Stoichiometry-focused (18)F-labeling of alkyne-substituted oligodeoxynucleotides using azido([(18)F]fluoromethyl)benzenes by Cu-catalyzed Huisgen reaction

Bioorg Med Chem. 2011 Jan 1;19(1):249-55. doi: 10.1016/j.bmc.2010.11.033. Epub 2010 Nov 19.

Abstract

A novel method for (18)F-radiolabeling of oligodeoxynucleotides (ODNs) by a Cu-catalyzed Huisgen reaction has been developed by using the lowest possible amount of the precursor biomolecule for the realization of stoichiometry-oriented PET (positron emission tomography) chemistry. Under the optimized cyclization conditions of p- or m-azido([(18)F]fluoromethyl)benzene and alkyne-substituted ODN (20nmol) at 40°C for 15min in the presence of CuSO(4), TBTA [tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine], and sodium ascorbate (2:1:2), the synthesis of (18)F-labeled ODNs with sufficiently high radioactivities of 2.1-2.5GBq and specific radioactivities of 1800-2400GBq/μmol have been accomplished for use in animal and human PET studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzene Derivatives / chemistry*
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Copper / chemistry*
  • Fluorine Radioisotopes / chemistry*
  • Humans
  • Male
  • Oligodeoxyribonucleotides / chemistry*
  • Positron-Emission Tomography
  • Rats
  • Rats, Sprague-Dawley
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Benzene Derivatives
  • Fluorine Radioisotopes
  • Oligodeoxyribonucleotides
  • Copper