Fast indirect fluorine-18 labeling of protein/peptide using the useful 6-fluoronicotinic acid-2,3,5,6-tetrafluorophenyl prosthetic group: A method comparable to direct fluorination

J Labelled Comp Radiopharm. 2017 Mar;60(3):168-175. doi: 10.1002/jlcr.3487. Epub 2017 Feb 1.

Abstract

Fluorine-18 labeling of biomolecules is mostly performed by an indirect labeling method using a prosthetic group. Fluorine-18 labeled 6-fluoronicotinic acid-2,3,5,6-tetrafluorophenyl ester is a useful prosthetic group to radiolabel a protein. Recently, we reported an improved preparation of this prosthetic group. To test the conjugation efficiency of the labeled ester prepared by this method, we have performed conjugation reactions with a peptide, a protein, and a small molecule. Prostate-specific membrane antigen targeting small molecule [18 F]DCFPyL, αvβ3 integrin receptors targeting peptide [18 F]c(RGDfK) and [18 F]albumin were prepared in good radiochemical yields. The conjugation reactions were completed at 40°C to 50°C in 10 minutes. The overall radiochemical yield was 25% to 43% in 30 to 45 minutes.

Keywords: F-18; peptide; protein; radiolabeling.

MeSH terms

  • Albumins / chemistry*
  • Amino Acid Sequence
  • Antigens, Surface / chemistry*
  • Fluorine Radioisotopes / chemistry*
  • Glutamate Carboxypeptidase II / chemistry*
  • Halogenation*
  • Isotope Labeling / methods*
  • Kinetics
  • Oligopeptides / chemistry*

Substances

  • Albumins
  • Antigens, Surface
  • Fluorine Radioisotopes
  • Oligopeptides
  • arginyl-glycyl-aspartic acid
  • FOLH1 protein, human
  • Glutamate Carboxypeptidase II
  • Fluorine-18