Interactions of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin). Spectroscopic and X-ray structural characterization. Antibacterial studies.
Several novel metal-quinolone compounds have been synthesized and characterized by analytical, spectroscopic and X-ray diffraction methods. The crystal structure of the four compounds, Na(2)[(Cd(Cx)3)(Cd(Cx)3(H2O))].12H2O, [Co(Cp)2(H2O)2].9H2O, [Zn(Cp)2(H2O)2].8H2O and [Cd(HCp)2(Cl)2].4H2O, is presented and discussed: HCx=1-ethyl-1,4-dihydro-4-oxo(1,3)-dioxolo(4,5-g)cinnoline-3-carboxylic acid and HCp=1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid. In all these compounds the quinolone acts as a bidentate chelate ligand that binds through one carboxylate oxygen atom and the exocyclic carbonyl oxygen atom. Complexes of ciprofloxacin were screened for their activity against several bacteria, showing activity similar to that of the ligand. In addition, the number of bacteria killed after 3 h of incubation with the ligand, [Co(Cp)2(H2O)2].9H2O, Ni(Cp)2.10H2O and Cu(Cp)2.6H2O, was determined against S. aureus ATCC25923. There is a direct relationship between the growth rate and the lethal rate. Against growing bacteria, the ligand is the most bactericidal and Cu(Cp)2.6H2O is the less bactericidal. On the contrary, against non-dividing bacteria, the complexes were more bactericidal than the ligand, with Cu(Cp)(2).6H(2)O the most bactericidal compound.
López-Gresa
M P
MP
Departamento de Química Inorgánica, Facultad de Farmacia, Universidad de Valencia, Burjassot, Spain.
Ortiz
R
R
Perelló
L
L
Latorre
J
J
Liu-González
M
M
García-Granda
S
S
Pérez-Priede
M
M
Cantón
E
E
D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology; D002937:Cinoxacin / Q000737:chemistry* / Q000494:pharmacology; D002939:Ciprofloxacin / Q000737:chemistry* / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D007477:Ions / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure
D000890:Anti-Infective Agents; D007477:Ions; D008670:Metals; D002939:Ciprofloxacin; D002937:Cinoxacin