The complexation of transition series metal ions by nalidixic acid and related methoxyquinolones: its influence on partition coefficients with reference to antibacterial activity

Bailey, A. J.; Cole, A.; Goodfield, J.; May, Peter M.; Dreyfuss, M.E.; Midgley, John M.; Williams, David R.

doi:10.1016/0378-5173(84)90028-0

Cited by 14 publications

(1 citation statement)

References 16 publications

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“…Several investigators (19)(20)(21)(22)(23) have studied the changes in the absorption and fluorescence emission properties of the quinolones upon complexation to metal cations such as A13+, Fez+, Ca2+, Mg2+ and Zn2+. These changes have been used to establish the foxmation of complexes between these ions and the 4-keto and 3-carboxy moieties of the quinolone.…”

Section: Introductionmentioning

confidence: 99%

Effect of Magnesium and Calcium Complexation on the Photochemical Properties of Norfloxacin

Martínez

Bilski

Chignell

1996

Photochem & Photobiology

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The fluoroquinolone antibiotics can induce skin photosensitivity in some patients and this has been ascribed to the generation of reactive oxygen species, such as singlet oxygen (OZ[lAg]). We have studied the photochemical properties of the different ionized forms of the fluoroquinolone norfloxacin upon complexation with MgZ+ and Caz+ ions, as it is proposed that the antibiotic exists mainly as a complex in the blood plasma. We found that the norfloxacin cation (pH < 6) shows no photodegradation after UVA irradiation and has a low quantum yield of 02(lAg) generation. The norfloxacin cation does not complex.Ca2+ or Mgz+ ions; when these ions are added to the solution, we observed no changes in the fluorescence quantum yields and singlet oxygen yields (aA). In contrast, the neutral (6 5 pH 4 8.5) and anionic (pH > 9) forms of norfloxacin are able to complex calcium and magnesium, and their generation of Oz ('Ag) is decreased by complexation. The neutral zwitterionic form and the anionic form also quench singlet oxygen by both chemical and physical pathways regardless of complex formation, while physical quenching is observed for the cation. At pH 2 7.4, norfloxacin photobleaches and complexation to Ca2+ and Mgz+ increases the rate at which photobleaching occurs. Thus, both the pH of the medium and complexation with metal cations may affect the phototoxic potential of this antibiotic.

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Section: Introductionmentioning

confidence: 99%

Effect of Magnesium and Calcium Complexation on the Photochemical Properties of Norfloxacin

Martínez

Bilski

Chignell

1996

Photochem & Photobiology

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DNA‐binding, antibacterial and spectral investigations of drug–Fe(II) complexes

Pansuriya

Patel

2007

Applied Organom Chemis

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The antibiotic agent ciprofloxacin is well known for its drug design and coordinating ability towards metal ions. Iron(II) complexes of ciprofloxacin with various neutral bidentate ligands have been prepared. The structure of complexes has been investigated using spectral, physicochemical and elemental analyses. Antibacterial activity has been carried out using agar plate technique against Staphylococcus aureus, Bacillus subtilis, Bacillus cereus, Salmonella typhi, Escherichia coli and Serratia marcescens. The results show a significant increase in antibacterial activity compared with parental ligands, metal salt and standard drugs (ofloxacin, levofloxacin). The DNA binding and cleavage efficacy were determined using absorption titration and gel electrophoresis techniques, respectively. The DNA binding and cleavage efficacy were increased in complexes compared with parental ligands and metal salt.

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Synthesis and structure of the N‐alkyl‐2,6‐dimethyl‐4‐oxopyridine‐3‐carboxylic acids

Dobbin

Hider

Venkatramani

et al. 1993

Journal of Heterocyclic Chem

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A range of N‐alkyl‐2,6‐dimethyl‐4‐oxopyridine‐3‐carboxylic acids XV have been prepared via reactions of primary alkyl amines with differing 2,6‐dimethyl‐4‐oxopyran‐3‐carboxylate esters IX. The quantity of desired product formed and the character of by‐products formed are determined by the natures of the amine and ester IX respectively. X‐ray crystallography data for the N‐ethyl analogue of XV indicates very strong intramolecular hydrogen bonding to be present, with the heterocyclic ring exhibiting considerable aromaticity.

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The complexation of transition series metal ions by nalidixic acid and related methoxyquinolones: its influence on partition coefficients with reference to antibacterial activity

Cited by 14 publications

References 16 publications

Effect of Magnesium and Calcium Complexation on the Photochemical Properties of Norfloxacin

Effect of Magnesium and Calcium Complexation on the Photochemical Properties of Norfloxacin

DNA‐binding, antibacterial and spectral investigations of drug–Fe(II) complexes

Synthesis and structure of the N‐alkyl‐2,6‐dimethyl‐4‐oxopyridine‐3‐carboxylic acids

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