Nucleoterpenes of thymidine and 2'-deoxyinosine: synthons for a biomimetic lipophilization of oligonucleotides

Chem Biodivers. 2013 Jan;10(1):39-61. doi: 10.1002/cbdv.201100338.


2'-Deoxyinosine (1) and thymidine (7) were N-alkylated with geranyl and farnesyl moieties. These hydrophobic derivatives, 3a and 3b, and 9a and 9b, respectively, represent the first synthetic biomimetic nucleoterpenes and were subsequently 5'-protected and converted into the corresponding 3'-O-phosphoramidites, 5a and 5b and 11a and 11b, respectively. The latter were used to prepare a series of lipophilized oligonucleotide dodecamers, a part of which were additionally labelled with indocarbocyanine fluorescent dyes (Cy3 or Cy5), 18-23. The insertion of the lipooligonucleotides into, as well as duplex formation at artificial lipid bilayers was studied by single-molecule fluorescence spectroscopy and fluorescence microscopy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetic Materials / chemical synthesis
  • Biomimetic Materials / chemistry*
  • Carbocyanines / chemistry
  • Inosine / analogs & derivatives*
  • Inosine / chemistry
  • Lipid Bilayers / chemistry
  • Lipid Bilayers / metabolism
  • Microscopy, Fluorescence
  • Oligonucleotides / chemistry*
  • Spectrometry, Fluorescence
  • Thymidine / chemistry*


  • Carbocyanines
  • Lipid Bilayers
  • Oligonucleotides
  • cyanine dye 3
  • cyanine dye 5
  • Inosine
  • deoxyinosine
  • Thymidine