Cyclization Improves Membrane Permeation by Antimicrobial Peptoids

Konstantin Andreev, Michael W. Martynowycz, Andrey Ivankin, Mia L. Huang, Ivan Kuzmenko, Mati Meron, Binhua Lin, Kent Kirshenbaum, David Gidalevitz

Research output: Contribution to journalArticle

Abstract

The peptidomimetic approach has emerged as a powerful tool for overcoming the inherent limitations of natural antimicrobial peptides, where the therapeutic potential can be improved by increasing the selectivity and bioavailability. Restraining the conformational flexibility of a molecule may reduce the entropy loss upon its binding to the membrane. Experimental findings demonstrate that the cyclization of linear antimicrobial peptoids increases their bactericidal activity against Staphylococcus aureus while maintaining high hemolytic concentrations. Surface X-ray scattering shows that macrocyclic peptoids intercalate into Langmuir monolayers of anionic lipids with greater efficacy than for their linear analogues. It is suggested that cyclization may increase peptoid activity by allowing the macrocycle to better penetrate the bacterial cell membrane.

Original languageEnglish (US)
Pages (from-to)12905-12913
Number of pages9
JournalLangmuir
Volume32
Issue number48
DOIs
StatePublished - Dec 6 2016

Fingerprint

Peptoids
Cyclization
Permeation
membranes
Membranes
bioavailability
staphylococcus
monomolecular films
Peptidomimetics
peptides
lipids
flexibility
selectivity
Cell membranes
entropy
analogs
X ray scattering
Lipids
Peptides
Monolayers

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

Cite this

Andreev, K., Martynowycz, M. W., Ivankin, A., Huang, M. L., Kuzmenko, I., Meron, M., ... Gidalevitz, D. (2016). Cyclization Improves Membrane Permeation by Antimicrobial Peptoids. Langmuir, 32(48), 12905-12913. https://doi.org/10.1021/acs.langmuir.6b03477

Cyclization Improves Membrane Permeation by Antimicrobial Peptoids. / Andreev, Konstantin; Martynowycz, Michael W.; Ivankin, Andrey; Huang, Mia L.; Kuzmenko, Ivan; Meron, Mati; Lin, Binhua; Kirshenbaum, Kent; Gidalevitz, David.

In: Langmuir, Vol. 32, No. 48, 06.12.2016, p. 12905-12913.

Research output: Contribution to journalArticle

Andreev, K, Martynowycz, MW, Ivankin, A, Huang, ML, Kuzmenko, I, Meron, M, Lin, B, Kirshenbaum, K & Gidalevitz, D 2016, 'Cyclization Improves Membrane Permeation by Antimicrobial Peptoids', Langmuir, vol. 32, no. 48, pp. 12905-12913. https://doi.org/10.1021/acs.langmuir.6b03477
Andreev K, Martynowycz MW, Ivankin A, Huang ML, Kuzmenko I, Meron M et al. Cyclization Improves Membrane Permeation by Antimicrobial Peptoids. Langmuir. 2016 Dec 6;32(48):12905-12913. https://doi.org/10.1021/acs.langmuir.6b03477
Andreev, Konstantin ; Martynowycz, Michael W. ; Ivankin, Andrey ; Huang, Mia L. ; Kuzmenko, Ivan ; Meron, Mati ; Lin, Binhua ; Kirshenbaum, Kent ; Gidalevitz, David. / Cyclization Improves Membrane Permeation by Antimicrobial Peptoids. In: Langmuir. 2016 ; Vol. 32, No. 48. pp. 12905-12913.
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