Influence of molecular structure on the antimicrobial function of phenylenevinylene conjugated oligoelectrolytes

Abstract

Structure/property relationships were obtained to understand the antimicrobial function of conjugated oligoelectrolytes toward Gram-negative and Gram-positive bacteria.

Informed Molecular Design of Conjugated Oligoelectrolytes To Increase Cell Affinity and Antimicrobial Activity

“…COE association and disruption is not driven by a charge‐based mechanism, as indicated by the sensitivity to COEs of AMP‐resistant mutant microbes that are unable to carry out charge‐based microbial‐envelope modifications . The length of the conjugated component in phenylenevinylene‐based structures modulates antimicrobial activity, and shorter COEs are typically more inhibitory . The MIC for Escherichia coli K12 decreases from 512 μ m to 64 μ m over a range of structural variations spanning five to three phenylene units.…”

“…Using the conventional molecular design, a COE with a stilbene core, namely COE2‐2 , was shown to have less antimicrobial activity (MIC=169 μg mL −1 ) than its distyryl benzene counterpart, COE2‐3 (MIC=11.4 μg mL −1 ), against E. coli K12 (Figure a) . Further analysis revealed that COE2‐2 had considerably weaker affinity for cell membranes relative to the longer molecules, likely because of its altered polar/hydrophobic profile.…”

Membrane permeabilization by conjugated oligoelectrolytes accelerates whole-cell catalysis

“…10,15,21,22 Despite its utility, the origin of DSSN+ improvement in bioelectrochemical devices remains under debate. 9,10,17,21,[23][24][25][26][27][28][29][30] Model membrane studies have shown that COEs increase ion conductance across the membrane.…”

“…1a), are of particular interest for their ability to modify membrane properties and improve performance of bioelectrochemical devices. 14,15 COEs have a p-delocalized backbone bearing ionic pendant groups and are known to spontaneously intercalate into lipid bilayers. COEs have shown to improve electrochemical performance in devices utilizing yeast, 13 Escherichia coli, 16 Shewanella oneidensis, 10,15 mixed communities, 17 and even membrane-based photosystems.…”

A Membrane‐Intercalating Conjugated Oligoelectrolyte with High‐Efficiency Photodynamic Antimicrobial Activity

“…It is also worth considering that the light penetration increases and light toxicity decreases with longer wavelengths . Most MICOEs absorb blue‐UV light, which limits their use in PDAT ,. We thus designed PTTP , see Scheme .…”