The hydrophobic core effect in model bacterial membranes upon interaction with tetra-p-guanidinoethylcalix[4]arene

[Display omitted] •An antibacterial calixarene derivative is incorporated in lipid monolayers.•Stable adducts are formed between the calixarene and medium chain lipids.•Tetra-p-guanidinoethylcalix[4]arene has no affinity for unsaturated phosphoglycerol.•The transfer of the calixarene from water to t...

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Bibliographic Details
Published in:Journal of molecular liquids 2021-12, Vol.343, p.117636, Article 117636
Main Authors: Korchowiec, Beata, Orlof-Naturalna, Monika, Korchowiec, Jacek, de Vains, Jean-Bernard Regnouf, Mourer, Maxime, Rogalska, Ewa
Format: Article
Language:English
Subjects:
Antibacterials
Calixarene
Chemical Sciences
Drug-membrane interaction
Life Sciences
Membrane penetration
Molecular modeling
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Summary:[Display omitted] •An antibacterial calixarene derivative is incorporated in lipid monolayers.•Stable adducts are formed between the calixarene and medium chain lipids.•Tetra-p-guanidinoethylcalix[4]arene has no affinity for unsaturated phosphoglycerol.•The transfer of the calixarene from water to the apolar region depends on the tail structure. The calixarene derivative used in this study (tetra-p-guanidinoethylcalix[4]arene) shows in vitro activity against different Gram-positive and Gram-negative bacteria. The interaction between bacterial cell membranes and the water-soluble calixarene was investigated using model lipids spread as monomolecular films at the air–water interface. Compression and adsorption experiments, as well as Brewster angle microscopy, polarization modulation-infrared reflection–absorption spectroscopy and computer modeling permitted understanding of the intra- and intermolecular interaction in several lipid-calixarene systems. Because the affinity of the calixarene derivative for the membranes may be linked to the interaction with negative charges, phosphatidylglycerols were used as model lipids; the phosphatidylglycerols contained saturated or unsaturated hydrocarbon chains with different lengths. It was showed that the affinity of the calixarene for the monolayer depends on the structure of the phosphatidylglycerols side chains. This observation may be of interest for a further development of new antibiotics.
ISSN:0167-7322
1873-3166
DOI:10.1016/j.molliq.2021.117636