Two antibacterial nalidixate calixarene derivatives in cholesterol monolayers: Molecular dynamics and physicochemical effects.

The interaction of two antibacterial calixarene derivatives with cholesterol, a eukaryotic cell membrane lipid, was investigated with the aim to get more insight in the potential advers effects on our cells. The derivatives used had one or two nalidixic acid arms grafted on the lower rim of the calixarene aromatic crown. Monomolecular films spread at the air-water interface were used as model lipid membranes.

Membrane activity of tetra-p-guanidinoethylcalix[4]arene as a possible reason for its antibacterial properties.

Tetra-p-guanidinoethylcalix[4]arene trifluoroacetate salt (CX1) was synthesized recently as an antibacterial agent. It showed to be active in vitro against various Gram-positive and Gram-negative bacteria. To get more insight in the mechanism of the biological activity of this derivative, it was studied upon interactions with model lipid membranes.

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.

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.