18F-labeling using click cycloadditions

Biomed Res Int. 2014:2014:361329. doi: 10.1155/2014/361329. Epub 2014 May 27.

Abstract

Due to expanding applications of positron emission tomography (PET) there is a demand for developing new techniques to introduce fluorine-18 (t 1/2 = 109.8 min). Considering that most novel PET tracers are sensitive biomolecules and that direct introduction of fluorine-18 often needs harsh conditions, the insertion of (18)F in those molecules poses an exceeding challenge. Two major challenges during (18)F-labeling are a regioselective introduction and a fast and high yielding way under mild conditions. Furthermore, attention has to be paid to functionalities, which are usually present in complex structures of the target molecule. The Cu-catalyzed azide-alkyne cycloaddition (CuAAC) and several copper-free click reactions represent such methods for radiolabeling of sensitive molecules under the above-mentioned criteria. This minireview will provide a quick overview about the development of novel (18)F-labeled prosthetic groups for click cycloadditions and will summarize recent trends in copper-catalyzed and copper-free click (18)F-cycloadditions.

Publication types

  • Review

MeSH terms

  • Animals
  • Catalysis
  • Click Chemistry / methods*
  • Copper / chemistry
  • Cycloaddition Reaction*
  • Fluorine Radioisotopes / chemistry*
  • Staining and Labeling*

Substances

  • Fluorine Radioisotopes
  • Copper