Design of Promising aza-BODIPYs for Bioimaging and Sensing

摘要

The obtainment of new luminophores for molecular sensorics of biosystems is becoming oneof the urgent tasks in the field of chemical synthesis. The solution to each practical problem imposesits own limitations in the design of new structures with practically useful properties. The relationshipbetween the structure and spectral properties is still to be unveiled. Three aza-BODIPY complexeswith substituents of different natures were studied using time-resolved and steady-state fluorescenceand absorption spectroscopy. The solvatochromic properties of aza-BODIPYs were studied withthe use of a combined polyparametric approach and analysis by chemoinformatics methods for thefirst time. It was found that red shift of aza-BODIPY dyes was due to the increase of their structurallability. Predictive and experimental methods showed that the investigated aza-BODIPYs exhibited apositive solvatochromic effect, in contrast to classic BODIPYs (bearing C in the meso-position of thedipyrromethene core), which represents the negative solvatochromic properties. Spectral maximain the area of the therapeutic window, low and predictable solvatochromism, and the ability tofine-tune the spectral characteristics make the investigated aza-BODIPYs promising scaffolds for theconstruction of bioengineering devices. Generalizations on the aza-BODIPYs’ design patterns weremade in accordance with further bioimaging applications.