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

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, NMR reference standard

Sigma-Aldrich

Triethylamine, ≥99%

Sigma-Aldrich

Chloroform, ≥99%, PCR Reagent, contains amylenes as stabilizer

Sigma-Aldrich

Triethylamine, ≥99.5%

Sigma-Aldrich

Hexadecyltrimethylammonium chloride, ≥98.0% (NT)

Sigma-Aldrich

Triethylamine, for protein sequence analysis, ampule, ≥99.5% (GC)

Sigma-Aldrich

Triethylamine, for amino acid analysis, ≥99.5% (GC)

Sigma-Aldrich

Triethylamine, BioUltra, ≥99.5% (GC)

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Triethylamine, puriss. p.a., ≥99.5% (GC)

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Benzaldehyde dimethyl acetal, 95%

Sigma-Aldrich

Methanol, anhydrous, 99.8%

Sigma-Aldrich

Diethyl ether

Sigma-Aldrich

Acetone, suitable for HPLC, ≥99.9%

Sigma-Aldrich

Benzaldehyde dimethyl acetal, ≥98%, FG

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Cetyltrimethylammonium chloride solution, 25 wt. % in H₂O

Sigma-Aldrich

Diethyl ether, contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%

Sigma-Aldrich

Chloroform, anhydrous, ≥99%, contains 0.5-1.0% ethanol as stabilizer

Sigma-Aldrich

Acetone, ≥99%, meets FCC analytical specifications

Sigma-Aldrich

Acetone, natural, ≥97%

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Triethylamine, ≥99.5%

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Benzaldehyde dimethyl acetal, 99%

Sigma-Aldrich

Chloroform, anhydrous, contains amylenes as stabilizer, ≥99%

Sigma-Aldrich

Methanol-¹²C, 99.95 atom % ¹²C

Sigma-Aldrich

Dimethyl ether, ≥99.9%

Sigma-Aldrich

Methanol solution, (Methanol:Dimethyl sulfoxide 1:1 (v/v))

Supelco

Methanol solution, NMR reference standard, 4% in methanol-d₄ (99.8 atom % D), NMR tube size 5 mm × 8 in.

Sigma-Aldrich

Dichloromethane, purification grade

Sigma-Aldrich

Methanol solution, NMR reference standard, 4% in methanol-d₄ (99.8 atom % D), NMR tube size 3 mm × 8 in.

Sigma-Aldrich

p-Toluenesulfonic acid monohydrate, ≥99% (calc. to H₂O free subst.)

Sigma-Aldrich

Pyridine, ≥99%