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Angewandte Chemie International Edition
Vol. 53, No. 15, 2014, Pages: 3830–3834

Antimicrobial Poly(2-methyloxazoline)s with Bioswitchable Activity through Satellite Group Modification

Dipl.-Ing. Christian Krumm, Dipl.-Chem. Simon Harmuth, Montasser Hijazi, Britta Neugebauer, Anne-Larissa Kampmann, Helma Geltenpoth, Prof. Dr. Albert Sickmann and Prof. Dr. Joerg C. Tiller

Biomaterials and Polymer Science, Department of Bio- and Chemical Engineering, TU Dortmund, Emil-Figge-Strasse 66, 44227 Dortmund Germany.


Biocides are widely used for preventing the spread of microbial infections and fouling of materials. Since their use can build up microbial resistance and cause unpredictable long-term environmental problems, new biocidal agents are required. In this study, we demonstrate a concept in which an antimicrobial polymer is deactivated by the cleavage of a single group. Following the satellite group approach, a biocidal quaternary ammonium group was linked through a poly(2-methyloxazoline) to an ester satellite group. The polymer with an octyl-3-propionoate satellite group shows very good antimicrobial activity against Gram-positive bacterial strains. The biocidal polymer was also found to have low hemotoxicity, resulting in a high HC50/MIC value of 120 for S.aureus. Cleaving the ester satellite group resulted in a 30-fold decrease in antimicrobial activity, proving the concept valid. The satellite group could also be cleaved by lipase showing that the antimicrobial activity of the new biocidal polymers is indeed bioswitchable.

Keywords: antimicrobial compounds; biodegradability; biocides; hemotoxicity; polymers.

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