Conjugation of Ciprofloxacin with Poly(2-oxazoline)s and Polyethylene Glycol via End Groups.
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 Staphylococcus aureus, Streptococcus mutans, Escherichia coli, Pseudomonas aeruginosa, and Kleisella pneumoniae. Chemical structures of the conjugates were proven by (1)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.
Biomaterials and Polymer Science, Department of Bio- and Chemical Engineering, TU Dortmund , Emil-Figge-Straße 66, 44227 Dortmund, Germany.
Martin
M
Schmidt
Biomaterials and Polymer Science, Department of Bio- and Chemical Engineering, TU Dortmund , Emil-Figge-Straße 66, 44227 Dortmund, Germany.
Simon
S
Harmuth
Biomaterials and Polymer Science, Department of Bio- and Chemical Engineering, TU Dortmund , Emil-Figge-Straße 66, 44227 Dortmund, Germany.
Eva Rebecca
ER
Barth
Biomaterials and Polymer Science, Department of Bio- and Chemical Engineering, TU Dortmund , Emil-Figge-Straße 66, 44227 Dortmund, Germany.
Elena
E
Wurm
Leibniz-Institut für Analytische Wissenschaften-ISAS-e.V. , Otto Hahn-Straße 6b, 44227 Dortmund, Germany.
Rita
R
Fobbe
Leibniz-Institut für Analytische Wissenschaften-ISAS-e.V. , Otto Hahn-Straße 6b, 44227 Dortmund, Germany.
Albert
A
Sickmann
Biomaterials and Polymer Science, Department of Bio- and Chemical Engineering, TU Dortmund , Emil-Figge-Straße 66, 44227 Dortmund, Germany.
Christian
C
Krumm
Biomaterials and Polymer Science, Department of Bio- and Chemical Engineering, TU Dortmund , Emil-Figge-Straße 66, 44227 Dortmund, Germany.
Joerg C
JC
Tiller
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D002939:Ciprofloxacin / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D004912:Erythrocytes / Q000187:drug effects; D010080:Oxazoles / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000737:chemistry*; D013552:Swine
D000900:Anti-Bacterial Agents; D010080:Oxazoles; C577913:poly(2-oxazoline); D011092:Polyethylene Glycols; D002939:Ciprofloxacin