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Issue 16, 2008
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Synthesis and photophysical properties of 7-deaza-2′-deoxyadenosines bearing bipyridine ligands and their Ru(II)-complexes in position 7

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Abstract

The synthesis of the title 7-deazaadenine 2′-deoxyribonucleosides bearing bipyridine, phenanthroline or terpyridine ligands linked to position 7 via an acetylene or phenylene spacer is reported based on aqueous cross-coupling reactions of unprotected 7-iodo-7-deaza-2′-deoxyadenosine with ligand-functionalized acetylenes or boronic acids. The aqueous cross-coupling with acetylene or boronate building blocks containing the Ru(bpy)3-type of complex gave the corresponding Ru-containing nucleosides. Photophysical and electrochemical properties were studied and the most efficient type of complex was selected for future luminescent and redox labelling of DNA. The title nucleosides also showed some cytostatic and anti-HCV activities.

Graphical abstract: Synthesis and photophysical properties of 7-deaza-2′-deoxyadenosines bearing bipyridine ligands and their Ru(ii)-complexes in position 7

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Publication details

The article was received on 03 Apr 2008, accepted on 13 May 2008 and first published on 16 Jun 2008


Article type: Paper
DOI: 10.1039/B805632C
Citation: Org. Biomol. Chem., 2008,6, 2852-2860
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    Synthesis and photophysical properties of 7-deaza-2′-deoxyadenosines bearing bipyridine ligands and their Ru(II)-complexes in position 7

    M. Vrábel, R. Pohl, I. Votruba, M. Sajadi, S. A. Kovalenko, N. P. Ernsting and M. Hocek, Org. Biomol. Chem., 2008, 6, 2852
    DOI: 10.1039/B805632C

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