Diamidodipyrrins as BODIPY dyes and chelator fragment libraries to identify new scaffolds for metalloprotein inhibitors

The thesis presented here is split between two distinct projects. The first project explores the synthesis and photophysical evaluation of a new class of BODIPY dyes with handles for functionalization. These dyes may be easily modified for use in biological systems. The BODIPY dyes were synthesized by simple modifications of reported procedures and were evaluated using luminescence and UV-visible spectroscopy. An X-ray diffraction crystal structure and 19F NMR data indicate that these dyes are rigidified by intramolecular hydrogen bonding.;The second project is directed towards studying the utility of a chelator fragment library in indentifying new metal-binding groups for metalloprotein inhibitors. The chelator fragment library was screened at high concentration in cell-free bioassays against several types of metalloenzymes to yield several new metal-binding scaffolds that result in significant enzyme inhibition. One of these scaffolds was synthetically elaborated at multiple positions to demonstrate the effect of the chelator in a fragment growth strategy.