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摘要
The efficient transformation of the hexadentate bispidinol 1 into carbamate derivatives yields functional bispidines enabling convenient functionalization for targeted imaging. The BODIPY-substituted bispidine 3 combines a coordination site for metal ions, such as radioactive Cu-64(II), with a fluorescent unit. Product 3 was thoroughly characterized by standard analytical methods, single crystal X-ray diffraction, radiolabeling, and photophysical analysis. The luminescence of ligand 3 was found to be strongly dependent on metal ion coordination: Cu-II quenches the BODIPY fluorescence, whereas N-II and Zn-II ions do not affect it. It follows that, in imaging applications with the positron emitter Cu-64(II), residues of its origin from enriched Ni-64 and the decay products N-64(III) and 64Zn(II), efficiently restore the fluorescence of the ligand. This allows for monitoring of the emitted radiation as well as the fluorescence signal. The stability of the Cu-64(II)-3 complex is investigated by transmetalation experiments with Zn-II and N-III, using fluorescence and radioactivity detection, and the results confirm the high stability of Cu-64(II)-3. In addition, metal complexes of ligand 3 with the lanthanide ions Tb-III, Eu-III, and Nd-III are shown to exhibit emission of the BODIPY ligand and the lanthanide ion, thus enabling dual emission detection.
- 出版日期2014-12-15
