A comparison of linear and cyclic peptoid oligomers as potent antimicrobial agents

Mia Lace Huang, Sung Bin Y Shin, Meredith A. Benson, Victor J. Torres, Kent Kirshenbaum

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)114-122
Number of pages9
JournalChemMedChem
Volume7
Issue number1
DOIs
StatePublished - Jan 2 2012

Fingerprint

Peptoids
Anti-Infective Agents
Oligomers
N-substituted Glycines
Cell growth
Gram-Negative Bacteria
Bacteria
Erythrocytes
Head
Growth

Keywords

  • Antibiotic resistance
  • Antimicrobial peptides
  • Foldamers
  • Macrocycles
  • Peptidomimetics

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry
  • Molecular Medicine

Cite this

A comparison of linear and cyclic peptoid oligomers as potent antimicrobial agents. / Huang, Mia Lace; Shin, Sung Bin Y; Benson, Meredith A.; Torres, Victor J.; Kirshenbaum, Kent.

In: ChemMedChem, Vol. 7, No. 1, 02.01.2012, p. 114-122.

Research output: Contribution to journalArticle

Huang, Mia Lace ; Shin, Sung Bin Y ; Benson, Meredith A. ; Torres, Victor J. ; Kirshenbaum, Kent. / A comparison of linear and cyclic peptoid oligomers as potent antimicrobial agents. In: ChemMedChem. 2012 ; Vol. 7, No. 1. pp. 114-122.
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