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J Inorg Biochem. 2006 Nov;100(11):1764-73. Epub 2006 Jul 4.

Synthesis, structure and biological activity of copper(II) complexes with oxolinic acid.

Author information

1
Institute of Physical Chemistry, NCSR Demokritos, 15310 Aghia Paraskevi, Attikis, Greece. gpsomas@chem.demokritos.gr <gpsomas@chem.demokritos.gr>

Abstract

The neutral mononuclear copper complexes with the quinolone antibacterial drug oxolinic acid in the presence or not of a nitrogen donor heterocyclic ligand 1,10-phenanthroline, 2,2'-bipyridine or 2,2'-dipyridylamine have been synthesized and characterized with infrared, UV-visible and electron paramagnetic resonance spectroscopies. The experimental data suggest that oxolinic acid acts as a deprotonated bidentate ligand and is coordinated to the metal ion through the pyridone and one carboxylate oxygen atoms. The crystal structure of (chloro)(1,10-phenanthroline)(oxolinato) copper(II), 2, has been determined with X-ray crystallography. For all complexes a distorted square pyramidal environment around Cu(II) is suggested. The EPR (electron paramagnetic resonance) behavior of 2 in aqueous solutions indicates mixture of dimeric and monomeric species. The investigation of the interaction of the complexes with calf-thymus DNA has been performed with diverse spectroscopic techniques and showed that the complexes are bound to calf-thymus DNA. The antimicrobial activity of the complexes has been tested on three different microorganisms. The complexes show a decreased biological activity in comparison to the free oxolinic acid.

PMID:
16904184
DOI:
10.1016/j.jinorgbio.2006.06.012
[Indexed for MEDLINE]

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