The poor uptake of fluorescent probesa nd therapeutics by mammalian cells is am ajor concern in biological applicationsr anging from fluorescencei maging to drug delivery in living cells. Although gaseous molecules such as oxygen and carbon dioxide, hydrophobic substances such as benzene, and small polar but uncharged molecules such as water ande thanolc an cross the cell plasma membrane by simple passived iffusion, many synthetic as well as biological molecules require specific membrane transporters and channel proteins that control the traffic of these molecules into and out of the cell. This work reports that the introduction of halogen atoms into as eries of fluorescent molecules remarkably enhances their cellular uptake, and that their trans-port can be increased to more than 95 %b yi ntroducing two iodine atoms at appropriate positions. The nature of the fluorophore does not play am ajor role in the cellular uptake when iodine atoms are presenti nt he molecules, as compoundsb earing naphthalimide, coumarin, BODIPY, and pyrene moieties shows imilar uptakes.I nterestingly,t he introduction of am aleimide-based fluorophore bearing two hydroxyethylthio moieties allows the molecules to cross the plasma and nuclear membranes, and the presence of iodine atoms furthere nhances the transport across both membranes. Overall, this study provides ag eneral strategy for enhancingt he uptake of organic molecules by mammalian cells.
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