Conjugation of Ciprofloxacin with Poly(2-oxazoline)s
and Polyethylene Glycol via End Groups
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Abstract
The
antibiotic ciprofloxacin (CIP) was covalently attached to the
chain end of poly(2-methyloxazoline) (PMOx), poly(2-ethyloxazoline)
(PEtOx), and polyethylene glycol (PEG), and the antimicrobial activity
of these conjugates was tested for <i>Staphylococcus aureus</i>, <i>Streptococcus mutans</i>, <i>Escherichia coli</i>, <i>Pseudomonas aeruginosa</i>, and <i>Kleisella
pneumoniae.</i> Chemical structures of the conjugates were proven
by <sup>1</sup>H NMR and electron spray ionization mass spectrometry.
The direct coupling of PMOx and CIP resulted in low antimicrobial
activity. The coupling via a spacer afforded molecular weight dependent
activity with a molar minimal inhibitory concentration that is even
higher than that of the pristine CIP. The antimicrobial activity of
the conjugates increases in the order of PMOx < PEtOx < PEG.
Conjugation of CIP and a quaternary ammonium compound via PMOx did
not result in higher activity, indicating no satellite group or synergistic
effect of the different biocidal end groups