Synthesis and preliminary in vitro biological evaluation of new carbon-11-labeled celecoxib derivatives as candidate PET tracers for imaging of COX-2 expression in cancer

Mingzhang Gao, Min Wang, Kathy D. Miller, Qi Huang Zheng

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17 Scopus citations


The enzyme cyclooxygenase-2 (COX-2) is overexpressed in a variety of malignant tumors. This study was designed to develop new radiotracers for imaging of COX-2 in cancer using biomedical imaging technique positron emission tomography (PET). Carbon-11-labeled celecoxib derivatives, [ 11C]4a-c and [ 11C]8a-d, were prepared by O-[ 11C] methylation of their corresponding precursors using [ 11C]CH 3OTf under basic conditions and isolated by a simplified solid-phase extraction (SPE) method in 52 ± 2% (n = 5) and 57 ± 3% (n = 5) radiochemical yields based on [ 11C]CO 2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 277.5 ± 92.5 GBq/μmol (n = 5). The IC 50 values to block COX-2 for known compounds celecoxib (4d), 4a and 4c were 40, 290 and 8 nM, respectively, and preliminary findings from in vitro biological assay indicated that the synthesized new compounds 4b and 8a-d display similar strong inhibitory effectiveness in the MDA-MB-435 human cancer cell line in comparison with the parent compound 4d. These results encourage further in vivo evaluation of carbon-11-labeled celecoxib derivatives as new potential PET radiotracers for imaging of COX-2 expression in cancer.

Original languageEnglish (US)
Pages (from-to)4760-4767
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Issue number9
StatePublished - Sep 1 2011



  • Cancer imaging
  • Carbon-11-labeled celecoxib derivatives
  • Cyclooxygenase-2 (COX-2)
  • Positron emission tomography (PET)
  • Radiotracers

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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