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Antimicrobial Poly(2‐methyloxazoline)s with Bioswitchable Activity through Satellite Group Modification
Author(s) -
Krumm Christian,
Harmuth Simon,
Hijazi Montasser,
Neugebauer Britta,
Kampmann AnneLarissa,
Geltenpoth Helma,
Sickmann Albert,
Tiller Joerg C.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201311150
Subject(s) - antimicrobial , biocide , polymer , ammonium , chemistry , microbiology and biotechnology , satellite , combinatorial chemistry , organic chemistry , biology , physics , astronomy
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 HC 50 /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.