Tos-Nos-Mos: Synthesis of different aryl sulfonate precursors for the radiosynthesis of the alpha7 nicotinic acetylcholine receptor radioligand [(18)F]NS14490

Appl Radiat Isot. 2016 Aug:114:57-62. doi: 10.1016/j.apradiso.2016.04.028. Epub 2016 Apr 28.

Abstract

Radiopharmacological investigations of [(18)F]NS14490 have proven that this radiotracer could be a potential PET radiotracer for imaging of alpha7 nicotinic acetylcholine receptor particularly with regard to vulnerable plaques of diseased vessels. For further optimisation of the previously automated one-pot radiosynthesis of [(18)F]NS14490 using a tosylate precursor, precursors with other leaving groups (nosylate and mosylate) were synthesized and compared with the tosylate with respect to their reactivities towards [(18)F]fluoride. The use of these different precursors resulted in comparable labelling yields of [(18)F]NS14490. A novel mosylate precursor was synthesized and evaluated, which has revealed a higher stability during a storage period of five months compared to the corresponding tosylate and nosylate.

Keywords: Alpha7 nAChR ligand; Mosylate; Nosylate; PET; Reactivity of precursor; Synthesis of precursor; Tosylate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arylsulfonates / chemistry
  • Benzenesulfonates / chemical synthesis
  • Benzenesulfonates / chemistry
  • Drug Stability
  • Fluorine Radioisotopes / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacokinetics
  • Molecular Imaging
  • Molecular Structure
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacokinetics
  • Positron-Emission Tomography
  • Radioligand Assay
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacokinetics
  • Tosyl Compounds / chemical synthesis
  • Tosyl Compounds / chemistry
  • alpha7 Nicotinic Acetylcholine Receptor / metabolism*

Substances

  • Arylsulfonates
  • Benzenesulfonates
  • Fluorine Radioisotopes
  • Indoles
  • NS14490
  • Oxadiazoles
  • Radiopharmaceuticals
  • Tosyl Compounds
  • alpha7 Nicotinic Acetylcholine Receptor