Role of hydrophobicity in tuning the intracellular uptake of dendron-based fluorophores for in vitro metal ion sensing.

Abstract

Fluorophores are used for sensing biologically relevant ions, toxic metals or pathogenic markers. However, the mode of entry of such fluorophores into the cell greatly depends on their size, shape, surface charge, functional groups, and hydrophobicity. In particular, the influence of hydrophobicity on the intracellular uptake of fluorophores is poorly investigated. Self-assembly is a recent strategy to tune the intracellular uptake of fluorophores, facilitating increased intracellular sensing and fluorescence. Herein, self-assembly of three novel poly(aryl ether) dendron derivatives that contain rhodamine units was used to investigate the effect of hydrophobicity on the intracellular uptake of self-assembled fluorophores. The results suggest that monomer hydrophobicity plays an important role in the uptake. The dendron-based fluorophores, which upon self-assembly, formed stable spherical aggregates ranging from 300 to 500 nm. The rhodamine-based dendrons could selectively sense Hg2+ ions in the presence of other competing metal cations. Intracellular imaging of the dendron-based fluorophores displayed bright red fluorescence in human embryonic kidney cells. The rate of intracellular uptake of the three dendron-based fluorophores was analyzed by flow cytometry. The results establish the importance of the hydrophilic-lipophilic balance of the self-assembled amphiphiles for tuning the intracellular uptake.