Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes

Andreev, Konstantin; Bianchi, Christopher; Laursen, Jonas S.; Citterio, Linda; Hein-Kristensen, Line; Gram, Lone; Kuzmenko, Ivan; Olsen, Christian A.; Gidalevitz, David

doi:10.1016/j.bbamem.2014.05.022

Title: Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes

Journal Article · Wed Jan 01 00:00:00 EST 2014 · Biochimica et Biophysica Acta. Biomembranes

DOI:https://doi.org/10.1016/j.bbamem.2014.05.022· OSTI ID:1240735

Andreev, Konstantin; Bianchi, Christopher; Laursen, Jonas S.; Citterio, Linda; Hein-Kristensen, Line; Gram, Lone; Kuzmenko, Ivan; Olsen, Christian A.; Gidalevitz, David

Antimicrobial peptides or their synthetic mimics are a promising class of potential new antibiotics. Herein we assess the effect of the type of cationic side chain (i.e., guanidino vs. amino groups) on the membrane perturbing mechanismof antimicrobial α-peptide–β-peptoid chimeras. Langmuirmonolayers composed of 1,2-dipalmitoylsn- glycero-3-phosphatidylglycerol (DPPG) were used to model cytoplasmic membranes of both Gram-positive and Gram-negative bacteria,while lipopolysaccharide Kdo2-lipid Amonolayersweremimicking the outer membrane of Gram-negative species.We report the results of themeasurements using an array of techniques, including high-resolution synchrotron surface X-ray scattering, epifluorescence microscopy, and in vitro antimicrobial activity to study the molecularmechanisms of peptidomimetic interaction with bacterialmembranes.We found guanidino group-containing chimeras to exhibit greater disruptive activity on DPPGmonolayers than the amino group-containing analogues. However, this effect was not observed for lipopolysaccharidemonolayerswhere the difference was negligible. Furthermore, the addition of the nitrobenzoxadiazole fluorophore did not reduce the insertion activity of these antimicrobials into both model membrane systems examined, which may be useful for future cellular localization studies.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: National Institutes of Health (NIH); Danish Council for Independent Research; USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: AC02-06CH11357

OSTI ID:: 1240735

Journal Information:: Biochimica et Biophysica Acta. Biomembranes, Vol. 1838; ISSN 0005-2736

Publisher:: Elsevier

Country of Publication:: United States

Language:: English

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Guanidinium cation
Peptide–peptoid chimeras
Phosphatidylglycerol
X-ray scattering
antimicrobial peptidomimetics

Title: Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes

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