Surface modification of resorcinarene based self-assembled solid lipid nanoparticles for drug targeting

Abstract

Prolyl-bearing amphiphilic resorcinarenes, e.g. tetrakis(N-methylprolyl)tetraundecylcalix[4]resorcinarene, self-assemble as stable solid lipid nanoparticles; these fully characterized systems could be further functionalized at their surface with proteins, and interact with specific antibodies bound on a sensor surface.

Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles

“…Rather, all interaction in the lattice determine the conformation of the resorcinarene to provide optimal close 15 packing.…”

“…Depending on the structure, alkyl chain length and the cation, the complexes pack in shifted capsule, layer or bilayer assemblies. 15 C2BC5 has been previously crystallized as KPF 6 complex in a capsule assembly. 20 Now, another packing for C2BC5•2KPF 6 complex (C2K2) was obtained, forming layered packing without the capsule formation.…”

“…The volume of the suspension was adjusted to 50 ml giving the final nanoparticle concentration of 100 mg/L (or 0.1 mM). The hydrodynamic diameter of the nanoparticles was measured using dynamic light scattering (Beckman Coulter N5 Submicron Particle Size Analyzer) at 90° 15 angle in water using plastic cuvettes (3 min equilibration, 3 min measurement). Three samples for each SLN were measured.…”

“…Propyl, butyl, pentyl, heptyl, nonyl, decyl and undecyl groups at the 10 resorcinarene lower rim were chosen for structural comparison with the previously synthesized C2BC5 21,22 and to create amphiphilic bis-crowns. Synthesis was carried out in dry dimethyl formamide (DMF) using Cs 2 CO 3 and ditosylated tetra(ethylene glycol) yielding tetramethoxy resorcinarene bis- 15 crown ethers after purification as 15-30 % yields.…”

“…Since calixarenes and resorcinarenes are usually solid materials at room temperature, they can be used for preparation of solid lipid nanoparticles and studies of their potential in encapsulation of biologically important guests, DNA 60 for cell transfection and surface modification for drug targeting have been published. [14][15][16][17] Calixarenes and resorcinarenes with crown ether bridges connecting the hydroxyl groups are very selective cation receptors called calixcrowns. 18 Depending on the number of 65 oxygen donors and thus the length and geometry of the crown bridge, calixcrowns have very good affinity towards alkali and alkaline earth metal cations and ammonium ions.…”