General method for labeling siRNA by click chemistry with fluorine-18 for the purpose of PET imaging

Bioconjug Chem. 2011 Jan 19;22(1):108-14. doi: 10.1021/bc100263y. Epub 2010 Dec 21.


The alkyne-azide Cu(I)-catalyzed Huisgen cycloaddition, a click-type reaction, was used to label a double-stranded oligonucleotide (siRNA) with fluorine-18. An alkyne solid support CPG for the preparation of monostranded oligonucleotides functionalized with alkyne has been developed. Two complementary azide labeling agents (1-(azidomethyl)-4-[(18)F]fluorobenzene) and 1-azido-4-(3-[(18)F]fluoropropoxy)benzene have been produced with 41% and 35% radiochemical yields (decay-corrected), respectively. After annealing with the complementary strand, the siRNA was directly labeled by click chemistry with [(18)F]fluoroazide to produce the [(18)F]-radiolabeled siRNA with excellent radiochemical yield and purity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Click Chemistry*
  • Fluorine Radioisotopes*
  • Fluorobenzenes / chemistry
  • Isotope Labeling / methods*
  • Oligoribonucleotides / chemistry
  • Positron-Emission Tomography / methods*
  • RNA, Double-Stranded / chemistry
  • RNA, Small Interfering / chemistry*


  • 1-(azidomethyl)-4-((18)F)-fluorobenzene
  • Alkynes
  • Fluorine Radioisotopes
  • Fluorobenzenes
  • Oligoribonucleotides
  • RNA, Double-Stranded
  • RNA, Small Interfering