Wydział Chemii

Aleksandra Bykowska

Radosław Starosta

Julia Jezierska

Małgorzata Jeżowska-Bojczuk

2015

RSC Advances

5

80804-80815

10.1039/c5ra07483e

Naukowa

Angielski

Artykuł

In this paper, new copper(I) and copper(II) complexes with phosphine derivatives of two fluoroquinolones (ciprofloxacin and norfloxacin) are presented. The synthesized compounds ([Cu^I-PCp], [Cu^I-PNr], [OPCp-Cu^II]⁺ and [OPNr-Cu^II]⁺) were characterized by elemental analysis and MS as well as by the NMR, EPR and IR spectroscopies. X-ray techniques were used to determine the crystal and molecular structures of [Cu^I-PCp]·CH₂Cl₂·CH₃CN and OPCp-Cu^II]NO₃·3H₂O. For all the studied compounds, the ability to interact with DNA was determined using three different methods. The results of gel electrophoresis revealed that in the presence or absence of H₂O₂, the copper(I) complexes caused only single-stranded cleavage of the sugar–phosphate backbone of DNA. In turn, the copper(II) complexes damaged the plasmid exclusively in the presence of the oxidant. The addition of H₂O₂ caused distinct changes in the plasmid structure, resulting in a complete disappearance of its native form. Forms II and III arising from single- and double-strand cleavage were detected. Studies of the interactions with calf thymus DNA in the presence of ethidium bromide (EB) showed that the tested complexes and phosphines interact with DNA in a partial intercalation mode, contrary to unmodified antibiotic and oxide derivatives, which do not displace EB from the system. Molecular docking (AutoDock Vina program) was performed using the synthetic double-stranded hexadecanucleotide (sequence: ATATCGCGATATCGCG). Data analysis showed that a majority of the compounds preferably bound to the minor or major grooves, however most of them were also able to intercalate with the DNA double helix.

http://dx.doi.org/10.1039/c5ra07483e

https://www.rsc.org/