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The Role of Charge Density and Hydrophobicity on the Biocidal Properties of Self-Protonable Polymeric Materials.

Macromolecular bioscience (2015-03-18)
Simona Matrella, Carmela Vitiello, Massimo Mella, Giovanni Vigliotta, Lorella Izzo
ABSTRACT

Intrinsic antimicrobial thermoplastic A(BC)n copolymers (n = 1, 2, 4), where A was poly(ethylene glycol) (PEG), BC was a random chain of methylmethacrylate (MMA), and alkyl-aminoethyl methacrylate (AAEMA), were synthesized and the antimicrobial activity and hemolyticity were evaluated on plaques obtained by casting as a function of the architecture, the N-substituent groups of the AAEMAs (methyl, ethyl, isopropyl, and tert-butyl groups) and the hydrophobic/charge density balance. Antimicrobial effectiveness and efficiency is controlled by the surface charge density and by the influence of N-alkyl groups on the surface morphology. Also interestingly, it is the absence of hemolitytic activity in all copolymers. In presence of Escherichia coli, the A(BC)2 copolymer with 40% of N-methyl groups is the most efficient, killing 91% of the bacteria already after 1.5 h.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methanol, anhydrous, 99.8%
Sigma-Aldrich
Ethyl alcohol, Pure, 190 proof, ACS spectrophotometric grade, 95.0%
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Methanol, HPLC Plus, ≥99.9%, poly-coated bottles
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Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer
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Toluene, anhydrous, 99.8%
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Triethylamine, ≥99.5%
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Pyridine, anhydrous, 99.8%
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Diethyl ether, contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%
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Triethylamine, ≥99%
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p-Toluenesulfonic acid monohydrate, ACS reagent, ≥98.5%
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Chloroform, anhydrous, ≥99%, contains 0.5-1.0% ethanol as stabilizer
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DCC, 99%
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4-(Dimethylamino)pyridine, ReagentPlus®, ≥99%
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Chloroform, anhydrous, contains amylenes as stabilizer, ≥99%
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Triethylamine, puriss. p.a., ≥99.5% (GC)
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Propionic acid, ACS reagent, ≥99.5%
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Triethylamine, BioUltra, ≥99.5% (GC)
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Diethyl ether
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Cetyltrimethylammonium chloride solution, 25 wt. % in H2O
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α-Bromoisobutyryl bromide, 98%
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p-Toluenesulfonic acid monohydrate, ReagentPlus®, ≥98%
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Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer
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Hexadecyltrimethylammonium chloride, ≥98.0% (NT)
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Dimethyl ether, ≥99%
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Acetone, suitable for HPLC, ≥99.9%
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Benzaldehyde dimethyl acetal, 99%
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p-Toluenesulfonic acid monohydrate, ≥99% (calc. to H2O free subst.)
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Propionic acid, ≥99.5%, FCC, FG
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Propionic acid, natural, 99%, FG
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Propionic acid, puriss. p.a., ≥99.5% (GC)