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Molecules 2016, 21(7), 841;

Synthesis and Evaluation of Ciprofloxacin-Nitroxide Conjugates as Anti-Biofilm Agents

ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Faculty of Science and Engineering, Queensland University of Technology, Queensland 4001, Australia
Centre for Microbial Diseases and Immunity Research, Department of Microbiology and Immunology, University of British Columbia, Vancouver, BC V6T 1Z4, Canada
Synthetic Biology Group, MIT Synthetic Biology Center, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Research Laboratory of Electronics, Department of Biological Engineering, Department of Electrical Engineering and Computer Science, Massachusetts Institute of Technology, Cambridge 02139, MA, USA
Broad Institute of MIT and Harvard, Cambridge, MA 02142, USA
Harvard Biophysics Program, Harvard University, Boston, MA 02115, USA
Author to whom correspondence should be addressed.
Academic Editor: Fawaz Aldabbagh
Received: 3 May 2016 / Revised: 17 June 2016 / Accepted: 21 June 2016 / Published: 27 June 2016
(This article belongs to the Special Issue Free Radicals in Organic Synthesis)
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As bacterial biofilms are often refractory to conventional antimicrobials, the need for alternative and/or novel strategies for the treatment of biofilm related infections has become of paramount importance. Herein, we report the synthesis of novel hybrid molecules comprised of two different hindered nitroxides linked to the piperazinyl secondary amine of ciprofloxacin via a tertiary amine linker achieved utilising reductive amination. The corresponding methoxyamine derivatives were prepared alongside their radical-containing counterparts as controls. Subsequent biological evaluation of the hybrid compounds on preformed P. aeruginosa flow cell biofilms divulged significant dispersal and eradication abilities for ciprofloxacin-nitroxide hybrid compound 10 (up to 95% eradication of mature biofilms at 40 μM). Importantly, these hybrids represent the first dual-action antimicrobial-nitroxide agents, which harness the dispersal properties of the nitroxide moiety to circumvent the well-known resistance of biofilms to treatment with antimicrobial agents. View Full-Text
Keywords: radical; antibiotic; biofilm; nitroxide; ciprofloxacin radical; antibiotic; biofilm; nitroxide; ciprofloxacin

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Verderosa, A.D.; Mansour, S.C.; De la Fuente-Núñez, C.; Hancock, R.E.W.; Fairfull-Smith, K.E. Synthesis and Evaluation of Ciprofloxacin-Nitroxide Conjugates as Anti-Biofilm Agents. Molecules 2016, 21, 841.

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