Effects of Cyclic vs. Acyclic Hydrophobic Subunits on the Chemical Structure and Biological Properties of Nylon-3 Co-Polymers

ACS Macro Letters
Saswata ChakrabortySamuel H Gellman

Abstract

Nylon-3 co-polymers containing both hydrophobic and cationic subunits can mimic the activity profile of host-defense peptides, if subunit identity and proportion are carefully selected. These sequence- and stereo-random co-polymers inhibit bacterial growth at relatively low concentrations, apparently via disruption of bacterial membranes, but they are relatively non-disruptive toward eukaryotic cell membranes (low hemolytic activity). In all previous examples, the hydrophobic subunits have contained cycloalkyl groups that incorporate the backbone Cα-Cβ bond. Here we have explored the effects of using analogous acyclic hydrophobic subunits. The results indicate that the replacing cyclic with acyclic hydrophobic subunits has a modest influence on biological properties. This influence appears to arise from differences in subunit flexibility.

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Citations

Dec 3, 2014·Advanced Drug Delivery Reviews·Victor W L NgJames L Hedrick
Mar 8, 2014·Journal of the American Chemical Society·Runhui LiuSamuel H Gellman
Oct 2, 2014·Journal of the American Chemical Society·Saswata ChakrabortySamuel H Gellman
Sep 28, 2015·Journal of Controlled Release : Official Journal of the Controlled Release Society·Jing LiDavid Oupický
Jul 10, 2017·ACS Biomaterials Science & Engineering·Emma WatsonAntonios G Mikos
Oct 9, 2017·ACS Biomaterials Science & Engineering·Steven MankociAbraham Joy

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