Structure and biological properties of the copper(II) complex with the quinolone antibacterial drug N-propyl-norfloxacin and 2,2'-bipyridine.
The neutral mononuclear copper complex with the quinolone antibacterial drug N-propyl-protected norfloxacin, Hpr-norfloxacin, in the presence of the nitrogen donor heterocyclic ligand 2,2'-bipyridine has been prepared and characterized. The crystal structure of (chloro)(2,2'-bipyridine)(pr-norfloxacinato)copper(II), 1, has been determined and refined with X-ray crystallography. X-band electron paramagnetic resonance (=EPR) spectroscopy at liquid helium temperatures from powdered samples indicates the presence of dimeric units in consistency with the crystal structure. In aqueous solutions of 1 the EPR behavior indicates mixture of dimeric and monomeric species. The antimicrobial activity of the complex has been tested on three different microorganisms and the best inhibition (MIC=0.25mugmL(-1)) has been exhibited against Escherichia coli. The study of the interaction of the complex with calf-thymus DNA has been performed with diverse spectroscopic techniques and has shown that complex 1 is bound to calf-thymus DNA by the intercalative mode. Potential anticancer cytostatic and cytotoxic effects of complex 1 on human promyelocytic leukemia HL-60 and human chronic myelogenous leukemia K562 cell lines have been investigated. Complex 1 shows an increased antiproliferative and necrotic effect on both HL-60 and K562 human leukemia cells in comparison to the free pr-norfloxacin.
Efthimiadou
Eleni K
EK
Institute of Physical Chemistry, NCSR Demokritos, GR-15310 Aghia Paraskevi Attikis, Greece.
Thomadaki
Hellinida
H
Sanakis
Yiannis
Y
Raptopoulou
Catherine P
CP
Katsaros
Nikos
N
Scorilas
Andreas
A
Karaliota
Alexandra
A
Psomas
George
G
D015082:2,2'-Dipyridyl / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D002417:Cattle; D045744:Cell Line, Tumor; D002942:Circular Dichroism; D003300:Copper / Q000737:chemistry*; D004247:DNA / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D004578:Electron Spin Resonance Spectroscopy; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009643:Norfloxacin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000900:Anti-Bacterial Agents; D015082:2,2'-Dipyridyl; D003300:Copper; D004247:DNA; D009643:Norfloxacin