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


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 C?-C? 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.

SUBMITTER: Chakraborty S 

PROVIDER: S-EPMC3856927 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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

Chakraborty Saswata S   Liu Runhui R   Lemke Justin J JJ   Hayouka Zvi Z   Welch Rodney A RA   Weisblum Bernard B   Masters Kristyn S KS   Gellman Samuel H SH  

ACS macro letters 20130801 8


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 conta  ...[more]

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