Efficient Acid‐Catalyzed 18F/19F Fluoride Exchange of BODIPY Dyes. Issue 7 (5th March 2014)

• Record Type: Journal Article
• Authors: Keliher, Edmund J.; Klubnick, Jenna A.; Reiner, Thomas; Mazitschek, Ralph; Weissleder, Ralph
• Is Part Of: ChemMedChem. Volume 9:Issue 7(2014:Jul.)
• Page Start: 1368
• Page End: 1373
• Publication Date: 2014-03-05
• Subjects: Pharmaceutical chemistry -- Periodicals; 615.19005
• DOI: 10.1002/cmdc.201300506
• Languages: English
• ISSNs: 1860-7179

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>N</italic>‐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.</p> </abstract>