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Synthesis 2008(22): 3657-3662  
DOI: 10.1055/s-0028-1083206
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Spectroscopic Characterization of BODIPY-Modified Uridines as Potential Fluorescent Probes for Nucleic Acids

Thomas Ehrenschwender, Hans-Achim Wagenknecht*
Institute for Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany
Fax: +49(941)9434617; e-Mail: achim.wagenknecht@chemie.uni-regensburg.de;
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Publication History

Received 9 June 2008
Publication Date:
23 October 2008 (online)

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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

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