, antioxidant, antibacterial, and anti-inflammatory, including anticancer activity, Alzheimer and infectious diseases [1–7]. However, the low solubility of curcumin in water, and its rapid metabolism and excretion, are related to a poor bioavailability that limits the scope of its potential benefits in living organisms [1,8–12]. Curcumin and curcuminoids, both natural and synthetic, are examples of β-diketone ligands capable of binding to a variety of metals to produce stable complexes [1,2]. The use of metals of physiological interest in complexation, such as magnesium, zinc, copper, and manganese, serves the purpose of exploring the potential benefits of these metal complexes in medicinal therapies, since the positive biological role of such metals is known to a good extent. For example, magnesium (Mg(II)) is a cofactor in several enzymatic reactions mainly related to energy metabolism and the synthesis of nucleic acids [9,13]. Zinc (Zn(II)) is involved in the regulation of mitochondrial apoptosis in many mammalian cells [14]. Copper (Cu(II)) is an essential micronutrient related to mitochondrial respiration, as well as the response to cellular stress. It is also involved in antioxidant and anti-tumoral defense [10,11,15]. Manganese (Mn(II)) is a trace element present in bone, liver, kidney, and pancreas. Mn(II) helps the body form connective tissue, bones, sex hormones and assists in blood clotting. It also plays a role in fat and carbohydrate metabolism, calcium absorption, and blood sugar regulation. This metal is also necessary for normal brain and nerve function and it is also a component of the antioxidant enzyme superoxide dismutase (SOD), helping to quench free radicals and reduce their damage [16,17]. The molecule curcumin belongs to a class of naturally occurring β-diketones, which can act as good ligand, like its closely related acetylacetone, and also displays the typical keto-enol tautomerism. However, unlike acetylacetone, the central β-diketone functionality is flanked by two large groups –CH=CH-C6H4(OH)(OMe)-3,4 bearing phenolic –OH groups, which are reactive centers that can interfere in the preparation of metal complexes. Thus, it was necessary to protect the hydroxyl substituents and use diacetylcurcumin (or 1,7-bis(3-methoxyl-4-acetoxy1)-pheny-1,6-heptadiene-3,5 diketone (DAC)), which proved to be a suitable ligand [1]. Acetylation turns curcumin into a ligand with its main binding capacities at the β-diketone function. Wang et al. (2014) reported, for the first time, the crystal structure of two homoleptic curcumin metal complexes, using as ligands the O-ethoxy and O-butoxy derivatives, through strong alkaline conditions in their synthetic procedure [10]. In other work, Aliaga-Alcalde et al. [18,19] reported the crystal structures of two homoleptic metal complexes with zinc and copper, where the original aromatic rings of curcumin are replaced by anthracene substituents. The scarcity of homoleptic crystal structures reported until now, however, it has been attributed to the low crystallinity of the curcumin-metal association, making the obtention of suitable single crystals difficult [1,10,18–20]. By using diacetylcurcumin, we circumvented this barrier, while preserving the overall structure of curcumin in its complexes. The copper and manganese complexes of diacetylcurcumin have been reported previously [8,16], however, the X-ray structures have not been reported. In a recent work by Meza-Morales et al. (2019), the synthesis of five homoleptic complexes, with copper was reported using different curcuminoids [21], along with their single crystal structures. In the present work, the complexation was conducted under mild conditions to form the Mg(II), Zn(II), Cu(II) and Mn(II) complexes at the β-diketone region, in absence of a strong base. We report the Molecules 2019, 24, x 3 of 21 Molecules(2019)2019, the, 24 ,synthesis 1598 of five homoleptic complexes, with copper was reported using different3 of 18 curcuminoids [21], along with their single crystal structures. In the present work, the complexation was conducted under mild conditions to form the Mg(II), synthesis (see Scheme1), structural characterization by ultraviolet-visible (UV-Vis), fluorescence, and Zn(II), Cu(II) and Mn(II) complexes at the -diketone region, in absence of a strong base. We report the infraredsynthesis spectroscopy, (see Scheme liquid 1), structural and solid-state characterization Nuclear by Magnetic ultraviolet Resonance,-visible (UV- ElectronicVis), fluorescence, Paramagnetic and Resonance,infrared spectroscopy, magnetic moment liquid and and solid single-crystal-state Nuclear X-ray Magnetic diffraction Resonance, using Electronic diacetylated Paramagnetic curcumin as ligandResonance, with the magnetic physiologically moment and relevant single-crystal metals X-ray Mg, diffraction Zn, Cu using and Mn. diacetylated This approach curcumin successfullyas ligand affordedwith the the physiologically reportedly elusive relevant homoleptic metals Mg, Zn, complexes Cu and Mn. assingle This approach crystals. successfully In addition, afforded these the metal complexesreportedly of elusive DAC showed homoleptic enhanced complexes antioxidant as single crystals and antitumor. In addition activity, these respect metal complexes to the ligand. of DAC showed enhanced antioxidant and antitumor activity respect
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