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| - Calixarenes in a Membrane Environment: A Monolayer Study on the Miscibility of Threep-tert-Butylcalix[4]arene β-Lactam Derivatives with1,2-Dimyristoyl-sn-glycero-3-phosphoethanolamine
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| - 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 lipidmembranes. 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 have6-aminopenicillanic acid or benzylpenicillin moieties grafted in alternate positions at the calixarene lowerrim; 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (DMPE), a model bacterial membrane lipid, was usedto prepare the monolayers. The miscibility of calixarene−antibiotic conjugates with lipid films was studiedusing surface pressure and surface potential measurements, as well as Brewster angle microscopy. The resultsobtained show that the miscibility is significantly different for the 6-aminopenicillanic acid and the twobenzylpenicillin derivatives. Molecular modeling allowed the assessment of the lowest energy conformationsof the calixarene derivatives and gave more insight into the interactions with the DMPE films.
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