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DOI: 10.1055/s-0028-1083206
Synthesis and Spectroscopic Characterization of BODIPY-Modified Uridines as Potential Fluorescent Probes for Nucleic Acids
Publikationsverlauf
Received
9 June 2008
Publikationsdatum:
23. Oktober 2008 (online)
Abstract
BODIPY-modified nucleosides that contain the fluorophore attached to the 5-position of uridine via a short phenylene bridge have been prepared and characterized by optical spectroscopy and by electrochemistry. The target compounds were synthesized using a Pd-catalyzed cross-coupling of 4-formyl-phenylboronic acid to 5-iodo-2′-desoxyuridine, followed by acid-catalyzed formation of the BODIPY chromophore. The weakly electron-donating ethyl substituents in positions 2 and 6 of the BODIPY dye, shift both the absorption and emission properties of the corresponding modified uridines bathochromically and alter their redox properties. In contrast, exchange of the fluoro ligands at the boron center of the chromophores by methoxy groups does not change the optical properties but increases the electron-rich character of the BODIPY-modified uridines significantly.
Key words
absorption - BODIPY - cyclic voltammetry - fluorescence - nucleoside
