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ChemMedChem. 2014 Jul;9(7):1368-73. doi: 10.1002/cmdc.201300506. Epub 2014 Mar 5.

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

Author information

1
Center for Systems Biology, Massachusetts General Hospital, Richard B. Simches Research Center, 185 Cambridge Street, Boston, MA 02114 (USA).

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.

KEYWORDS:

BODIPY; fluorescence; fluorine-18; molecular imaging; positron emission tomography

PMID:
24596307
PMCID:
PMC4145401
DOI:
10.1002/cmdc.201300506
[Indexed for MEDLINE]
Free PMC Article

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