title: Calixarenes in a membrane environment: a monolayer study on the miscibility of three p-tert-butylcalix[4]arene beta-lactam derivatives with 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine.
abstract: Literature data indicate that some calixarene derivatives with antimicrobial activities may be useful as drugs; one of the aspects of the biological activity of different classes of antibiotics concerns interactions with lipid membranes. Here, the possibility of incorporation and/or translocation of three amphiphilic p-tert-butylcalix[4]arene derivatives across membranes was studied using lipid monolayers. The derivatives used have 6-aminopenicillanic acid or benzylpenicillin moieties grafted in alternate positions at the calixarene lower rim; 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (DMPE), a model bacterial membrane lipid, was used to prepare the monolayers. The miscibility of calixarene-antibiotic conjugates with lipid films was studied using surface pressure and surface potential measurements, as well as Brewster angle microscopy. The results obtained show that the miscibility is significantly different for the 6-aminopenicillanic acid and the two benzylpenicillin derivatives. Molecular modeling allowed the assessment of the lowest energy conformations of the calixarene derivatives and gave more insight into the interactions with the DMPE films.
authors.affiliation: Groupe d'Etude des Vecteurs Supramoléculaires du Médicament UMR 7565 CNRS/Université Henri Poincaré Nancy 1, Faculté des Sciences, BP 239, 54506 Vandoeuvre-lès-Nancy Cedex, France.
authors.forename: Beata
authors.initials: B
authors.lastname: Korchowiec
authors.forename: Adel
authors.initials: A
authors.lastname: Ben Salem
authors.forename: Yohann
authors.initials: Y
authors.lastname: Corvis
authors.forename: Jean-Bernard Regnouf
authors.initials: JB
authors.lastname: de Vains
authors.forename: Jacek
authors.initials: J
authors.lastname: Korchowiec
authors.forename: Ewa
authors.initials: E
authors.lastname: Rogalska
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D009682:Magnetic Resonance Spectroscopy; D008567:Membranes, Artificial; D008958:Models, Molecular; D010397:Penicillanic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D010714:Phosphatidylethanolamines / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D008567:Membranes, Artificial; D010714:Phosphatidylethanolamines; D047090:beta-Lactams; D047250:Calixarenes; D010397:Penicillanic Acid; C004408:aminopenicillanic acid; C018525:1,2-dimyristoylphosphatidylethanolamine