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Informed Molecular Design of Conjugated Oligoelectrolytes To Increase Cell Affinity and Antimicrobial Activity
Author(s) -
Zhou Cheng,
Chia Geraldine W. N.,
Ho James C. S.,
Seviour Thomas,
Sailov Talgat,
Liedberg Bo,
Kjelleberg Staffan,
Hinks Jamie,
Bazan Guillermo C.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201803103
Subject(s) - antimicrobial , conjugated system , minimum inhibitory concentration , chemistry , solubility , antibiotics , combinatorial chemistry , rational design , side chain , biochemistry , stereochemistry , nanotechnology , organic chemistry , materials science , polymer
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 μg 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 μg 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.