title: DMAP-BODIPY alkynes: a convenient tool for labeling biomolecules for bimodal PET-optical imaging.
abstract: 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.
authors.affiliation: Institut de Chimie Moléculaire de l'Université de Bourgogne, UMR 6302, 9, avenue Alain Savary, 21078 Dijon (France), Fax: (+33) 380-39-61-17; Départment de Chimie Université de Sherbrooke, Université de Sherbrooke, Québec, J1K 2R1 (Canada).
authors.forename: Bertrand
authors.initials: B
authors.lastname: Brizet
authors.forename: Victor
authors.initials: V
authors.lastname: Goncalves
authors.forename: Claire
authors.initials: C
authors.lastname: Bernhard
authors.forename: Pierre D
authors.initials: PD
authors.lastname: Harvey
authors.forename: Franck
authors.initials: F
authors.lastname: Denat
authors.forename: Christine
authors.initials: C
authors.lastname: Goze
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D001839:Bombesin / Q000032:analysis / Q000378:metabolism; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D057930:Click Chemistry; D054879:Halogenation; D049408:Luminescent Agents / Q000138:chemical synthesis / Q000737:chemistry*; D061848:Optical Imaging / Q000379:methods; D049268:Positron-Emission Tomography / Q000379:methods; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; C417980:4-(dimethylamine)pyridine; D000480:Alkynes; D001896:Boron Compounds; D049408:Luminescent Agents; D011725:Pyridines; D001839:Bombesin
keywords: alkynes; click chemistry; fluorine; imaging agents; luminescence; radiochemistry