Delivery of hydrophobic materials
in biological systems, for example,
contrast agents or drugs, is an obdurate challenge, severely restricting
the use of materials with otherwise advantageous properties. The synthesis
and characterization of a highly stable and water-soluble nanovesicle,
referred to as a quatsome (QS, vesicle prepared from cholesterol and
amphiphilic quaternary amines), that allowed the nanostructuration
of a nonwater soluble fluorene-based probe are reported. Photophysical
properties of fluorenyl–quatsome nanovesicles were investigated
via ultraviolet–visible absorption and fluorescence spectroscopy
in various solvents. Colloidal stability and morphology of the nanostructured
fluorescent probes were studied via cryogenic transmission electronic
microscopy, revealing a “patchy” quatsome vascular morphology.
As an example of the utility of these fluorescent nanoprobes, examination
of cellular distribution was evaluated in HCT 116 (an epithelial colorectal
carcinoma cell line) and COS-7 (an African green monkey kidney cell
line) cell lines, demonstrating the selective localization of C-QS and M-QS vesicles in lysosomes with high
Pearson’s colocalization coefficient, where C-QS and M-QS refer to quatsomes prepared with hexadecyltrimethylammonium
bromide or tetradecyldimethylbenzylammonium chloride, respectively.
Further experiments demonstrated their use in time-dependent lysosomal
tracking.