Interactions of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin)

López-Gresa, María Pilar; Ortiz, R.; Perelló, L.; Latorre, Julio; Liu‐González, Malva; Garcı́a-Granda, Santiago; Pérez-Priede, M.; Cantón, Emilia

doi:10.1016/s0162-0134(02)00487-7

Cited by 163 publications

(85 citation statements)

References 27 publications

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“…Metal-organic frameworks were a burgeoning field in the last two decades, not only stems from their tremendous potential applications in areas such as catalysis, molecular adsorption, magnetism, nonlinear optics, and molecular sensing, but also from their novel topologies and intriguing structural diversities [20] [21]. On the other hand, many organic drugs, which possess modified pharmacological and toxicological properties administered in the form of metallic complexes [22], have the potential to act as ligands and the resulting metal-drug complexes are particularly important both in coordination chemistry and biochemistry [23] [24], however, the study of metal-drug complexes is still in its early stages, thus representing a great challenge in current synthetic chemistry and coordination chemistry. Recently, the trend of metal drug complexes has significant interest in order to achieve an enhanced therapeutic effect in combination with decreased toxicity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Some Selenium Nanometric Compounds: Spectroscopic, Biological and Antioxidant Assessments

Atta¹,

El‐Shenawy²,

Koura³

et al. 2014

WJNSE

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Selenium (IV) vitamin A complex as antioxidant drug design was prepared and characterized by microanalysis, conductance, infrared spectra, Raman laser spectra, 1 HNMR spectra, scanning electron microscopy (SEM), X-ray powder diffraction (XRD) and thermogravimetric (TG/DTG and DTA) tool of analyses. Vitamin A chelate was coordinated as a mono-dentate ligand through the oxygen atom of -OH hydroxyl group. Thermal degradation analyses discussed the removal of terminal methyl molecules in the first and second decomposition stage while the organic ligand moieties existed in the third and subsequence steps. The Se (IV) complex in comparable with free vitamin A ligand has been assessed against some kinds of bacteria and fungi which gave a significant inhibition. The surface morphology and nano scale size of selenium metal and its vitamin complex were proved. The activation energy and other thermodynamic parameters (ΔH * , ΔS * and ΔG * ) of Se (IV) complex were calculated using Coats-Redfern and Horowitz-Metzger equations.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Some Selenium Nanometric Compounds: Spectroscopic, Biological and Antioxidant Assessments

Atta¹,

El‐Shenawy²,

Koura³

et al. 2014

WJNSE

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“…This result raises the question whether the ion is already in the protein prior to ligand binding or it is borne by the quinolones. In fact, quinolones are important chelating agents with high affinity for different ions, including Mg 2+ [36,37]. Moreover, the fact that EDTA reverses the action of quinolones can be explained by its sequestering capacity that would limit the number of quinolone-Mg 2+ molecules available in solution, reversing the binding [38].…”

Section: Although Mgmentioning

confidence: 99%

Molecular Determinants of the Bacterial Resistance to Fluoroquinolones: A Computational Study

Lupala¹,

Gómez-Gutiérrez²,

Pérez

2013

CAD

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Quinolones constitute a large class of antibacterial agents whose action is mediated through the formation of a ternary complex with DNA and either, DNA Gyrase or topoisomerase IV, resulting in the inhibition of DNA replication. In order to get a deeper insight into the features of the complex formation, we carried out docking studies of fifteen diverse quinolones to the cleaved topoisomerase IV-DNA complex. Docking studies were performed using the crystal structures of the cleaved complex with levofloxacin and moxifloxacin (pdb entries 3K9F and 2XKK, respectively) using the GOLD software. Ligands dock in positions similar to those of the crystal structures. Analysis of the results reveals that bound quinolones appear intercalated between the two nucleotides that are involved in the DNA cleavage and exhibit hydrogen bonds with Arg 117 and, the latter mediated though a water molecule. Arg 117 has not been described to be involved in resistance, since it is putatively involved in the enzymatic reaction and its mutation would be lethal for the organism. Mutants of Ser 79 exhibit resistance to quinolones which can be explained by the loss of an important anchoring point. Interestingly, quinolone resistance observed in Asp 83 mutants cannot be explained directly on the basis of the loss of a direct interaction, but could be explained on the basis of its involvement at the entrance of the ligands to their binding pocket since the residue is located at the mouth of the pocket. The results of the present study suggest that the 4-keto and 3-carboxyl groups of the fluoroquinolones bind a Mg 2+ before binding to the cleaved topoisomarase IV-DNA complex and use Asp 83 for entry into the binding pocket. Accordingly, mutations that do not conserve the binding capacity for the quinolone-Mg 2+ complex will prevent the binding of this class of ligands. The results we present here are also compared with the structure of PD0305970 a 2,4-dione active against the Ser 79 and Asp 83 mutants.

