A New Fluorescent Probe for Studies of Interactions Between Hydrophobic Oligonucleotides and Cellular Membranes

Abstract

The synthesis of a new fluorescently labeled medium-sensitive lipophilic oligonucleotide is reported. A fluorescent chalcone chromophore was introduced between the 5′ end of the nucleic acid and the fatty hydrocarbon chains. A blue shift of both absorption and emission wavelength maxima results from a transfer of the chromophore to a more hydrophobic medium or upon binding of the conjugate to unilamellar vesicles of egg phosphatidyl choline. These conjugates could be used as markers for cell uptake studies of lipophilic nucleic acid derivatives.