New rhenium complexes with ciprofloxacin as useful models for understanding the properties of [^99mTc]-ciprofloxacin radiopharmaceutical

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• 作者：Joan Lecina^a ; Pilar Corté ; s^b ; Montserrat Llagostera^b ; Carlos Piera^c ; ^d ; ^&dagger ; ; Joan Suades^a ; ^{Joan.Suades@uab.es" class="auth_mail}
• 关键词：Rhenium ; Technetium ; Ciprofloxacin ; Metal carbonyl ; Radiopharmaceutical ; Infection
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：1 July 2014
• 年：2014
• 卷：22
• 期：13
• 页码：3262-3269
• 全文大小：822 K

文摘

Rhenium complexes with the antibiotic ciprofloxacin have been prepared to be studied as models of technetium radiopharmaceuticals. With this aim, the new rhenium complexes rong class="boldFont">1rong> {[ReO(Cpf)₂]Cl}, rong class="boldFont">2rong> {[ReO(CpfH)₂]Cl₃} and rong class="boldFont">3rong> {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 (¹H, ¹⁹F and ¹³C 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 rong class="boldFont">1rong> and rong class="boldFont">2rong> can be seen as model rhenium complexes of this radiopharmaceutical.

Antimicrobial and DNA gyrase inhibition studies performed with complexes rong class="boldFont">2rong> and rong class="boldFont">3rong> have shown a very similar behaviour between complex rong class="boldFont">2rong> and the free antibiotic, whereas complex rong class="boldFont">3rong> 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.