Copper(II) Trimethylacetate Complex with Caffeine: Synthesis, Structure, and Biological Activity
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cated to V.V. Minin on the occasion of his 80th birthday
Copper(II) Trimethylacetate Complex with Caffeine: Synthesis, Structure, and Biological Activity D. S. Yambulatova, *, S. A. Nikolaevskiia, I. A. Lutsenkoa, M. A. Kiskina, M. A. Shmeleva, O. B. Bekkerb, N. N. Efimovb, E. A. Ugolkovaa, V. V. Minina, A. A. Sidorova, and I. L. Eremenkoa, c aKurnakov
Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, 119991 Russia Vavilov Institute of General Genetics, Russian Academy of Sciences, Moscow, 119991 Russia c Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia *e-mail: [email protected] b
Received June 9, 2020; revised June 15, 2020; accepted June 17, 2020
Abstract—The reaction of copper(II) trimethylacetate, [Cu(Piv)2]n (Piv = C(Me)3COO–), with caffeine (L) (Cu : L = 1 : 1) in anhydrous acetonitrile yielded the binuclear complex [Cu2(Piv)4(L)2] ⋅ 2CH3CN (I). The structure of the complex in the crystal was established by X-ray diffraction (CIF file CCDC no. 2006753), and the electronic structure was studied by ESR. The effect of caffeine coordination to the biogenic complexing agent was established: the in vitro biological activity of the obtained complex towards the non-pathogenic strain Mycolicibacterium smegmatis was eight times higher than that of free caffeine. Keywords: caffeine, ESR, copper(II) complex, carboxylate, biological activity DOI: 10.1134/S1070328420110093
INTRODUCTION Copper is one of the most important minor nutrients in the human body; it is involved in oxygen transfer and storage processes and in the regulation of oxidation processes in proteins [1]. Copper ions form complexes with various ligands and interact with biomolecules, mainly proteins and nucleic acids [2]. Copper complexes are active against various cancer cells [3–5] and suppress multiplication of some bacteria: salmonellas [6] and E. coli [7, 8]. A trend of modern bioinorganic chemistry is using simple biologically active molecules such as purine bases (theobromine, theophyllin, and caffeine) as ligands [9]. Caffeine is known to be a medicinal agent [10] and to perform a significant role in human life [11]. The platinum compound [P(C6H5)3(CH3)][PtCl3(L)], exhibiting antitumor activity in vivo, can be regarded as one of the first biologically active complexes involving caffeine, that is, 1,3,7-trimethyl-1Hpurine-2,6(3H,7H)-dione (L) [12]. Recently it was shown that free caffeine has a slight cytotoxicity, while gold(I) complexes with L show high and selective cytotoxicities against various types of cancer cells [13]. Moreover, in vitro cyto- and genotoxicities were found for simple zinc complexes [ZnL(H2O)(Hal)2] (Hal =
Cl, Br, I) and for cadmium complexes {[Cd(H2O)2I2] ⋅ L ⋅ 2H2O}n [14, 15]. Carboxylate anions are convenient ligands, which, together with donor molecules, can control the formation of particular molecular or even polymeric metal cores of complexes [16–20]. In addition, depending on the nature of substituents in the carboxylate anions and on
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