Efficient radiosynthesis of carbon-11 labelled uncharged Thioflavin T derivatives using [11C]methyl triflate for beta-amyloid imaging in Alzheimer's Disease with PET

Appl Radiat Isot. 2005 Apr;62(4):591-5. doi: 10.1016/j.apradiso.2004.09.003.

Abstract

The synthesis of carbon-11 amino function labelled uncharged Thioflavin T derivatives is known to be performed by reaction of the demethyl-precursors with [11C]methyl iodide but the labelling yields are only mediocre. The use of [11C]methyl triflate improved the radiochemical yield of three potential beta-amyloid imaging PET-radiotracers significantly. Performance of the labelling reaction by reacting the corresponding precursor molecules with [11C]methyl triflate for 1 min at 80 degrees C led to radiochemical yields of 44+/-10% (n=5) for [11C]6-Me-BTA-1, 68+/-4% (n=10) for [11C]BTA-1 and 58+/-2% (n=5) for [11C]6-OH-BTA-1 with respect to [11C]methyl triflate. In production runs (60 min, 50 microA) up to 6500 MBq (mean: 4000+/-1900 MBq) of [11C]6-Me-BTA-1, 7900 MBq (mean: 6000+/-1000 MBq) of [11C]BTA-1 and 7100 MBq (mean: 6300+/-600 MBq) of [11C]6-OH-BTA-1 could be obtained ready for intravenous injection. The radiochemical purity was >95% with specific activities in the range of 80-120 GBq/micromol (EOS) within a total synthesis time of less than 40 min after EOB.

MeSH terms

  • Alzheimer Disease / diagnostic imaging*
  • Amyloid beta-Peptides / analysis
  • Aniline Compounds / chemical synthesis
  • Aniline Compounds / chemistry*
  • Benzothiazoles
  • Carbon Radioisotopes / chemistry*
  • Humans
  • Isotope Labeling / methods
  • Mesylates / chemical synthesis
  • Mesylates / chemistry*
  • Positron-Emission Tomography / methods*
  • Radiopharmaceuticals / chemical synthesis*
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry*

Substances

  • 2-(4'-methylaminophenyl)benzothiazole
  • Amyloid beta-Peptides
  • Aniline Compounds
  • Benzothiazoles
  • Carbon Radioisotopes
  • Mesylates
  • Radiopharmaceuticals
  • Thiazoles
  • thioflavin T
  • trifluoromethanesulfonic acid