The use of [18F]4-fluorobenzyl iodide (FBI) in PET radiotracer synthesis: model alkylation studies and its application in the design of dopamine D1 and D2 receptor-based imaging agents

Nucl Med Biol. 1993 Aug;20(6):777-94. doi: 10.1016/0969-8051(93)90165-q.

Abstract

[18F]4-Fluorobenzyl iodide ([18F]FBI) was prepared, and a series of model alkylation studies were conducted to determine its chemical reactivity toward nitrogen and sulfur nucleophiles of varying nucleophilicities. [18F]FBI was found to react rapidly with secondary amines and anilines to give the corresponding N-[18F]4-fluorobenzyl analogue in high yield. Amides and thiol groups required the use of a base catalyst. The utility of [18F]FBI was documented by investigation of dopamine D1 and D2 receptor-based radiotracers.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkylation
  • Animals
  • Benzamides / chemical synthesis
  • Benzazepines / chemical synthesis
  • Fluorine Radioisotopes
  • Fluorobenzenes / chemical synthesis
  • Fluorobenzenes / chemistry*
  • Isotope Labeling / methods
  • Kinetics
  • Models, Chemical
  • Nitrogen / chemistry
  • Piperidines / chemical synthesis
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Dopamine D1 / analysis*
  • Receptors, Dopamine D1 / metabolism
  • Receptors, Dopamine D2 / analysis*
  • Receptors, Dopamine D2 / metabolism
  • Sulfur / chemistry
  • Tomography, Emission-Computed

Substances

  • Benzamides
  • Benzazepines
  • Fluorine Radioisotopes
  • Fluorobenzenes
  • Piperidines
  • Receptors, Dopamine D1
  • Receptors, Dopamine D2
  • fluoroclebopride
  • 7-chloro-8-hydroxy-1-(4'-(4-fluorobenzyl)thiophenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
  • 4-fluorobenzyl iodide
  • Sulfur
  • Nitrogen