Radiosynthesis of new carbon-11-labeled nimesulide analogs as potential PET SAER tracers for imaging of aromatase expression in breast cancer

Min Wang, Mingzhang Gao, Kathy D. Miller, George W. Sledge, Gary D. Hutchins, Qi Huang Zheng

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

Carbon-11-labeled nimesulide analogs, N-[11C]methyl-N-(2- benzyloxy-4-nitrophenyl)methanesulfonamide ([11C]4a), N-[ 11C]methyl-N-[2-(4'-methylbenzyloxy)-4-nitrophenyl] methanesulfonamide ([11C]4b), N-[11C]methyl-N-[2-(4'- fluorobenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]4c), N-[ 11C]methyl-N-[2-(4'-nitrobenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]8a), N-[11C]methyl-N-[2-(-naphthylmethoxy)-4- nitrophenyl]methanesulfonamide ([11C]8b), and N-[11C] methyl-N-[2-(2'-phenylbenzyloxy)-4-nitrophenyl]methanesulfonamide ([ 11C]8c), have been synthesized as new potential positron emission tomography (PET) selective aromatase expression regulator (SAER) radiotracers for imaging of aromatase expression in breast cancer. The target tracers were prepared by N-[11C]methylation of their corresponding precursors using [11C]CH3OTf under basic conditions (NaH) and isolated by reversed-phase high-pressure liquid chromatography (HPLC) method in 30-50% radiochemical yields decay corrected to end of bombardment (EOB) with 25-30min overall synthesis time and 111-148 GBq/mol specific activity at end of synthesis (EOS).

Original languageEnglish (US)
Pages (from-to)749-758
Number of pages10
JournalSynthetic Communications
Volume40
Issue number5
DOIs
StatePublished - Jan 2010

Keywords

  • Aromatase expression
  • Breast cancer
  • Imaging
  • Nimesulides
  • Positron emission tomography (PET)
  • Radiosynthesis

ASJC Scopus subject areas

  • Organic Chemistry

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