Comparative Analysis of a Series of pH‐Responsive Sulphonated Europium Complexes for Bioassays Monitoring Acidification

Abstract

The synthesis and photophysical evaluation of a series of hydrophilic sulphonated and pH responsive luminescent europium(III) probes are reported. The Eu emission intensities and lifetimes increase very significantly on lowering pH, leading to a 'switching on' of Eu luminescence in more acidic media. By varying the nature of the substituents at an integral aniline nitrogen atom located in the sensitising chromophore, the pK a value of the complex can be tuned to between 4.3 and 6.3 for a set of five Eu(III) complexes. These systems are designed to allow conjugation to targeting vectors permitting, for example, the monitoring of receptor internalisation in cells. This approach can be used to tag proteins selectively and allows the monitoring of uptake into acidic organelles, enabling the creation of time-resolved internalisation assays to follow pH change in real time, both in vitro and in cellulo. Results and Discussion Ligand and complex synthesisMono-alkylation of 3-amino-4-methoxy-iodobenzene with the 3-bromopropyl-sulphonate ester, 1, proceeded in 63 % yield to [a