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

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

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acids / chemistry*
  • Boron Compounds / chemistry*
  • Catalysis
  • Fluorine / chemistry*
  • Fluorine Radioisotopes / chemistry
  • Kinetics
  • Poly(ADP-ribose) Polymerase Inhibitors
  • Poly(ADP-ribose) Polymerases / metabolism
  • Positron-Emission Tomography
  • Sulfhydryl Compounds / chemistry

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Acids
  • Boron Compounds
  • Fluorine Radioisotopes
  • Poly(ADP-ribose) Polymerase Inhibitors
  • Sulfhydryl Compounds
  • Fluorine
  • Poly(ADP-ribose) Polymerases