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

Membrane-intercalating conjugated oligoelectrolytes (COEs) are emerging as potential alternatives to conventional, yet increasingly ineffective, antibiotics. Three readily accessible COEs, belonging to an unreported series containing a stilbene core, namely D4, D6, and D8, were designed and synthesized so that the hydrophobicity increases with increasing side-chain length. Decreased aqueous solubility correlates with increased uptake by E. coli. The minimum inhibitory concentration (MIC) of D8 is 4 mg mL 1 against both E. coli and E. faecalis, with an effective uptake of 72 %. In contrast, the MIC value of the shortest COE, D4, is 128 mg mL 1 owing to the low cellular uptake of 3%. These findings demonstrate the application of rational design to generate efficacious antimicrobial COEs that have potential as low-cost antimicrobial agents.

Cheng Zhou, Geraldine W. N. Chia, James C. S. Ho, Thomas Seviour, Talgat Sailov, Bo Liedberg, Staffan Kjelleberg, Jamie Hinks, and Guillermo C. Bazan
Angewandte Chemie
Volume: 130
Pages: 8201–8204
Date: May, 2018
ICB Affiliated Authors: Guillermo C Bazan