Hydrophobic interactions modulate antimicrobial peptoid selectivity towards anionic lipid membranes

Konstantin Andreev, Michael W. Martynowycz, Mia L. Huang, Ivan Kuzmenko, Wei Bu, Kent Kirshenbaum, David Gidalevitz

Research output: Contribution to journalArticle

Abstract

Hydrophobic interactions govern specificity for natural antimicrobial peptides. No such relationship has been established for synthetic peptoids that mimic antimicrobial peptides. Peptoid macrocycles synthesized with five different aromatic groups are investigated by minimum inhibitory and hemolytic concentration assays, epifluorescence microscopy, atomic force microscopy, and X-ray reflectivity. Peptoid hydrophobicity is determined using high performance liquid chromatography. Disruption of bacterial but not eukaryotic lipid membranes is demonstrated on the solid supported lipid bilayers and Langmuir monolayers. X-ray reflectivity studies demonstrate that intercalation of peptoids with zwitterionic or negatively charged lipid membranes is found to be regulated by hydrophobicity. Critical levels of peptoid selectivity are demonstrated and found to be modulated by their hydrophobic groups. It is suggested that peptoids may follow different optimization schemes as compared to their natural analogues.

Original languageEnglish (US)
Pages (from-to)1414-1423
Number of pages10
JournalBiochimica et Biophysica Acta - Biomembranes
Volume1860
Issue number6
DOIs
StatePublished - Jun 1 2018

Fingerprint

Peptoids
Membrane Lipids
Hydrophobic and Hydrophilic Interactions
Hydrophobicity
X-Rays
X rays
Peptides
Lipid bilayers
Atomic Force Microscopy
High performance liquid chromatography
Lipid Bilayers
Microbial Sensitivity Tests
Intercalation
Microscopy
Monolayers
Assays
Atomic force microscopy
High Pressure Liquid Chromatography

Keywords

  • AFM
  • Antimicrobial peptoids
  • Cytotoxicity
  • Hydrophobicity
  • Lipid membranes
  • X-ray scattering

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Cell Biology

Cite this

Hydrophobic interactions modulate antimicrobial peptoid selectivity towards anionic lipid membranes. / Andreev, Konstantin; Martynowycz, Michael W.; Huang, Mia L.; Kuzmenko, Ivan; Bu, Wei; Kirshenbaum, Kent; Gidalevitz, David.

In: Biochimica et Biophysica Acta - Biomembranes, Vol. 1860, No. 6, 01.06.2018, p. 1414-1423.

Research output: Contribution to journalArticle

Andreev, Konstantin ; Martynowycz, Michael W. ; Huang, Mia L. ; Kuzmenko, Ivan ; Bu, Wei ; Kirshenbaum, Kent ; Gidalevitz, David. / Hydrophobic interactions modulate antimicrobial peptoid selectivity towards anionic lipid membranes. In: Biochimica et Biophysica Acta - Biomembranes. 2018 ; Vol. 1860, No. 6. pp. 1414-1423.
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