Fabrication of self-assembled nanostructures with defined size and morphology
represents a formidable challenge and thus, has gained tremendous momentum in
research because of their potential applications in various biological
systems. Herein, we report on the synthesis of novel non-ionic amphiphiles
using 2,2-di(prop-2-yn-1-yl)propane-1,3-diol as a core further functionalized
with poly(ethylene glycol) monomethyl ether and alkyl chains employing a
chemo-enzymatic approach. Surface tension and fluorescence measurements along
with dynamic light scattering studies revealed that all of the amphiphilic
systems spontaneously self-assemble in aqueous solution, which is further
supplemented by cryogenic transmission electron microscopy. The solubilization
behavior of these systems as evidenced from UV-Vis and fluorescence
spectroscopy and high performance liquid chromatography suggested the
effective encapsulation of hydrophobic entities like Nile red, nimodipine,
curcumin and dexamethasone. A comparative study with a standard excipient,
Cremophor® ELP demonstrated that our nanocarriers exhibited
superior/equivalent solubilization behavior for curcumin. Confocal laser
scanning microscopy revealed efficient uptake of encapsulated dye in the
cytosol of lung cancer cells, thus suggesting, that the reported amphiphilic
systems can transport drugs into cells. A study of cytotoxicity showed that
the synthesized amphiphilic systems are non-cytotoxic at the concentrations
studied. The release profile of encapsulated Nile red incubated with/without a
hydrolase enzyme Candida antarctica lipase demonstrated that the dye is stable
in the amphiphilic nanostructures in the absence of enzyme for up to 12 days,
however, more than 90% release of the dye occurred in 12 days when incubated
with lipase. The results advocate the potential of these nanostructures as
prospective drug delivery vehicles