Synthesis of new carbon-11-labeled carboxamide derivatives as potential PET dopamine D3 receptor radioligands

Mingzhang Gao, Min Wang, Gary Hutchins, Qi-Huang Zheng

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Carbon-11-labeled carboxamide derivatives, (E)-4-fluoro-N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)cinnamoylamide, ([11C]3a), (E)-4-chloro-N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)cinnamoylamide ([11C]3b), (E)-4-bromo-N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)cinnamoylamide, ([11C]3c), (E)-4-methoxy-N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)cinnamoylamide ([11C]3d), N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)naphthyl-2-carboxamide ([11C]BP897, [11C]3e), and N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)biphenyl-4-carboxamide ([11C]3f), have been synthesized as new potential PET radioligands for imaging of dopamine D3 receptors. The target tracers were prepared by O-[11C]methylation of their corresponding precursors using [11C]CH3OTf and isolated by a simplified solid-phase extraction (SPE) purification procedure in 50-65% radiochemical yields decay corrected to end of bombardment (EOB), 20 min overall synthesis time, and 111-148 GBq/μmol specific activity at end of synthesis (EOS).

Original languageEnglish
Pages (from-to)1891-1897
Number of pages7
JournalApplied Radiation and Isotopes
Volume66
Issue number12
DOIs
StatePublished - Dec 2008

Fingerprint

dopamine
methylation
carbon
synthesis
purification
tracers
solid phases
bombardment
decay

Keywords

  • Carbon-11
  • Carboxamides
  • Dopamine D receptor
  • Imaging
  • Positron emission tomography (PET)

ASJC Scopus subject areas

  • Radiation

Cite this

Synthesis of new carbon-11-labeled carboxamide derivatives as potential PET dopamine D3 receptor radioligands. / Gao, Mingzhang; Wang, Min; Hutchins, Gary; Zheng, Qi-Huang.

In: Applied Radiation and Isotopes, Vol. 66, No. 12, 12.2008, p. 1891-1897.

Research output: Contribution to journalArticle

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AB - Carbon-11-labeled carboxamide derivatives, (E)-4-fluoro-N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)cinnamoylamide, ([11C]3a), (E)-4-chloro-N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)cinnamoylamide ([11C]3b), (E)-4-bromo-N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)cinnamoylamide, ([11C]3c), (E)-4-methoxy-N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)cinnamoylamide ([11C]3d), N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)naphthyl-2-carboxamide ([11C]BP897, [11C]3e), and N-(4-(4-(2-[11C]methoxyphenyl)piperazin-1-yl)butyl)biphenyl-4-carboxamide ([11C]3f), have been synthesized as new potential PET radioligands for imaging of dopamine D3 receptors. The target tracers were prepared by O-[11C]methylation of their corresponding precursors using [11C]CH3OTf and isolated by a simplified solid-phase extraction (SPE) purification procedure in 50-65% radiochemical yields decay corrected to end of bombardment (EOB), 20 min overall synthesis time, and 111-148 GBq/μmol specific activity at end of synthesis (EOS).

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KW - Dopamine D receptor

KW - Imaging

KW - Positron emission tomography (PET)

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