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Efficient Acid‐Catalyzed 18 F/ 19 F Fluoride Exchange of BODIPY Dyes
Author(s) -
Keliher Edmund J.,
Klubnick Jenna A.,
Reiner Thomas,
Mazitschek Ralph,
Weissleder Ralph
Publication year - 2014
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201300506
Subject(s) - bodipy , fluorophore , fluorescence , chemistry , maleimide , amine gas treating , photochemistry , combinatorial chemistry , organic chemistry , physics , quantum mechanics
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.