PMID: 11929265Apr 4, 2002Paper

Ru(II) and Os(II) nucleosides and oligonucleotides: synthesis and properties

Journal of the American Chemical Society
Dennis J Hurley, Yitzhak Tor

Abstract

A general and versatile method for the site-specific incorporation of polypyridine Ru(II) and Os(II) complexes into DNA oligonucleotides using solid-phase phosphoramidite chemistry is reported. Novel nucleosides containing a [(bpy)(2)M(3-ethynyl-1,10-phenanthroline)](2+) (M = Ru, Os) metal center covalently attached to the 5-position in 2'-deoxyuridine are synthesized, and their electrochemical as well as photophysical properties are studied. The Ru(II) nucleoside exhibits a rather long-lived excited state in phosphate buffer pH 7.0 (tau = 1.08 micros) associated with a relatively high emission quantum efficiency (phi = 0.051). The solvent dependence of the absorption and emission spectra is consistent with an emissive MLCT state where charge localization takes place on the extended heterocycle-linked phenanthroline. In contrast, the Os(II)-containing nucleoside is quite nonemissive in aqueous environment (tau = 0.027 micros, phi = 1 x 10(-4)). The metal-containing nucleosides are converted into their phosphoramidites and are utilized for the high-yield preparation of modified oligonucleotides. The novel oligonucleotides, characterized by absorption and emission spectroscopy, enzymatic digestion, and electrophoresis, form stabl...Continue Reading

References

Nov 12, 1993·Science·C J MurphyJ K Barton
Oct 3, 1999·Angewandte Chemie·H S JoshiY Tor
Mar 28, 1996·Chemical Reviews·Vincenzo BalzaniScolastica Serroni

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Citations

May 27, 2005·Organic & Biomolecular Chemistry·Clemens WagnerHans-Achim Wagenknecht
Nov 30, 2006·Chemistry : a European Journal·Mihaela CaprioaraAndres Jäschke
Jul 4, 2008·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Coralie Houarner-RassinFabrice Odobel
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Jun 1, 2011·Chemical Society Reviews·Michal Hocek, Miroslav Fojta
Feb 18, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Michael KarnahlSven Rau
Aug 15, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shuyu ZhangHui Wei
Oct 21, 2017·Chemistry : a European Journal·Tadao TakadaKazushige Yamana
Jan 11, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gil Tae Hwang
Jun 23, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marie FlammeMarcel Hollenstein
Mar 5, 2003·Chembiochem : a European Journal of Chemical Biology·O LentzenA Kirsch-De Mesmaeker
Nov 19, 2009·Chemistry : a European Journal·Anna Baccaro, Andreas Marx
Jul 12, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Surjendu Dey, Andres Jäschke
Mar 26, 2005·Chemical Communications : Chem Comm·B Ravindra BabuJesper Wengel
Nov 17, 2007·Journal of the American Chemical Society·Leslie-Anne FendtEugen Stulz
Mar 9, 2010·Chemical Reviews·Renatus W SinkeldamYitzhak Tor

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