Title
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies
Author
Drielly A. Paixão, Ivana M. Marzano, Edgar H.L. Jaimes, Marcos Pivatto, Débora L. Campos, Fernando R. Pavan, Victor M. Deflon, Pedro Ivo da S. Maia, Ana M. Da Costa Ferreira, Isadora A. Uehara, Marcelo J.B. Silva, Françoise V. Botelho, Elene C. Pereira-Maia, Silvana Guilardi, Wendell Guerra
Year
2017
Journal
Journal of Inorganic Biochemistry
Abstract
Five new copper(II) complexes of the type [Cu(Nsingle bondO)(Nsingle bondN)(ClO4)2], in which Nsingle bondO = 4-fluorophenoxyacetic acid hydrazide (4-FH) or 4-nitrobenzoic hydrazide (4-NH) and Nsingle bondN = 1,10-phenanthroline (phen), 4–4′-dimethoxy-2-2′-bipyridine (dmb) or 2,2-bipyridine (bipy) were synthesized and characterized using various spectroscopic methods. The X-ray structural analysis of one representative compound indicates that the geometry around the copper ion is distorted octahedron, in which the ion is coordinated to hydrazide via the terminal nitrogen and the carbonyl oxygen, and to heterocyclic bases via their two nitrogen atoms. Two perchlorate anions occupy the apical positions, completing the coordination sphere. The cytotoxic activity of compounds was investigated in three tumor cell lines (K562, MDA-MB-231 and MCF-7). Concerning K562 cell line, the complexes with 1,10-phenanthroline exhibit high cytotoxic activity and are more active than carboplatin, free ligands and [Cu(phen)2]2 +. Considering the cytotoxicity results, further investigations for the compounds [Cu(4-FH)(phen)(ClO4)2] I and [Cu(4-NH)(phen)(ClO4)2]∙H2O III were performed. Flow cytometric analysis revealed that these complexes induce apoptotic cell death in MDA-MB-231 cell line and bind to DNA with K values of 4.38 × 104 and 2.62 × 104, respectively. These compounds were also evaluated against wild type Mycobacterium tuberculosis (ATCC 27294) and exhibited antimycobacterial activity, displayed MIC values lower than those of the corresponding free ligands.
Instrument
J-815
Keywords
Circular dichroism, DNA structure, Ligand binding, Biochemistry