Design and synthesis of [125I]Pyricoxib: a novel 125I-labeled cyclooxygenase-2 (COX-2) inhibitors

Ole Tietz, James Dzandzi, Atul Bhardwaj, John F. Valliant, Frank Wuest*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)


Cyclooxygenase-2 (COX-2) is the key enzyme in the prostaglandin synthesis pathway which is involved in various pathophysiological conditions. The enzyme is membrane bound and located inside of the endoplasmic reticulum and nuclear membrane. Effective perfusion of inhibitors to the active site requires lipophilic drugs, which consequently display high unspecific background accumulation, for example, in fatty tissues. The objective of this work was the development of a small molecule radiolabeled with a long-lived iodine radioisotope to enable longer imaging times and better target-to-background ratios. A group of iodinated compounds (8–10) was synthesized and identified as selective COX-2 inhibitors (COX-2 IC50 = 0.85–13 μM). Molecular docking results provided the theoretical support for the experimental COX-2 inhibition data. Furthermore, a novel125I-containing trifluoro-pyrimidine compound ([125I]Pyricoxib) was prepared via radioiododestannylation reaction as potent and selective COX-2 inhibitor. Radiosynthesis of [125I]Pyricoxib was accomplished with innovative fluorous chemistry using fluorous chloroamine-T (F-CAT) as novel oxidizing agent in high radiochemical yields of 91 ± 4%.

Original languageEnglish
Pages (from-to)1516-1520
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Issue number6
Publication statusPublished - 15 Mar 2016
Externally publishedYes


  • Cyclooxygenase-2
  • Fluorous chemistry
  • Iodine-125


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