Synthesis of 5-(2,2'-bipyridinyl and 2,2'-bipyridinediiumyl)-2'-deoxyuridine nucleosides: precursors to metallo-DNA conjugates.
The synthesis of 2,2'-bipyridinyl-2'-deoxyuridine metal-chelator nucleosides (Bipy-dU) with either ethynyl or ethylenyl linkers was now been accomplished. These new nucleosides will permit the construction of a number of corresponding metallo-DNA conjugates where many types of metals can be complexed to the 2,2'-bipyridinyl chelator group and the resulting metallo-dU conjugates incorporated into DNA oligonucleotides. Additionally this paper also reports the synthesis of a di-N-alkylated bipyridinediiumyl-2'-deoxyuridine nucleoside (Bipy(2+)-dU) with an ethylenyl linker. The Bipy(2+)-dU nucleoside was found to decompose under basic conditions precluding its use in standard automated DNA-synthesis by the phosphoramidite method. No such restrictions apply to the two Bipy-dU nucleosides reported here for use as metal chelators.
Gaballah
Samir T
ST
Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA.
Kerr
Charles E
CE
Eaton
Bruce E
BE
Netzel
Thomas L
TL
D002614:Chelating Agents / Q000138:chemical synthesis; D004247:DNA / Q000138:chemical synthesis*; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D009705:Nucleosides / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000138:chemical synthesis*
D002614:Chelating Agents; D003853:Deoxyribonucleosides; D009705:Nucleosides; D009942:Organometallic Compounds; D004247:DNA; D003857:Deoxyuridine