Synthesis and analysis of small phthalimide-based chromophores for fluorescence detection of disease related substances

Abstract

A class of novel probes is expanded to explore its ability to detect a range of biologically important analytes. In this thesis, we have focused on two types of fluorophore which share the phthalimide structure within the fluorophore/chromophore core. Many other features including analyte selectivity differ with these probes based on the receptor site choice. Specifically, MPA intermediate fluorophores which contain the intact phthalimide structure appear to have three different positions for their possibility of detecting analytes as a probe and these alternations help change their structure and stability. And 1,8-naphthalimide structures have two quite obvious adjustable parts in their core body which, in conjunction with the active site choice, help improve the photophysical ability and structural stability of this probe type.

In our second chapter, we detect the nitroreductase with MPA intermediates fluorophore which contain the phthalimide structure. With these small sized molecules, we sought to detect, not just small analytes like ROS, biothiols, but also larger sized molecules like cell-contained important proteins which are involved in hypoxia and found in tumor cells. The given selectivity gave our molecules the ability to detect NTR sensitively and selectively.

In our third chapter, we derivatized the phthalimide probe for the intention of testing the molecule as a dual targeted probe, in which two different types of functional groups are present, which, respectively, are expected to undergo reaction with two different classes of analytes. Our compounds for synthesis were the ‘AND’ type dual targeting molecules give formula which contain the phenylselenyl group of for ROS detection and the tert-butyldiphenylsilyl (TBDPS) group intended for fluoride anion detection.

In the fourth chapter, we describe the detection of superoxide with a 1,8-naphthalimide structure as the fluorophore core. The compounds targeted for synthesis were the lysosome targeted probe with the 4-(2- aminoethyl)morpholine functional group and diphenylphosphinic group which were placed in to help detect superoxide. The selectivity of the cleavable group gave information about our molecules the ability to detect superoxide radical ions sensitively and selectively.