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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)
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Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free
Supelco
Tetrahydrofuran, analytical standard
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Iodomethane, 2000 μg/mL in methanol: water (4:1), analytical standard
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Tetrahydrofuran, Selectophore, ≥99.5%
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Tetrahydrofuran, suitable for HPLC, ≥99.9%, inhibitor-free
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Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%
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Tetrahydrofuran, contains 250 ppm BHT as inhibitor, ACS reagent, ≥99.0%
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Triethylamine, ≥99.5%
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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)
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Triethylamine, ≥99%
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Iodomethane, purum, ≥99.0% (GC)
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Bis(trichloromethyl) carbonate, purum, ≥99.0% (AT)
Sigma-Aldrich
1,8-Diazabicyclo[5.4.0]undec-7-ene, 98%
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Iodomethane, contains copper as stabilizer, ReagentPlus®, 99%
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Iodomethane, contains copper as stabilizer, ReagentPlus®, 99.5%
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Tetrahydrofuran, ReagentPlus®, ≥99.0%, contains 250 ppm BHT as inhibitor
Sigma-Aldrich
Tetrahydrofuran, contains 250 ppm BHT as inhibitor, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.9%
Supelco
Triethylamine, analytical standard
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Tetrahydrofuran, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Tetrahydrofuran, ACS reagent, ≥99.0%, contains 250 ppm BHT as inhibitor
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Tetrahydrofuran, contains 250 ppm BHT as inhibitor, ACS reagent, ≥99.0%
Sigma-Aldrich
Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer
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Dichloromethane, analytical standard
Supelco
Dichloromethane, Selectophore, ≥99.5%