Thiabicyclononane-Based
Antimicrobial Polycations
Posted on 2017-10-19 - 20:45
Bicyclo[3.3.1]nonane
(BCN) polycations were synthesized by the
reaction of the bivalent electrophile thiabicyclo[3.3.1]nonane dinitrate
with a series of simple bis(pyridine) nucleophiles. Oligomers of moderate
chain length were formed in a modular approach that tolerated the
inclusion of functionalized and variable-length linkers between the
pyridine units. Post-polymerization modification via copper-catalyzed
azide–alkyne cyloaddition was enabled by the inclusion of terminal
alkyne groups in these monomers. Most of the resulting polymers, new
members of the polyionene class, inhibited the growth of bacteria
at the μg/mL level and killed static bacterial cells at polymer
concentrations of tens of ng/mL, with moderate to good selectivity
with respect to lysis of red blood cells. While resistance to the
BCN polymers was developed only very slowly over multiple passages,
a degradable version of the polycation was observed to make E. coli cells more susceptible to other quaternary ammonium
based antimicrobials. Solid substrates (glass and crystalline silicon)
covalently functionalized with a representative BCN polycation were
also able to repetitively kill bacteria in solution at high rates
and with cleaning by simple sonication between exposures.
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Geng, Zhishuai; Finn, M. G. (2017). Thiabicyclononane-Based
Antimicrobial Polycations. ACS Publications. Collection. https://doi.org/10.1021/jacs.7b07596
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