- Abstract
Rhenium complexes with the antibiotic ciprofloxacin have been prepared to be studied as models of technetium radiopharmaceuticals. With this aim, the new rhenium complexes 1 {[ReO(Cpf)2]Cl}, 2 {[ReO(CpfH)2]Cl3} and 3 {fac-[Re(CO)3(H2O)(Cpf)]} with ciprofloxacin (CpfH=ciprofloxacin; Cpf=conjugated base of ciprofloxacin) have been synthesised and characterised by elemental analyses, IR, NMR ((1)H, (19)F and (13)C CP-MAS) spectroscopy, as well as MS measurements. All spectroscopic data are consistent with the coordination of ciprofloxacin in all these complexes through the carbonyl and the carboxylate oxygen atoms with the formation of a six member chelate ring. The study of a Tc-ciprofloxacin solution by ESI-MS reveals the presence of [TcO(Cpf)2](+) cations, which agrees with the hypothesis that complexes 1 and 2 can be seen as model rhenium complexes of this radiopharmaceutical. Antimicrobial and DNA gyrase inhibition studies performed with complexes 2 and 3 have shown a very similar behaviour between complex 2 and the free antibiotic, whereas complex 3 exhibit a lower antimicrobial activity. Based on a joint analysis of the data reported in the literature and the chemical and biological results obtained in this study, a tentative proposal to explain some aspects of the behaviour of Tc-ciprofloxacin radiopharmaceutical has been made.
- Alternate Journal
- Bioorg. Med. Chem.
- Authors
- Lecina, Joan, Suades, Joan, Piera, Carlos, Llagostera, Montserrat, and Cortés, Pilar
- Citation Key
- 163
- COinS Data
- Date Published
- 2014 Jul 01
- DOI
- 10.1016/j.bmc.2014.04.058
- ISSN
- 1464-3391
- Issue
- 13
- Keywords
- Anti-Bacterial Agents, Ciprofloxacin, DNA Gyrase, Dose-Response Relationship, Drug, Enterococcus faecalis, Escherichia coli, Molecular Conformation, Organometallic Compounds, Pseudomonas aeruginosa, Radiopharmaceuticals, Rhenium, Staphylococcus aureus, St
- Pagination
- 3262-9
- Journal
- Bioorg Med Chem
- Volume
- 22
- Year of Publication
- 2014