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Copper(II)–fluoroquinolone complexes with anti-Trypanosoma cruzi activity and DNA binding ability
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Copper(II)–fluoroquinolone complexes with anti-Trypanosoma cruzi activity and DNA binding ability
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Journal Article
Copper(II)–fluoroquinolone complexes with anti-Trypanosoma cruzi activity and DNA binding ability
2012
Overview
Copper(II) complexes of fluoroquinolone antibacterial agents levofloxacin (LEV) and sparfloxacin (SPAR), containing or not a nitrogen donor heterocyclic ligand, 2,2′-bipyridine (bipy) or 1,10-phenathroline (phen), were prepared and characterized. The complexes are of the type [CuCl
2
(H
2
O)(L)], [CuCl(bipy)(L)]Cl and [CuCl
2
(phen)(L)], where L = LEV or SPAR. The data suggest that LEV and SPAR act as zwitterionic bidentade ligands coordinated to Cu(II) through the carboxylate and ketone oxygen atoms. The electron paramagnetic resonance spectra of the [CuCl(bipy)(L)]Cl and [CuCl
2
(phen)(L)] complexes (L = LEV and SPAR) in aqueous and DMSO solutions indicate mixture of mononuclear and binuclear forms. The Cu(II) complexes, together with the corresponding ligands, were evaluated for their trypanocidal activity in vitro against
Trypanosoma cruzi
, the causative agent of Chagas disease. The assays performed against bloodstream trypomastigotes showed that all complexes were more active than their corresponding ligands. Complexes [CuCl
2
(phen)(LEV)] and [CuCl
2
(phen)(SPAR)] were revealed, among all studied compounds, to be the most active with IC
50
= 1.6 and 4.7 μM, respectively, both presenting a superior effect than benznidazole. The interactions of fluoroquinolones and their Cu(II) complexes with calf-thymus DNA were investigated. These compounds showed binding properties towards DNA, with moderated binding constants values, suggesting that this structure may represent a parasite target.
Publisher
Springer Netherlands,Springer Nature B.V
Subject
/ Antiinfectives and antibacterials
/ Binding
/ Biomedical and Life Sciences
/ Cattle
/ Copper
/ DNA
/ Electron paramagnetic resonance
/ Electron Spin Resonance Spectroscopy
/ Fluoroquinolones - chemistry
/ Fluoroquinolones - metabolism
/ Fluoroquinolones - pharmacology
/ Ligands
/ Organometallic Compounds - chemistry
/ Organometallic Compounds - metabolism
/ Organometallic Compounds - pharmacology
/ Spectra
/ Spectrophotometry, Ultraviolet
/ Trypanocidal Agents - chemistry
/ Trypanocidal Agents - metabolism
/ Trypanocidal Agents - pharmacology
