Different types of copper complexes with the quinolone antimicrobial drugs ofloxacin and norfloxacin: Structure, DNA- and albumin-binding

Živec, Petra; Perdih, Franc; Turel, Iztok; Giester, Gerald; Psomas, George

doi:10.1016/j.jinorgbio.2012.08.008

Cited by 94 publications

(47 citation statements)

References 98 publications

(135 reference statements)

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“…groovebinding) and at a second step they may intercalate within the DNA base pairs [31]. This behavior may elucidate the findings from the UV spectroscopic studies.…”

Section: Dna Binding Studiesmentioning

confidence: 57%

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Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents

Andreou

Dafnopoulos

Tortopidis

et al. 2016

Journal of Photochemistry and Photobiology B: Biology

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Sulfonyloxyl radicals, readily generated upon UV irradiation of p-pyridine sulfonyl ethanone oxime derivatives, effectively cleave DNA, in a pH independent manner, and under either aerobic or anaerobic conditions. pPyridine sulfonyl ethanone oxime derivatives were synthesized from the reaction of p-pyridine ethanone oxime with the corresponding sulfonyl chlorides in good to excellent yields. All compounds, at a concentration of 100 μM, were irradiated at 312 nm for 15 min, after incubation with supercoiled circular pBluescript KS II DNA and resulted in extended single-and double-strand cleavages. The cleavage ability was found to be concentration dependent, with some derivatives exhibiting activity even at nanomolar levels. Besides that, p-pyridine sulfonyl ethanone oxime derivatives showed good affinity to DNA, as it was observed with UV interaction and viscosity experiments with CT DNA and competitive studies with ethidium bromide. The compounds interact to CT DNA probably by non-classical intercalation (i.e. groove-binding) and at a second step they may intercalate within the DNA base pairs. The fluorescence emission spectra of pre-treated EB-DNA exhibited a significant or moderate quenching. Comparing with the known aryl carbonyloxyl radicals the sulfonyloxyl ones are more powerful, with both aryl and alkyl sulfonyl substituted derivatives to exhibit DNA photo-cleaving ability, in significantly lower concentrations. These properties may serve in the discovery of new leads for "on demand" biotechnological and medical applications.

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“…groovebinding) and at a second step they may intercalate within the DNA base pairs [31]. This behavior may elucidate the findings from the UV spectroscopic studies.…”

Section: Dna Binding Studiesmentioning

confidence: 57%

“…6(C)], respectively. This quenching is due to the ability of the compounds to displace EB from the DNA-EB complex and indirectly reveals that their interaction with CT DNA via an intercalative mode may exist [31].…”

Section: Dna Binding Studiesmentioning

confidence: 99%

Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents

Andreou

Dafnopoulos

Tortopidis

et al. 2016

Journal of Photochemistry and Photobiology B: Biology

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“…The structure of a metal complex of silver with OFL has not been published yet. By association with patterns obtained so far using OFL, in this study, it is possible to obtain a compound with a stoichiometric metal: ligand of 1:2 or 1:1 while ratio of 1:3 is unlikely [13][14][15][16][17][18][19][20][21]27]. In the mass spectrum (m/z 830.9) is highlighted the molecular ion Ag(OFL) 2 + , corresponding to ratio metal:ligand of 1:2 combination, and m/z 362.1 corresponding to the molecular ion of the free OFL.…”

Section: Ms Spectra Analysismentioning

confidence: 73%

“…Due to the specific complexation ability of fluoroquinolones, in the case of OFL several metalic complexes (Mg 2+ , Ca 2+ , Ba 2+ , Ni 2+ , Zn 2+ , Cu 2+ , Co 2+ , Pd 2+ , Pt 2+ , Bi 3+ ) have been studied before in terms of antimicrobial activity (including Helicobacter pylori and Mycobacterium tuberculosis), binding to DNA and to albumins [13][14][15][16][17][18][19][20][21]. At the moment only a few metal complexes with silver of antibacterial quinolones are known: nalidixic acid, pipemidic acid (first generation), pefloxacin, norfloxacin, ciprofloxacin (second generation), moxifloxacin (fourth generation) [5,6,11,[22][23][24].…”

