title: 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.
authors.affiliation: Center for Systems Biology, Massachusetts General Hospital, Richard B. Simches Research Center, 185 Cambridge Street, Boston, MA 02114 (USA).
authors.forename: Edmund J
authors.initials: EJ
authors.lastname: Keliher
authors.forename: Jenna A
authors.initials: JA
authors.lastname: Klubnick
authors.forename: Thomas
authors.initials: T
authors.lastname: Reiner
authors.forename: Ralph
authors.initials: R
authors.lastname: Mazitschek
authors.forename: Ralph
authors.initials: R
authors.lastname: Weissleder
mesh_terms: D000143:Acids / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D005462:Fluorine Radioisotopes / Q000737:chemistry; D007700:Kinetics; D000067856:Poly(ADP-ribose) Polymerase Inhibitors; D011065:Poly(ADP-ribose) Polymerases / Q000378:metabolism; D049268:Positron-Emission Tomography; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D000143:Acids; D001896:Boron Compounds; D005462:Fluorine Radioisotopes; D000067856:Poly(ADP-ribose) Polymerase Inhibitors; D013438:Sulfhydryl Compounds; D005461:Fluorine; D011065:Poly(ADP-ribose) Polymerases
keywords: BODIPY; fluorescence; fluorine-18; molecular imaging; positron emission tomography