New rhenium complexes with ciprofloxacin as useful models for understanding the properties of [99mTc]-ciprofloxacin radiopharmaceutical
Lecina Vicente, Joan (Universitat Autònoma de Barcelona. Departament de Química)
Cortés Garmendia, M. Pilar (Universitat Autònoma de Barcelona. Departament de Genètica i de Microbiologia)
Llagostera Casas, Montserrat (Universitat Autònoma de Barcelona. Departament de Genètica i de Microbiologia)
Piera, Carlos (Hospital Clínic i Provincial de Barcelona)
Suades Ortuño, Joan (Universitat Autònoma de Barcelona. Departament de Química)

Data:	2014
Resum:	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.
Ajuts:	Ministerio de Economía y Competitividad BIO2012-39682-C02-02 Ministerio de Economía y Competitividad BIO2009-12513-C02-02 Ministerio de Economía y Competitividad CTQ2007-63913 Agència de Gestió d'Ajuts Universitaris i de Recerca 2009/SGR-1106
Drets:	Tots els drets reservats.
Llengua:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Matèria:	Rhenium ; Technetium ; Ciprofloxacin ; Metal carbonyl ; Radiopharmaceutical ; Infection
Publicat a:	Bioorganic & medicinal chemistry, Vol. 22, Issue 13 (July 2014) , p. 3262-3269, ISSN 0968-0896

DOI: 10.1016/j.bmc.2014.04.058
PMID: 24853322

Post-print 36 p, 1.6 MB

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