Section: Introductionmentioning

confidence: 99%

A New Silver Complex with Ofloxacin – Preliminary Study

Rusu

Popescu

Imre

et al. 2016

Acta Medica Marisiensis

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Objective: Silver complexes of antibacterial quinolones have the potential advantage of combining the antibacterial activity of silver and fluoroquinolones. The objective of our study was the preparation and the preliminary physico-chemical characterization of a silver complex with ofloxacin. Methods: To achieve our goals several spectroscopic methods (ultraviolet spectrophotometry, mass spectrometry, and Fourier transform infrared spectroscopy) and thermal methods (differential scanning calorimetry and thermogravimetric analysis) were used in order to elucidate the chemical structure of the complex. Results: Using mass spectrometry we established the stoichiometric ratio silver:ofloxacin as 1:2. Experimental data suggest a particular coordination for ofloxacin, as a monodentate ligand, in the formation of a complex with silver, through the nitrogen atom from the methyl-piperazine cycle. IntroductionDue to the excellent chelating properties of quinolone antibacterial several metal complexes of these substances were synthesized and studied for their possible antibacterial and antifungal activities. The silver ion is known for its antibacterial and antifungal properties. Fluoroquinolones are synthetic antibacterial agents, with broad spectrum activity, good oral absorption and bioavailability. The 4-oxo and 3-carboxyl groups of fluoroquinolones offer excellent chelating properties for metal ions. Silver complexes of fluoroquinolone antibacterial have the advantage of combining the antibacterial activity of the silver ion with the one of the fluoroquinolone. There are a large number of studies on the complexation of antibacterial fluoroquinolones with metal ions using different metals [1]. Metal complexes have been synthesized with antimicrobial activity equal to or greater with the corresponding quinolone antibacterial. Research on the fluoroquinolone metal complexes has revealed also other biological effects: antifungal, antiparasitic, anticancer, anti-inflammatory, antioxidant and even insulin mimetic [2][3][4]. In the category of metal complexes with promising therapeutic effects are included those containing silver [5][6][7][8][9][10].Complexation of antibacterial quinolones with silver combines the antibacterial activity of Ag (I) with the one of the quinolone. This complexation presents a particular coordination with the quinolone as the monodentate ligand

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“…It is important to note that the anti-T. cruzi agent Nifurtimox has exhibited a promising antitumor effect on neuroblastoma 32 and that other anti-T. …”

Section: Antiproliferative Activitymentioning

confidence: 99%

Copper(II) Nitroaromatic Schiff Base Complexes: Synthesis, Biological Activity and Their Interaction with DNA and Albumins

Martins¹,

Filho²,

Silva³

et al. 2016

Journal of the Brazilian Chemical Society

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Copper(II) complexes of the Schiff base ligands 2-((5-nitrofuran-2-yl)methyleneamino) phenol (HL1) and 2-(4-nitrobenzylideneamino)phenol (HL2) were prepared and characterized using physicochemical and spectroscopic techniques. In these complexes the Schiff base ligands acted as a bidentate donor bound to Cu 2+ through the oxygen and nitrogen atoms in the deprotonated form. The electron paramagnetic resonance spectra, carried out on [CuCl(L1)(phen)].0.5H 2 O and [CuCl(L2)(phen)].2H 2 O complexes, showed the presence of only mononuclear forms. The Cu 2+ complexes and ligands were evaluated for their in vitro trypanocidal activity. The complex [CuCl(L1)(phen)].0.5H 2 O was more active than the free Schiff base and also presented a superior effect to benznidazole, the reference drug. The antiproliferative activity of the Schiff bases and Cu 2+ complexes were evaluated for their effect on seven tumor cell lines and showed a cytostatic and in some cases a cytotoxic effect. These compounds also presented binding properties to deoxyribonucleic acid (DNA) and moderate ability to quench the intrinsic fluorescence of albumins.

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Different types of copper complexes with the quinolone antimicrobial drugs ofloxacin and norfloxacin: Structure, DNA- and albumin-binding

Cited by 94 publications

References 98 publications

Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents

Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents

A New Silver Complex with Ofloxacin – Preliminary Study

Copper(II) Nitroaromatic Schiff Base Complexes: Synthesis, Biological Activity and Their Interaction with DNA and Albumins

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