title: The selective interactions of cationic tetra-p-guanidinoethylcalix[4]arene with lipid membranes: theoretical and experimental model studies.
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.
authors.affiliation: Department of Physical Chemistry and Electrochemistry, Faculty of Chemistry, Jagiellonian University, ul. R. Ingardena 3, 30-060 Krakow, Poland. bkorch@chemia.uj.edu.pl.
authors.forename: Beata
authors.initials: B
authors.lastname: Korchowiec
authors.affiliation: Department of Theoretical Chemistry, Faculty of Chemistry, Jagiellonian University, ul. R. Ingardena 3, 30-060 Krakow, Poland. korchow@chemia.uj.edu.pl.
authors.forename: Marcelina
authors.initials: M
authors.lastname: Gorczyca
authors.affiliation: Structure et Réactivité des Systèmes Moléculaires Complexes, BP 239, CNRS/Université de Lorraine, 54506 Vandoeuvre-lès-Nancy cedex, France.
authors.forename: Ewa
authors.initials: E
authors.lastname: Rogalska
authors.affiliation: Structure et Réactivité des Systèmes Moléculaires Complexes, BP 239, CNRS/Université de Lorraine, 54506 Vandoeuvre-lès-Nancy cedex, France.
authors.forename: Jean-Bernard
authors.initials: JB
authors.lastname: Regnouf-de-Vains
authors.affiliation: Structure et Réactivité des Systèmes Moléculaires Complexes, BP 239, CNRS/Université de Lorraine, 54506 Vandoeuvre-lès-Nancy cedex, France.
authors.forename: Maxime
authors.initials: M
authors.lastname: Mourer
authors.affiliation: Department of Theoretical Chemistry, Faculty of Chemistry, Jagiellonian University, ul. R. Ingardena 3, 30-060 Krakow, Poland. korchow@chemia.uj.edu.pl.
authors.forename: Jacek
authors.initials: J
authors.lastname: Korchowiec
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D004134:Dimyristoylphosphatidylcholine / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D008051:Lipid Bilayers / Q000737:chemistry*; D056004:Molecular Dynamics Simulation; D014494:Unithiol / Q000737:chemistry
chemical_list: D008051:Lipid Bilayers; C524784:para-guanidinoethylcalix(4)arene; D047250:Calixarenes; D014494:Unithiol; D004134:Dimyristoylphosphatidylcholine