Interaction of Quinolones with Metal Cations in Aqueous Solution.

Kawai, Yukinori; Matsubayashi, Kyuichi; Hakusui, Hideo

doi:10.1248/cpb.44.1425

Cited by 46 publications

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“…[5][6][7][8][9][10][11][12] On the other hand the Al 3ϩ ion forms the complexes of the highest stability with the ligands containing hard donor groups (i.e. basic negatively charged oxygen atoms).…”

Section: )mentioning

confidence: 99%

“…Thus, the reduced bio-availability of the quinolones in the presence of Al may be explained by chelation between Al 3ϩ ion and the 3-carboxyl and 4-oxo functional groups of the quinolones. [5][6][7][8][9][10][11][12] Besides the reduction of the bioavailability and activity of quinolones the interactions between aluminum ion and quinolones have significant effect on metabolism of aluminum in human organism. Numerous investigations have shown that aluminum can be regarded as detrimental and in particular neurotoxic element.…”

Section: )mentioning

confidence: 99%

“…ca. 2.5 mmol/l the mobilizing power, E is 4ϫ10 6 . Important essential ion is magnesium and it is implicated in quinolone binding to DNA.…”

Section: Esi-ms Measurementsmentioning

confidence: 99%

“…4) To explain the observed phenomenon one may take into account that number of forms in which quinolones may exist in solution (neutral, cationic, zwitterionic and anionic) as well as vicinity of carbonyl and carboxyl groups make them the suitable ligands for hard acid metal ions, in particular for Al 3ϩ . [5][6][7][8][9][10][11][12] On the other hand the Al 3ϩ ion forms the complexes of the highest stability with the ligands containing hard donor groups (i.e. basic negatively charged oxygen atoms).…”

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confidence: 99%

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Solution Equilibria between Aluminum(III) Ion and some Fluoroquinolone Family Members. Spectroscopic and Potentiometric Study

Đjurdjević

Joksović

Jelić

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Fluorinated quinolones are antibacterial agents which chemically, may be regarded as weak substituted heterocyclic amino acids. These drugs primarily find use in the treatment of urinary and respiratory infections. Fluoroquinolones exhibit strong activity against Gram-negative and some Gram-positive bacteria, though many anaerobic strains are resistant.1) Fleroxacin and moxifloxacin are fluoroquinolone family members which belong to 2nd and 4th generation of these drugs, respectively (Chart 1).In clinical practice often, fluoroquinolones are administered concomitantly with other drugs which may contain metal ions. The presence of metal ions from e.g. metal based antacids or multivitamin formulations may significantly affect the activity of quinolones since they can readily bind several divalent or trivalent metal ions.2) Complexation alters solubility, lypophilicity, antimicrobial activity and protein binding of quinolones. The solubility of all ionic quinolone complexes is much greater than that of molecular complexes which are only sparingly soluble.3) Some metal-quinolone complexes show antimicrobial activity comparable to that or free quinolone but in some cases the activity is increased or lowered. Mg 2ϩ and Al 3ϩ were found to decrease the activity of quinolones whereas Fe 3ϩ and Zn 2ϩ complexes exhibit greater activity.2) Clinical investigations have shown that concomitant intake of fluoroquinolones and aluminum-containing antacids results in reduced maximal plasma concentration accompanied by the decrease in AUC. Both effects lead to the decreased bioavailability of the drug, down to 40%. 4)To explain the observed phenomenon one may take into account that number of forms in which quinolones may exist in solution (neutral, cationic, zwitterionic and anionic) as well as vicinity of carbonyl and carboxyl groups make them the suitable ligands for hard acid metal ions, in particular for Al 3ϩ . [5][6][7][8][9][10][11][12] On the other hand the Al 3ϩ ion forms the complexes of the highest stability with the ligands containing hard donor groups (i.e. basic negatively charged oxygen atoms). Thus, the reduced bio-availability of the quinolones in the presence of Al may be explained by chelation between Al 3ϩ ion and the 3-carboxyl and 4-oxo functional groups of the quinolones. [5][6][7][8][9][10][11][12] Besides the reduction of the bioavailability and activity of quinolones the interactions between aluminum ion and quinolones have significant effect on metabolism of aluminum in human organism. Numerous investigations have shown that aluminum can be regarded as detrimental and in particular neurotoxic element.13) Patients with high tissue and serum level of aluminum may develop blood, bone or brain diseases which may be linked to the excess of aluminum.14)The presence of fluoroquinolones may influence Al absorption through the formation of Al-complexes which may be stable enough to produce a sufficient decrease in free Al 3ϩ concentration so that a significant amount of the poorly solu-

