Synthesis of hydrosoluble seleno- and telluro-BODIPY as fluorescent sensors for biological applications

Abstract

This project consists in the preparation of new chalcogen-containing near infrared (NIR) fluorescent BODIPY derivatives. The BODIPY Keio Fluors nuclei will be explored by functionalization with substituents containing selenium and tellurium conjugated to the chromophoric nucleus in order to obtain bathochromic shifts in the absorption/emission maxima (steric effect and heavy atom effect). The insertion of heavy atoms may lead to suppression of fluorescence by reductive photoinduced electron transfer (d-PeT). Thus, when the Se and Te atoms are oxidized to their corresponding chalcogenoxides/chalcogenones, the fluorescence will be reestablished to BODIPY nucleus allowing the use of the new chromophores as on/off-sensors. Thus, it is possible to detect endogenous reactive oxygen and nitrogen species (ROS, RNS) in vivo. The synthesis of the compounds will also contemplate functionalization steps with groups that influence the hydrophilicity. After characterization of the obtained molecules, the photophysical properties and the selectivity to detect analytes, such as metals and oxidants, will be studied. Finally, biochemical/biological studies will be initiated in search of applications for the new compounds. (AU)