US EPA

4239815 

Journal Article 

Synthesis and evaluation of a [18F]BODIPY-labeled caspase-inhibitor 

Ortmeyer, CP; Haufe, G; Schwegmann, K; Hermann, S; Schäfers, M; Börgel, F; Wünsch, B; Wagner, S; Hugenberg, V 

2017 

Yes 

Bioorganic & Medicinal Chemistry
ISSN: 0968-0896
EISSN: 1464-3391 

25 

7 

2167-2176 

English 

28284866 

10.1016/j.bmc.2017.02.033 

BODIPYs (boron dipyrromethenes) are fluorescent dyes which show high stability and quantum yields. They feature the possibility of selective18F-fluorination at the boron-core. Attached to a bioactive molecule and labeled with [18F]fluorine, the resulting compounds are promising tracers for multimodal imaging in vivo and can be used for PET and fluorescence imaging. A BODIPY containing a phenyl and a hydroxy substituent on boron was synthesized and characterized. Fluorinated and hydroxy substituted dyes were coupled to an isatin-based caspase inhibitor via cycloaddition and the resulting compounds were evaluated in vitro in caspase inhibition assays. The metabolic stability and the formed metabolites were investigated by incubation with mouse liver microsomes and LC-MS analysis. Subsequently the fluorophores were labeled with [18F]fluorine and an in vivo biodistribution study using dynamic PET was performed.