Para-carboxy modified amphiphilic calixarene, self-assembly and interactions with pharmaceutically-relevant molecules.
The self-assembly properties of the amphiphilic 5,11,17,23-tetra-carboxy-25,26,27,28-tetradodecyloxycalix[4]arene have been investigated at the air-water interface as monomolecular Langmuir layers and in water. The interactions of this amphiphile with salicylic acid (SA), acetyl-salicylic acid (ASA) and acetaminophene (APAP) have been studied at the air-water interface by means of the Langmuir balance technique. It has been demonstrated that the calix-arene molecules, when self-assembled as Langmuir monolayers, have the ability to interact with all the tested compounds. While APAP causes a stabilization of the monolayer, ASA and SA cause a slight loss of stability and a drastic change of the compressibility of the monolayer. The study of the self-assembly properties of the title compound in water revealed that this amphiphile can be self-assembled as solid lipid nanoparticles (SLNs). The atomic force microscopy investigations of the colloidal suspension, spread on a solid surface and dried, revealed the coexistence of the SLNs with layered structures.
University of Applied Sciences Northwestern Switzerland, School of Life Sciences, Institute of Chemistry and Bioanalytics, Gründenstrasse 40, CH-4132 Muttenz.
Dirk
D
Elend
Uwe
U
Pieles
Patrick
P
Shahgaldian
D000082:Acetaminophen / Q000737:chemistry*; D001241:Aspirin / Q000737:chemistry; D047250:Calixarenes / Q000138:chemical synthesis / Q000737:chemistry*; D018625:Microscopy, Atomic Force; D008855:Microscopy, Electron, Scanning; D015394:Molecular Structure; D053758:Nanoparticles / Q000737:chemistry*; D010316:Particle Size; D020156:Salicylic Acid / Q000737:chemistry*; D013499:Surface Properties; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*; D053835:Unilamellar Liposomes
C555692:5,11,17,23-tetra-carboxy-25,26,27,28-tetradodecyloxycalix(4)arene; D013501:Surface-Active Agents; D053835:Unilamellar Liposomes; D047250:Calixarenes; D000082:Acetaminophen; D020156:Salicylic Acid; D001241:Aspirin