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Section: )mentioning

confidence: 99%

Section: )mentioning

confidence: 99%

“…ca. 2.5 mmol/l the mobilizing power, E is 4ϫ10 6 . Important essential ion is magnesium and it is implicated in quinolone binding to DNA.…”

Section: Esi-ms Measurementsmentioning

confidence: 99%

mentioning

confidence: 99%

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Solution Equilibria between Aluminum(III) Ion and some Fluoroquinolone Family Members. Spectroscopic and Potentiometric Study

Đjurdjević

Joksović

Jelić

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Quinolones are potent chelating agents (16,17,20) and there is emerging evidence that they damage juvenile joint cartilage of animals due to their chelating properties, in particular by forming stable chelate complexes with magnesium (24,27). In this respect, it is of interest that lameness and gait alterations closely resembling quinolone-induced arthropathy were described in magnesiumdeficient dogs almost 4 decades ago (26).…”

Section: Integrin Stainingmentioning

confidence: 99%

Immunohistochemistry of Articular Cartilage from Immature Beagle Dogs Dosed with Difloxacin

et al. 1997

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An Electrochemical Immunobiosensor for Direct Detection of Veterinary Drug Residues in Undiluted Complex Matrices

et al. 2011

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An electrochemical immunobiosensor is developed that allows the detection of small molecules, such as drugs, in undiluted complex samples, with no washing or rinsing steps via a displacement assay. This is achieved using an interface comprised of a mixed layer of oligo(phenylethynylene) molecular wire (MW), to allow electrochemical communication, and oligo(ethylene glycol) (OEG) to control the interaction of proteins and electroactive interferences with the electrode surface. The mixed layer is formed from in situ-generated aryl diazonium cations. To the distal end of the MW, a redox probe 1,1'-di(aminomethyl)ferrocene (FDMA) is attached followed by an epitope (the structural feature the antibody selectively recognizes) to which an antibody would bind. Association or dissociation of the antibody with the sensing interface causes a modulation of the ferrocene electrochemistry. Antibody complexed electrodes are exposed to samples containing spiked enrofloxacin (unbound target analyte), in milk and environmental water and interrogated using square wave voltammetry (SWV). The lowest detected concentration of free enrofloxacin was 10 pg mL À1 in phosphate buffer, 50 mM, pH 7. For free enrofloxacin detection in undiluted complex matrices, by adding disodium EDTA (50 mM), the recovery obtained was 94.1 % in skim milk and 88.5 % in stream water, respectively as compared to clean phosphate buffer. The immunobiosensor response time was 10-15 minutes. The sensor performance in milk was shown to be superior to a standard method based on Liquid Chromatography Mass Spectroscopy (LC-MS/MS).

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Interaction of Quinolones with Metal Cations in Aqueous Solution.

Cited by 46 publications

References 0 publications

Solution Equilibria between Aluminum(III) Ion and some Fluoroquinolone Family Members. Spectroscopic and Potentiometric Study

Solution Equilibria between Aluminum(III) Ion and some Fluoroquinolone Family Members. Spectroscopic and Potentiometric Study

Immunohistochemistry of Articular Cartilage from Immature Beagle Dogs Dosed with Difloxacin

An Electrochemical Immunobiosensor for Direct Detection of Veterinary Drug Residues in Undiluted Complex Matrices

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