TMSOTf assisted synthesis of 2'-deoxy-2'-[18F]fluoro-β-D-arabinofuranosylcytosine ([18F]FAC). Academic Article uri icon

Overview

abstract

  • [18F]FAC (2'-deoxy-2'-[18F]fluoro-β-D-arabinofuranosylcytosine, 1) is a versatile probe for imaging deoxycytidine kinase (dCK) expression levels in vivo. dCK is responsible for phosphorylation of deoxycytidine (dC, 2) and other nucleoside analogs, plays a key role in immune activation and has demonstrated to be one of the key enzymes in activating nucleoside based drugs including gemcitabine. Reported synthesis of [18F]FAC is high yielding but is quite challenging requiring bromination using HBr and careful drying of excess HBr which is critical for successful synthesis. Here in we report a simplified trimethylsilyl trifluoromethanesulfonate (TMSOTf) assisted synthesis of [18F]FAC eliminating the need of bromination and drying. [18F]FAC (β-anomer) was synthesized with average isolated decay corrected yield of 10.59 + 4.2% (n = 6) with radiochemical purity of >98% and total synthesis time of 158 + 19 min.

publication date

  • May 1, 2018

Research

keywords

  • Cytarabine
  • Fluorine Radioisotopes
  • Mesylates
  • Radiopharmaceuticals
  • Trimethylsilyl Compounds

Identity

PubMed Central ID

  • PMC5929562

Scopus Document Identifier

  • 85046254966

Digital Object Identifier (DOI)

  • 10.1007/s00259-006-0305-1

PubMed ID

  • 29715301

Additional Document Info

volume

  • 13

issue

  • 5