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

ABSTRACT: 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 (18) F-labeled BODIPY-FL fluorophore has emerged as an important platform, but little is known about alternative (18) F-labeling strategies or labeling on red-shifted fluorophores. In this study we explore acid-catalyzed (18) F/(19) F exchange on a range of commercially available N-hydroxysuccinimidyl ester and maleimide BODIPY fluorophores. We show this method to be a simple and efficient (18) F-labeling strategy for a diverse span of fluorescent compounds, including a BODIPY-modified PARP-1 inhibitor, and amine- and thiol-reactive BODIPY fluorophores.

SUBMITTER: Keliher EJ

PROVIDER: S-EPMC4145401 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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

Keliher Edmund J EJ Klubnick Jenna A JA Reiner Thomas T Mazitschek Ralph R Weissleder Ralph R

ChemMedChem 20140305 7

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 (18) F-labeled BODIPY-FL fluorophore has emerged as an important platform, but little is known about alternative (18) F-labeling strategies or labeling on red-shifted fluorophores. In this study we explore acid-catalyzed (18) F/(19) F exchange on a range of commercially available N-hydroxysuccin ...[more]

PMID: 24596307

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