Synthesis of 5-(2,2'-bipyridinyl and 2,2'-bipyridinediiumyl)-2'-deoxyuridine nucleosides: precursors to metallo-DNA conjugates

Nucleosides Nucleotides Nucleic Acids. 2002;21(8-9):547-60. doi: 10.1081/NCN-120015068.

Abstract

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.

MeSH terms

  • Chelating Agents / chemical synthesis
  • DNA / chemical synthesis*
  • Deoxyribonucleosides / chemical synthesis*
  • Deoxyuridine / analogs & derivatives*
  • Deoxyuridine / chemical synthesis*
  • Nucleosides / chemical synthesis*
  • Organometallic Compounds / chemical synthesis*

Substances

  • Chelating Agents
  • Deoxyribonucleosides
  • Nucleosides
  • Organometallic Compounds
  • DNA
  • Deoxyuridine