6533b7ddfe1ef96bd127366c

RESEARCH PRODUCT

DMAP-BODIPY Alkynes: A Convenient Tool for Labeling Biomolecules for Bimodal PET-Optical Imaging

Bertrand BrizetBertrand BrizetClaire BernhardVictor GoncalvesFranck DenatPierre D. HarveyChristine Goze

subject

Boron CompoundsHalogenationPyridineschemistry.chemical_elementCatalysischemistry.chemical_compoundmedicineOrganic chemistrychemistry.chemical_classificationLuminescent Agentsmedicine.diagnostic_testLigand binding assayBiomoleculeOptical ImagingOrganic ChemistryGeneral ChemistryCombinatorial chemistrychemistryPositron emission tomographyAlkynesPositron-Emission TomographyClick chemistryFluorineBombesinClick ChemistryBODIPYLuminescencePreclinical imaging

description

Several new boron dipyrromethene/N,N-dimethylaminopyridine (BODIPY-DMAP) assemblies were synthesized as precursors for bimodal imaging probes (optical imaging, OI/positron emission tomography, PET). The photophysical properties of the new compounds were also studied. The first proof-of-concept was obtained with the preparation of several new BODIPY-labeled bombesins and evaluation of the affinity for bombesin receptors by using a competition binding assay. Fluorination reactions were investigated on DMAP-BODIPY precursors as well as on DMAP-BODIPY-labeled bombesins. Chemical modifications on the BODIPY core were also performed to obtain luminescent dyes emitting in the therapeutic window (650-900 nm), suitable for in vivo imaging, making these compounds promising precursors for PET/optical dual-modality imaging agents.

https://doi.org/10.1002/chem.201402379