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The Selective Interactions of Cationic tetra-p-guanidinoethylcalix[4]arene With Lipid Membranes: Theoretical and Experimental Model Studies

The Selective Interactions of Cationic tetra-p-guanidinoethylcalix[4]arene With Lipid Membranes: Theoretical and Experimental Model Studies

Beata Korchowiec, Marcelina Gorczyca, Ewa Rogalska, Jean-Bernard Regnouf-de-Vains, Maxime Mourer, Jacek Korchowiec

Soft Matter. 2016 Jan 7;12(1):181-90.

PMID: 26451711

Abstract:

Behavior of cationic tetra-p-guanidinoethylcalix[4]arene (CX1) and its building block, p-guanidinoethylphenol (mCX1) in model monolayer lipid membranes was investigated using all atom molecular dynamics simulations and surface pressure measurements. Members of two classes of lipids were taken into account: zwitterionic 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and anionic 1,2-dimyristoyl-sn-glycero-3-phospho-l-serine sodium salt (DMPS) as models of eukaryotic and bacterial cell membranes, respectively. It was demonstrated that CX1 and mCX1 accumulate near the negatively charged DMPS monolayers. The adsorption to neutral monolayers was negligible. In contrast to mCX1, CX1 penetrated into the hydrophobic part of the monolayer. The latter effect, which is possible due to a flip-flop inversion of the CX1 orientation in the lipid layer compared to the aqueous phase, may be responsible for its antibacterial activity.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP105405503	1,2-Dimyristoyl-sn-glycero-3-phospho-L-serine sodium salt		105405-50-3	Price

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