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  • Broad-spectrum antimicrobial polycarbonate hydrogels with fast degradability.

Broad-spectrum antimicrobial polycarbonate hydrogels with fast degradability.

Biomacromolecules (2015-03-13)
Ana Pascual, Jeremy P K Tan, Alex Yuen, Julian M W Chan, Daniel J Coady, David Mecerreyes, James L Hedrick, Yi Yan Yang, Haritz Sardon
ABSTRACT

In this study, a new family of broad-spectrum antimicrobial polycarbonate hydrogels has been successfully synthesized and characterized. Tertiary amine-containing eight-membered monofunctional and difunctional cyclic carbonates were synthesized, and chemically cross-linked polycarbonate hydrogels were obtained by copolymerizing these monomers with a poly(ethylene glycol)-based bifunctional initiator via organocatalyzed ring-opening polymerization using 1,8-diazabicyclo[5.4.0]undec-7-ene catalyst. The gels were quaternized using methyl iodide to confer antimicrobial properties. Stable hydrogels were obtained only when the bifunctional monomer concentration was equal to or higher than 12 mol %. In vitro antimicrobial studies revealed that all quaternized hydrogels exhibited broad-spectrum antimicrobial activity against Staphylococcus aureus (Gram-positive), Escherichia coli (Gram-negative), Pseudomonas aeruginosa (Gram-negative), and Candida albicans (fungus), while the antimicrobial activity of the nonquaternized hydrogels was negligible. Moreover, the gels showed fast degradation at room temperature (4-6 days), which makes them ideal candidates for wound healing and implantable biomaterials.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1,8-Diazabicyclo[5.4.0]undec-7-ene, puriss., ≥99.0% (GC)
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Triethylamine, for protein sequence analysis, ampule, ≥99.5% (GC)
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Triethylamine, BioUltra, ≥99.5% (GC)
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Triethylamine, for amino acid analysis, ≥99.5% (GC)
Supelco
Tetrahydrofuran, analytical standard
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Tetrahydrofuran, Selectophore, ≥99.5%
Sigma-Aldrich
Iodomethane-12C, ≥99.9 atom % 12C, ≥99% (CP), contains copper as stabilizer
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Triethylamine, ≥99.5%
Sigma-Aldrich
Triethylamine, ≥99.5%
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Tetrahydrofuran, inhibitor-free, suitable for HPLC, ≥99.9%
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Triethylamine, puriss. p.a., ≥99.5% (GC)
Sigma-Aldrich
Iodomethane, contains copper as stabilizer, ReagentPlus®, 99.5%
Sigma-Aldrich
Iodomethane, contains copper as stabilizer, ReagentPlus®, 99%
Sigma-Aldrich
1,8-Diazabicyclo[5.4.0]undec-7-ene, 98%
Sigma-Aldrich
Triethylamine, ≥99%
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Iodomethane, purum, ≥99.0% (GC)
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Bis(trichloromethyl) carbonate, purum, ≥99.0% (AT)
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Tetrahydrofuran, ACS reagent, ≥99.0%, contains 250 ppm BHT as inhibitor
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Triethylamine, analytical standard
Supelco
Tetrahydrofuran, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Tetrahydrofuran, contains 250 ppm BHT as inhibitor, ACS reagent, ≥99.0%
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Dichloromethane, analytical standard
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Dichloromethane, Selectophore, ≥99.5%
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N-Methyldiethanolamine, ≥99%
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Iodomethane solution, 2.0 M in tert-butyl methyl ether, contains copper as stabilizer
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Dichloromethane, suitable for HPLC, ≥99.8%, contains amylene as stabilizer
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Triphosgene, reagent grade, 98%
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Dichloromethane, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains 50-150 ppm amylene as stabilizer
Sigma-Aldrich
Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer
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