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Int. J. Mol. Sci. 2018, 19(9), 2617; https://doi.org/10.3390/ijms19092617

Synthesis, Characterization, and Antimicrobial Properties of Peptides Mimicking Copolymers of Maleic Anhydride and 4-Methyl-1-pentene

1
DWI Leibniz Institute for Interactive Materials and Institute of Technical and Macromolecular Chemistry, RWTH Aachen University, Forckenbeckstraße 50, D-52056 Aachen, Germany
2
Institut für Chemie, Universität Osnabrück, OMC, Barbarastraße 7, D-49076 Osnabrück, Germany
*
Authors to whom correspondence should be addressed.
Received: 9 August 2018 / Revised: 27 August 2018 / Accepted: 29 August 2018 / Published: 4 September 2018
(This article belongs to the Special Issue Polymeric Systems as Antimicrobial or Antifouling Agents)
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Abstract

Synthetic amphiphilic copolymers with strong antimicrobial properties mimicking natural antimicrobial peptides were obtained via synthesis of an alternating copolymer of maleic anhydride and 4-methyl-1-pentene. The obtained copolymer was modified by grafting with 3-(dimethylamino)-1-propylamine (DMAPA) and imidized in a one-pot synthesis. The obtained copolymer was modified further to yield polycationic copolymers by means of quaternization with methyl iodide and dodecyl iodide, as well as by being sequentially quaternized with both of them. The antimicrobial properties of obtained copolymers were tested against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus epidermidis, and Staphylococcus aureus. Both tested quaternized copolymers were more active against the Gram-negative E. coli than against the Gram-positive S. aureus. The copolymer modified with both iodides was best when tested against E. coli and, comparing all three copolymers, also exhibited the best effect against S. aureus. Moreover, it shows (limited) selectivity to differentiate between mammalian cells and bacterial cell walls. Comparing the minimum inhibitory concentration (MIC) of Nisin against the Gram-positive bacteria on the molar basis instead on the weight basis, the difference between the effect of Nisin and the copolymer is significantly lower. View Full-Text
Keywords: cationic polymers; imidization; quaternization; antimicrobial properties; hemolytic activity cationic polymers; imidization; quaternization; antimicrobial properties; hemolytic activity
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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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Szkudlarek, M.; Heine, E.; Keul, H.; Beginn, U.; Möller, M. Synthesis, Characterization, and Antimicrobial Properties of Peptides Mimicking Copolymers of Maleic Anhydride and 4-Methyl-1-pentene. Int. J. Mol. Sci. 2018, 19, 2617.

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