Labeling proteins with fluorine-18 using N-succinimidyl 4-[18F]fluorobenzoate

Int J Rad Appl Instrum B. 1992 Apr;19(3):275-81. doi: 10.1016/0883-2897(92)90111-b.


Two methods were investigated for the no-carrier-added synthesis of N-succinimidyl 4-[18F]fluorobenzoate (S[18F]FB). The first, an attempted nucleophilic aromatic substitution by [18F]fluoride on N-succinimidyl 4-nitrobenzoate was unsuccessful. The second method involved three steps; [18F]fluoride for trimethylammonium substitution on 4-formyl-N,N,N-trimethylanilinium triflate, oxidation to 4-[18F]fluorobenzoic acid, followed by reaction with N-hydroxysuccinimide and dicyclohexylcarbodiimide to form S[18F]FB. Total synthesis and purification time was 100 min and the overall radiochemical yield was 25% (decay corrected). A monoclonal antibody F(ab')2 fragment could be labeled in 40-60% yield by reaction with S[18F]FB for 15-20 min. The tissue distribution in normal mice and in vitro tumor binding of the antibody F(ab')2 labeled by reaction with S[18F]FB were comparable to those observed for the fragment after radioiodination using N-succinimidyl 4-[125I]iodobenzoate.

Publication types

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

MeSH terms

  • Animals
  • Antibodies, Monoclonal / immunology
  • Antibodies, Monoclonal / metabolism
  • Benzoates / chemical synthesis*
  • Fluorine Radioisotopes*
  • Half-Life
  • Immunoglobulin Fragments / immunology
  • Immunoglobulin Fragments / metabolism
  • Isotope Labeling / methods
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Proteins / chemistry*
  • Succinimides / chemical synthesis*
  • Tissue Distribution


  • Antibodies, Monoclonal
  • Benzoates
  • Fluorine Radioisotopes
  • Immunoglobulin Fragments
  • Proteins
  • Succinimides
  • N-succinimidyl-4-fluorobenzoate