Thiabicyclononane-Based
Antimicrobial Polycations
Zhishuai Geng
M. G. Finn
10.1021/jacs.7b07596.s001
https://acs.figshare.com/articles/journal_contribution/Thiabicyclononane-Based_Antimicrobial_Polycations/5518837
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 <i>E. coli</i> 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.
2017-10-19 20:45:05
chain length
covalently functionalized
variable-length linkers
representative BCN polycation
coli cells
terminal alkyne groups
bacteria
inclusion
blood cells
BCN polymers
polyionene class
Post-polymerization modification
polymer concentrations
degradable version
pyridine units
Solid substrates
quaternary ammonium