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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-¹²C, 99.95 atom % ¹²C

Sigma-Aldrich

Propionic acid, ACS reagent, ≥99.5%

Sigma-Aldrich

Pyridine, ≥99%

Sigma-Aldrich

Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer

Sigma-Aldrich

α-Bromoisobutyryl bromide, 98%

Sigma-Aldrich

Ethyl alcohol, Pure, 200 proof, anhydrous, ≥99.5%

Sigma-Aldrich

DCC, 99%

Sigma-Aldrich

p-Toluenesulfonic acid monohydrate, ACS reagent, ≥98.5%

Sigma-Aldrich

p-Toluenesulfonic acid monohydrate, ReagentPlus^®, ≥98%

Sigma-Aldrich

4-(Dimethylamino)pyridine, ReagentPlus^®, ≥99%

Sigma-Aldrich

Toluene, anhydrous, 99.8%

Sigma-Aldrich

Pyridine, LR, ≥99%

Sigma-Aldrich

Pyridine, AR, ≥99.5%

Sigma-Aldrich

Dichloromethane, AR, ≥99%

Sigma-Aldrich

Dichloromethane, LR, ≥99.5%

Sigma-Aldrich

Toluene, suitable for HPLC, ≥99.9%

Supelco

Methanol solution, contains 0.10 % (v/v) formic acid, UHPLC, suitable for mass spectrometry (MS), ≥99.5%

Sigma-Aldrich

Ethyl alcohol, Pure, 190 proof, ACS reagent, meets USP testing specifications, Excise Tax-free, Permit for use required

Sigma-Aldrich

Ethyl alcohol, Pure, 140 proof, Excise Tax-free, Permit for use required

Sigma-Aldrich

Ethyl alcohol, Pure, 140 proof, meets water USP testing specifications, Excise Tax-free, Permit for use required

Sigma-Aldrich

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

Sigma-Aldrich

Toluene, suitable for HPLC, ≥99.8%

Sigma-Aldrich

Toluene, LR, rectified, 99%

Sigma-Aldrich

p-Toluenesulfonic acid monohydrate, AR, ≥99%

Sigma-Aldrich

Toluene, AR, rectified, 99.5%

Sigma-Aldrich

Toluene, LR, ≥99%

Sigma-Aldrich

Toluene, LR, sulfur free, 99%

Sigma-Aldrich

Toluene, AR, ≥99.5%

Sigma-Aldrich

Propionic acid, BioReagent, suitable for insect cell culture, ~99%

Sigma-Aldrich

Pyridine, anhydrous, 99.8%