Fully automated synthesis of [<sup>18</sup>F]T807, a PET tau tracer for Alzheimer's disease

Mingzhang Gao, Min Wang, Qi-Huang Zheng

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The authentic standard T807 and its nitro-precursor T807P as well as t-Boc-protected T807P precursor for radiolabeling were synthesized from (4-bromophenyl)boronic acid, 3-bromo-4-nitropyridine and 3-bromo-6-nitropyridine with overall chemical yield 27% in three steps, 4-7% in three to five steps, and 3-8% in four to five steps, respectively. [<sup>18</sup>F]T807 was synthesized from T807P by the nucleophilic [<sup>18</sup>F]fluorination with K[<sup>18</sup>F]F/Kryptofix 2.2.2 in DMSO at 140 °C followed by reduction with Fe powder/HCOOH through manual synthesis with 5-10% decay corrected radiochemical yield in two steps. [<sup>18</sup>F]T807 was also synthesized from t-Boc-protected T807P by a concurrent [<sup>18</sup>F]fluorination and deprotection with K[<sup>18</sup>F]F/Kryptofix 2.2.2 in DMSO at 140 °C and purified by HPLC-SPE method in a home-built automated [<sup>18</sup>F]radiosynthesis module with 20-30% decay corrected radiochemical yield in one step. The specific activity of [<sup>18</sup>F]T807 at end of bombardment (EOB) was 37-370 GBq/μmol.

Original languageEnglish
Pages (from-to)2953-2957
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number15
DOIs
StatePublished - Apr 24 2015

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Fluorination
Halogenation
Dimethyl Sulfoxide
Alzheimer Disease
Powders
High Pressure Liquid Chromatography
4-nitropyridine
4-bromophenylboric acid

Keywords

  • Alzheimer's disease (AD)
  • Automation
  • Positron emission tomography (PET)
  • Tau tracer
  • [<sup>18</sup>F]T807

ASJC Scopus subject areas

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

Cite this

Fully automated synthesis of [<sup>18</sup>F]T807, a PET tau tracer for Alzheimer's disease. / Gao, Mingzhang; Wang, Min; Zheng, Qi-Huang.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 25, No. 15, 24.04.2015, p. 2953-2957.

Research output: Contribution to journalArticle

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