Crown ether modified peptides: Length and crown ring size impact on membrane interactions.

Autor: Paquet-Côté PA; Département de Chimie and PROTEO, Université Laval, 1045 avenue de la Médecine, Québec G1V 0A6, Canada., Paradis JP; Département de Chimie and PROTEO, Université Laval, 1045 avenue de la Médecine, Québec G1V 0A6, Canada., Auger M; Département de Chimie, CERMA and PROTEO, Université Laval, 1045 avenue de la Médecine, Québec G1V 0A6, Canada., Voyer N; Département de Chimie and PROTEO, Université Laval, 1045 avenue de la Médecine, Québec G1V 0A6, Canada. Electronic address: normand.voyer@chm.ulaval.ca.
Jazyk: angličtina
Zdroj: Biochimica et biophysica acta. Biomembranes [Biochim Biophys Acta Biomembr] 2020 Jul 01; Vol. 1862 (7), pp. 183261. Date of Electronic Publication: 2020 Mar 06.
DOI: 10.1016/j.bbamem.2020.183261
Abstrakt: Antimicrobial peptides are widely studied as an alternative to traditional antibiotics. However, they are difficult to develop, as multiple factors influence their potency and selectivity toward bacterial cells. In this paper, we investigate three simplified model peptides that bear crown ethers, and the effects of simple structural modifications (peptide length and crown ether ring size) on their secondary structures and their permeabilizing activity on living cells and model membranes made with egg yolk phosphatidylcholine or 1-palmitoyl-2-oleoylphosphatidylglycerol. Circular dichroism studies show that the peptide length and the crown ether ring size do influence the conformation, but no trend could be determined from the results. Permeabilization studies with model membranes and with red blood cells demonstrated that from 13 residues to 16 residues, there is a gradual increase in activity as the peptides get longer. However, the shortest tested analogs, with 12 residues, also exhibited an increase in activity caused by the removal of one amino acid that was bearing a crown ether. Permeabilization assays showed that larger ring size analogs showed higher hemolytic activities. Altogether, the results reported help design new and more selective antimicrobial peptides.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2020 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
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