The Development Of Novel BODIPY-based Fluorescent Probes

Boron-dipyrromethene (BODIPY) dye, a new kind of excellent fluorescent dye, has high molar extinction coefficient and fluorescence quantum yield, high stablility of spectral properties, narrow fluorescence spectroscopy peak and high light stability, and its structure can be easily tuned. Thus it is widely used in the design of novel fluorescent probes. Introducing different active group to the BODIPY core, we can obtain different fluorescent probes. In this dissertation, we focus on the development of novel BODIPY-based viscosity and hypochlorite probes.In chapter2, we developed two novel fluorescent rotors based on a hybrid BODIPY-cyanine platform which can detect viscosity ratiometrically. With the increase of viscosity, the fluorescence at long wavelength increased dramastically, meanwhile, the fluorescence at short wavelength changed slightly. In addition, the bond between the rotor and the mother fluorophore in BDP-CY-1can be selectively cleaved by hypochlorite, resulting in a great increase in green fluorescence. Because of the highly diffusible and reactive nature of hypochlorite, overproduction in living organism killed cell, concomitant with a remarkable increase of cellular viscosity. This probe has the potential to be used to uncover the important role of hypochlorite in apoptosis.In chapter3, A novel red-emission BODIPY dye with a pyrrole ring was synthesized simply in one-pot reaction. Its spectral properties were investigated in different solvents. The BODIPY dye was extremely sensitive to solvent polarity. Its fluorescent emission enhanced with the decrease of solvent polarity. In aqueous buffer, the addition of bovine serum albumin led a ratiometric change in absorption spectra, with an association constant of1.16*106M-1. Meanwhile, the fluorescence emission at622nm increased greatly but little change at575nm. The response was very fast, less than3min, and noticeable by naked eyes. It allowed the detection of bovine serum albumin by a ratiometric fluorescence method. Other proteins or enzymes had no such responses. This was because that bovine serum albumin had suitable hydrophobic cavities to bind with the dye.