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

被引:28
作者
Brizet, Bertrand [1 ,2 ]
Goncalves, Victor [1 ]
Bernhard, Claire [1 ]
Harvey, Pierre D. [2 ]
Denat, Franck [1 ]
Goze, Christine [1 ]
机构
[1] Univ Bourgogne, Inst Chim Mol, UMR 6302, F-21078 Dijon, France
[2] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
alkynes; click chemistry; fluorine; imaging agents; luminescence; radiochemistry; EMISSION-TOMOGRAPHY; DYES; CHEMISTRY; AGENTS; PEPTIDES; BOMBESIN; YIELD;
D O I
10.1002/chem.201402379
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several new boron dipyrromethene/N,N-dimethylaminopyridine (BODIPY-DMAP) assemblies were synthesized as precursors for bimodal imaging probes (optical imaging, I/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.
引用
收藏
页码:12933 / 12944
页数:12
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