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Organometallic rhenium tricarbonyl–enrofloxacin and –levofloxacin complexes: synthesis, albumin-binding, DNA-interaction and cell viability studies

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Abstract

Organometallic rhenium complexes have recently been considered in the development of novel antitumor agents due to their suitable properties. A series of rhenium(I) tricarbonyl complexes was synthesized with the quinolone antimicrobial agents enrofloxacin (Herx) and levofloxacin (Hlfx) and solvent (e.g., methanol), imidazole (im) or pyridine (py) as co-ligands. The complexes were characterized by spectroscopic methods. The interaction of the rhenium complexes with bovine serum albumin was investigated by fluorescence emission spectroscopy and the corresponding binding constants were determined. The binding of the rhenium complexes to calf-thymus DNA was monitored by UV–Vis spectroscopy, viscosity measurements and competitive studies with ethidium bromide. These studies indicated that intercalation is the most possible mode of action and the corresponding DNA-binding constants of the complexes were calculated. The cytotoxicity of the Re-complexes against human K-562 erythroleukemia cells was found to be moderate to high. These preliminary results are promising and warrant the design of new Re-complexes with improved properties in future studies.

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Abbreviations

BSA:

Bovine serum albumin

CT:

Calf-thymus

EB:

Ethidium bromide

erx−1 :

Anion of enrofloxacin

Herx:

Enrofloxacin

Hlfx:

Levofloxacin

im:

Imidazole

K :

BSA-binding constant

K b :

DNA-binding constant

k q :

Quenching constant

K SV :

Stern–Volmer constant

lfx−1 :

Anion of levofloxacin

py:

Pyridine

r :

[Complex]/[DNA] mixing ratios

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Authors and Affiliations

  1. Laboratory of Medicinal Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, 54124, Thessaloníki, Greece

    Chaido-Christina Pagoni, Vasiliki-Styliani Xylouri, Georgia Bompola & Dionysia Papagiannopoulou

  2. Laboratory of Pharmacology, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, 54124, Thessaloníki, Greece

    Vasiliki-Styliani Xylouri, Georgios C. Kaiafas, Evangelos Tsoukas & Lefkothea C. Papadopoulou

  3. Laboratory of Inorganic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, 54124, Thessaloníki, Greece

    Marialena Lazou & George Psomas

Authors
  1. Chaido-Christina Pagoni
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  2. Vasiliki-Styliani Xylouri
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  3. Georgios C. Kaiafas
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  9. Dionysia Papagiannopoulou
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Correspondence to Dionysia Papagiannopoulou.

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775_2019_1666_MOESM1_ESM.pdf

The HPLC chromatograms, the 1H-NMR and the ESI-MS spectra of the synthesized Re-complexes are provided. Furthermore, experimental protocols and additional plots of the albumin- and DNA-binding studies of the tested Re-complexes are provided. (PDF 922 kb)

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Pagoni, CC., Xylouri, VS., Kaiafas, G.C. et al. Organometallic rhenium tricarbonyl–enrofloxacin and –levofloxacin complexes: synthesis, albumin-binding, DNA-interaction and cell viability studies. J Biol Inorg Chem 24, 609–619 (2019). https://doi.org/10.1007/s00775-019-01666-1

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  • DOI: https://doi.org/10.1007/s00775-019-01666-1

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