Efficient acid-catalyzed 18F/19F fluoride exchange of BODIPY dyes

Article abstract of DOI:10.1002/cmdc.201300506

Fluorine-containing fluorochromes are important validation agents for positron emission tomography imaging compounds, as they can be readily validated in cells by fluorescence imaging. In particular, the ¹⁸F-labeled BODIPY-FL fluorophore has emerged as an important platform, but little is known about alternative ¹⁸F-labeling strategies or labeling on red-shifted fluorophores. In this study we explore acid-catalyzed ¹⁸F/ ¹⁹F exchange on a range of commercially available N-hydroxysuccinimidyl ester and maleimide BODIPY fluorophores. We show this method to be a simple and efficient ¹⁸F-labeling strategy for a diverse span of fluorescent compounds, including a BODIPY-modified PARP-1 inhibitor, and amine- and thiol-reactive BODIPY fluorophores. A colorful exchange: In this study we explore acid-catalyzed ¹⁸F/¹⁹F exchange on a range of commercially available NHS ester and maleimide BODIPY fluorophores. We show this method to be a simple and efficient ¹⁸F-labeling strategy for a diverse range of fluorescent compounds, including a BODIPY-modified PARP-1 inhibitor, and amine- and thiol-reactive BODIPY fluorophores.