Coordination of the natural ligand lapachol to iron(II): synthesis, theoretical study and antiproliferative activity
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Coordination of the natural ligand lapachol to iron(II): synthesis, theoretical study and antiproliferative activity Tamires D. de Oliveira1,2 · Natália A. Cabeza1,2 · Gelson T. S. T. da Silva3 · Ana L. T. G. Ruiz4 · Anderson R. L. Caires5 · Rafael G. da Silveira6 · Daniela C. M. Rodrigues1 · Antônio R. Fiorucci2 · Ademir dos Anjos1,2 Received: 24 May 2020 / Accepted: 19 September 2020 © Springer Nature Switzerland AG 2020
Abstract Lapachol is a natural naphthoquinone known for having a variety of biological properties, and in recent years, it has been used in the synthesis of metal complexes with biological applications. This work reports on the synthesis, properties and antiproliferative activity of one new metal complex obtained by the reaction of the natural naphthoquinone lapachol with Fe(II). Characterizations by CHN elemental analysis, electrochemical and spectroscopic techniques (infrared, UV–Vis and luminescence) allowed to infer the coordination of two lapachol molecules to the metallic Fe(II) ion through the phenolic and carbonyl oxygens, as well as the presence of two water molecules completing the complex coordination sphere. Molecular modeling was in good agreement with the [Fe(Lap)2(H2O)2]⋅2H2O complex structure proposed from the experimental data. Antiproliferative activity assay revealed the efficiency of the [Fe(Lap)2(H2O)2]⋅2H2O complex against some human tumor cell lines, with lowest TGI (Total growth inhibition) value and higher selectivity index for the glioma tumor cell line (U251).
Introduction In the last decades, research on compounds for cancer treatment been intensified because the number of cancer deaths has been growing considerably year-to-year Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11243-020-00427-3) contains supplementary material, which is available to authorized users. * Tamires D. de Oliveira [email protected] * Ademir dos Anjos [email protected] 1
Centro de Desenvolvimento de Tecnologias Químicas ‑ CDTEQ, Universidade Estadual de Mato Grosso do Sul UEMS, Naviraí, MS, Brazil
2
PGRN, Universidade Estadual do Mato Grosso do Sul - UEMS, Dourados, MS, Brazil
3
Faculdade de Ciências Exatas e da Terra, Universidade Federal da Grande Dourados - UFGD, Dourados, MS, Brazil
4
Faculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas - UNICAMP, Campinas, SP, Brazil
5
Instituto de Física, Universidade Federal de Mato Grosso do Sul - UFMS, Campo Grande, MS, Brazil
6
Instituto Federal Goiano - IFG, Ceres, GO, Brazil
according to The World Health Organization [1]. Although many chemotherapeutic agents are already in use, there still are several obstacles to overcome, such as the resistance and side effect associated with anti-cancer drugs [2]. In this context, natural substances emerge as interesting alternatives for cancer treatment, since they usually exhibit good biological and pharmacological properties. Lapachol (2-hydroxy-3-(3-methyl-2-butenyl)-1, 4-naphthoquinone) is a naphthoquinone
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