Calixarene - lipid monolayers: towards enzymatic engineering of lipid membranes.

Ewa M. Rogalska 1Beata Korchowiec 2Adel Ben Salem 1Yohann Corvis 1Jean-Bernard Regnouf de Vains 1Jacek Korchowiec 3

1. Universite Henri Poincare (UHP), Faculté des Sciences, BP 239, Nancy 54506, France
2. Jagiellonian University, Faculty of Chemistry, Department of Chemical Physics, Ingardena 3, Kraków 30-060, Poland
3. Jagiellonian University, Faculty of Chemistry, Ingardena 3, Kraków 30-060, Poland

Abstract

Three new antimicrobial p-tert-butylcalix[4]arene derivatives were studied in a membrane environment, using 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (DMPE) and 1,2-dilauroyl-sn-glycero-3-phosphocholine (DLPC) monolayers; the aim of this study was getting some insight in the relation between the membrane structure and the activity of lipolytic enzymes. The derivatives used have 6-aminopenicillanic acid or benzylpenicillin moieties grafted in alternate positions at the calixarene lower rim. The miscibility of calixarene-antibiotic conjugates with lipid films was studied using surface pressure and surface potential measurements, as well as Brewster angle microscopy. Molecular modeling allowed assessing the lowest energy conformations of the calixarene derivatives and gave more insight in the interactions with the lipid films. The results obtained show that the 6-aminopenicillanic acid derivative decreases the molecule packing in the mixed films compared to the benzylpenicillin derivatives; the decreased molecule packing is accompanied by an increased ordering of the DMPE molecules in the lipid-rich phase. Moreover, the 6-aminopenicillanic acid derivative affects the activity of phospholipase A2 (PLA2) catalyzing the hydrolysis of the DLPC monolayer. It may be supposed that the adjustment of the activity of PLA2 is due to the modifications of the film structure, which influences in turn the process of binding of the enzyme to the substrate surface. The results obtained in this work will be used to develop methods of a controlled enzymatic engineering of selective lipid membranes.

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Presentation: Keynote lecture at SMCBS'2007 International Workshop, by Ewa M. Rogalska
See On-line Journal of SMCBS'2007 International Workshop

Submitted: 2007-08-03 18:25
Revised:   2009-06-07 00:44
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