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“…[67][68][69][70][71][72][73] O efeito do íon metálico na atividade antibacteriana da norfloxacina pode ser ilustrado pelo trabalho de Gao e colaboradores, 73 que mostraram que os complexos de Fe(III) e Zn(II) apresentam atividade superior à da norfloxacina contra E. coli e B. dysenteriae.…”

Section: Coordenação De Metais a Quinolonas E Fluorquinolonasunclassified

Coordenação de metais a antibióticos como uma estratégia de combate à resistência bacteriana

Rocha¹,

Pinto²,

Ruggiero³

et al. 2011

Quím. Nova

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Recebido em 12/1/10; aceito em 2/8/10; publicado na web em 16/11/10 COORDINATION OF METALS TO ANTIBIOTICS AS A STRATEGY TO COMBAT BACTERIAL RESISTANCE. Antibiotic resistance has been growing at an alarming rate and consequently the arsenal of effective antibiotics against Gram-negative and Gram-positive bacteria has dropped dramatically. In this sense there is a strong need to produce new substances that not only have good spectrum of activity, but having new mechanisms of action. In this regard, this paper emphasizes the coordination of metals to antibiotics as a strategy for reversing antibiotic resistance and production of new drugs, with a special focus on quinolones, fluoroquinolones, sulfonamides and tetracyclines.Keywords: antibiotics; metal-based drugs; bacterial resistance. INTRODUÇÃOA descoberta dos antibióticos representa um dos mais importantes marcos da medicina moderna. A introdução das sulfonamidas em 1930 e da penicilina na década posterior provocaram um grande avanço no tratamento de doenças infecciosas, causando uma drásti-ca diminuição nas taxas de mortalidade e uma enorme sensação de bem-estar. 1 O sucesso dos primeiros antibióticos na cura de doenças até então consideradas letais acarretou uma intensa busca por novas drogas. De fato, as décadas de 40, 50 e 60 do século passado foram marcadas pela imensa quantidade de antibióticos produzidos e rapidamente incorporados às práticas clínicas. 2 No entanto, nas décadas posteriores houve um declínio na produção destes compostos. Entre o lançamento das quinolonas em 1962 até a aprovação das oxazolidinonas em 2000, houve pouca inovação no que se refere à introdução de novas classes de antibióticos de uso clínico bem-sucedido. 2 Quando um antibiótico é descoberto e introduzido no mercado, sua utilidade clínica começa a diminuir até um ponto em que há um aumento na restrição de seu uso. Esta restrição é provocada pelo surgimento de cepas resistentes. As bactérias surgiram na terra há bilhões de anos e para sobreviver desenvolveram mecanismos de resistência aos antibióticos que são encontrados livres na natureza. 3 Portanto, não é surpreendente o fato de que muitos antibióticos lançados nas últimas décadas, que são em sua ampla maioria de origem natural ou semissintética, terem utilidade limitada na época de sua descoberta e em pouco tempo se tornarem obsoletos. 3 Outro fator que contribui muito para tornar um antibiótico menos eficiente é a sua utilização indiscriminada e incorreta, o que vem a favorecer o surgimento de micro-organismos resistentes. Atualmente, algumas classes de micro-organismos representam extrema preocupação para a saúde publica. Dentre os que mais provocam mortes no mundo estão o Staphylococcus aureus meticilina-resistente (MRSA), Staphylococcus aureus vancomicina-resistente (VRSA), Escherichia coli, Klebsiella pneumoniae e Pseudomonas aeruginosa, que são bactérias resistentes a múltiplas drogas. Os processos infecciosos causados por estas classes de micro-organismos geralmente estão associados com alta letalidade e altos custos d...

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Interactions of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin)

Cited by 163 publications

References 27 publications

Synthesis and Characterization of Some Selenium Nanometric Compounds: Spectroscopic, Biological and Antioxidant Assessments

Synthesis and Characterization of Some Selenium Nanometric Compounds: Spectroscopic, Biological and Antioxidant Assessments

Molecular Determinants of the Bacterial Resistance to Fluoroquinolones: A Computational Study

Coordenação de metais a antibióticos como uma estratégia de combate à resistência bacteriana

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