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

Autor(en): Szkudlarek, Marian
Heine, Elisabeth
Keul, Helmut
Beginn, Uwe 
Moeller, Martin
Stichwörter: ANTIBACTERIAL ACTIVITY; antimicrobial properties; AQUEOUS-SOLUTION PROPERTIES; Biochemistry & Molecular Biology; BIOCIDES; BIOLOGICALLY-ACTIVE POLYMERS; cationic polymers; Chemistry; Chemistry, Multidisciplinary; CORRESPONDING CATIONIC POLYMERS; FUNCTIONAL POLYMERS; hemolytic activity; imidization; MAIN-CHAIN; POLYMERIC PHOSPHONIUM SALTS; POLYURETHANE COATINGS; QUATERNARY AMMONIUM; quaternization
Erscheinungsdatum: 2018
Herausgeber: MDPI
Journal: INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
Volumen: 19
Ausgabe: 9
Zusammenfassung: 
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.
ISSN: 14220067
DOI: 10.3390/ijms19092617

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