Synthesis of a PET tau tracer [11C]PBB3 for imaging of Alzheimer's disease

Min Wang, Mingzhang Gao, Zhidong Xu, Qi-Huang Zheng

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from 5-bromo-2-nitropyridine, acrolein diethyl acetal, 6-methoxy-2-methylbenzothiazole, and diethylchlorophosphate with overall chemical yield 1% in six steps, 2% in five steps, and 1% in six steps, respectively. [11C]PBB3 was prepared from either desmethyl-PBB3 or TBS-protected desmethyl-PBB3 with [11C]CH3OTf through N-[11C]methylation and isolated by HPLC combined with SPE in 20-25% and 15-20% radiochemical yield, respectively, based on [11C]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was >99%, and the specific activity at EOB was 370-1110 GBq/μmol with a total synthesis time of ∼40-min from EOB.

Original languageEnglish
Pages (from-to)4587-4592
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number20
DOIs
StatePublished - Jul 29 2015

Fingerprint

Methylation
Alzheimer Disease
Imaging techniques
High Pressure Liquid Chromatography
diethylchlorophosphate
acrolein diethylacetal
2-(4-(6-(methylamino)pyridin-3-yl)buta-1,3-dienyl)benzo(d)thiazol-6-ol
5-bromo-2-nitropyridine

Keywords

  • Alzheimer's disease (AD)
  • Positron emission tomography (PET)
  • Radiosynthesis
  • Tau tracer
  • [C]PBB3

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Synthesis of a PET tau tracer [11C]PBB3 for imaging of Alzheimer's disease. / Wang, Min; Gao, Mingzhang; Xu, Zhidong; Zheng, Qi-Huang.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 25, No. 20, 29.07.2015, p. 4587-4592.

Research output: Contribution to journalArticle

Wang, Min ; Gao, Mingzhang ; Xu, Zhidong ; Zheng, Qi-Huang. / Synthesis of a PET tau tracer [11C]PBB3 for imaging of Alzheimer's disease. In: Bioorganic and Medicinal Chemistry Letters. 2015 ; Vol. 25, No. 20. pp. 4587-4592.
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