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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
Iodomethane-12C, ≥99.9 atom % 12C, ≥99% (CP), contains copper as stabilizer
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Triethylamine, ≥99.5%
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Bis(trichloromethyl) carbonate, purum, ≥99.0% (AT)
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1,8-Diazabicyclo[5.4.0]undec-7-ene, puriss., ≥99.0% (GC)
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Tetrahydrofuran, analytical standard
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Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free
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1,8-Diazabicyclo[5.4.0]undec-7-ene, 98%
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Iodomethane, contains copper as stabilizer, ReagentPlus®, 99.5%
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Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%
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