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A Comparison of Linear and Cyclic Peptoid Oligomers as Potent Antimicrobial Agents
Author(s) -
Huang Mia Lace,
Shin Sung Bin Y.,
Benson Meredith A.,
Torres Victor J.,
Kirshenbaum Kent
Publication year - 2012
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201100358
Subject(s) - peptoid , antimicrobial , combinatorial chemistry , chemistry , stereochemistry , computational biology , peptide , biology , biochemistry , organic chemistry
We investigated the antimicrobial activities of N‐substituted glycine “peptoid” oligomers incorporating cationic and hydrophobic side chains. Head‐to‐tail macrocyclization was employed to enhance antimicrobial activity. Both linear and cyclic peptoids, ranging from six to ten residues, demonstrate potent antimicrobial activity against Gram‐positive and Gram‐negative bacteria. These peptoids do not cause significant lysis of human erythrocytes, indicating selective antimicrobial activity. Conformational ordering established upon macrocyclization is generally associated with an enhanced capacity to inhibit bacterial cell growth. Moreover, increased hydrophobic surface area also plays a role in improving antimicrobial activity. We demonstrate the potency of a cyclic peptoid in exerting antimicrobial activity against clinical strains of S. aureus while deterring the emergence of antimicrobial resistance.