mz200116k_si_001.pdf (1.23 MB)
Synthesis of Guanidinium Functionalized Polycarbodiimides and Their Antibacterial Activities
journal contribution
posted on 2012-03-20, 00:00 authored by Januka Budhathoki-Uprety, LingLing Peng, Christian Melander, Bruce M. NovakA family of guanidinium-side-chain functionalized polycarbodiimides
has been synthesized by allowing an azido guanidinium salt to react
with alkyne polycarbodiimides via the copper catalyzed [3 + 2] cycloaddition
(Click) reaction. Poly-2(a–d) are cationic/amphiphilic polymers in which the global hydrophilic/hydrophobic
balance has been tailored by local alteration of the length of alkyl
side chain in the repeat unit of polymers prior to polymerization.
The shorter alkyl chains yield water-soluble polymers, Poly-2c, -2d, and -2e. Antibacterial
activities of these cationic polycarbodiimides have been investigated
for Gram-positive and Gram-negative bacteria that include Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Escherichia
coli, and Acinetobacter baumannii. It was observed that the influence of hydrophobic–hydrophilic
balance per repeat unit of these polymers have profound effects for
both antimicrobial and hemolytic activities. In addition, these polycarbodiimide-guanidinium-triazole
conjugates offered moderate to significant antibacterial activity
and rapid interaction with red blood cells causing blood precipitation
without significant hemolysis in case of Poly-2(b–e). This latter property has
the potential to be exploited in the polymer coatings or wound protection.
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Antibacterial activitiescationic polycarbodiimidesalkyl side chainblood precipitationazido guanidinium saltblood cellsalkyne polycarbodiimidesAcinetobacter baumanniiwound protectionGuanidinium Functionalized PolycarbodiimidesStaphylococcus aureusMRSAalkyl chainspolymer coatingslatter propertyAntibacterial ActivitiesA family
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