Overcoming multidrug resistance in microbials using nanostructures self-assembled from cationic bent-core oligomers

Abstract

A study was conducted to report the synthesis, self-assembly and antimicrobial activity of a series of novel oligomeric cationic compounds of discrete molecular weights. These compounds were designed with a rigid hydrophobic terephthalamidebis urea core flanked by hydrophilic imidazolium groups with short alkyl or simple aryl tails, and were found to readily self-assemble into nanostructures in aqueous solutions. The cationic oligomer with optimal hydrophobic/hydrophilic balance showed potent, broad-spectrum antimicrobial activity and high selectivity towards Gram-positive bacteria, killing the microbes via the membrane-lytic mechanism. The key design element of our cationic antimicrobial oligomers was based on the rigid terephthalamide core generated via the organocatalytic aminolysis of poly(ethylene terephthalate) (PET) with 4-aminobenzylamine and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) .