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Pyrenemethyl ara ‐Uridine‐2′‐carbamate: A Strong Interstrand Excimer in the Major Groove of a DNA Duplex

2003; Wiley; Volume: 4; Issue: 9 Linguagem: Inglês

10.1002/cbic.200300678

1439-7633

Natalia N. Dioubankova, Andrei D. Malakhov, Dmitry A. Stetsenko, Michael J. Gait, Pavel E. Volynsky, Roman G. Efremov, Vladimir A. Korshun,

Cancer therapeutics and mechanisms

Abstract The synthesis of new nucleoside derivatives , ara ‐uridine‐2′‐carbamates, and their incorporation into synthetic DNA oligomers is described. The modification directs ligands into the major groove of duplex DNA and somewhat destabilizes the duplexes of modified oligonucleotides with complementary DNA or RNA. In the case of pyrenemethyl carbamate modification in DNA–DNA duplexes, the destabilization is considerably reduced. The pyrenemethyl derivative also shows remarkable spectral properties: a 'reversed' absorbance change for pyrene at 350 nm in the course of denaturation of the DNA duplex, as compared to the change seen in the nucleotide absorbance at 260 nm. This derivatization also causes pronounced sequence‐dependent excimer formation in the major groove.