Synthesis of an (Iodovinyl)misonidazole Derivative for Hypoxia Imaging

Joseph E. Biskupiak, John R. Grierson, Janet S. Rasey, Gary V. Martin, Kenneth A. Krohn

Research output: Contribution to journalArticlepeer-review

40 Scopus citations


Nitroimidazoles undergo a bioreduction in viable hypoxic tissue, resulting in trapping within these tissues, as demonstrated by misonidazole. A radioiodinated analogue of misonidazole (IVM, (E)-5-(2-Nitroimidazolyl)-4- hydroxy-1-iodopent-1-ene, 3) has been synthesized by halodestannylation, for evaluation as an imaging agent for hypoxia. A key step in the synthetic sequence involves the use of the Lewis acid BF3·Et2O to promote the nucleophilic ring opening of glycidyl tosylate with (E)-1-lithio-2-(tributylstannyl)ethylene. Direct comparison of IVM versus F-MISO (2) another misonidazole type hypoxic cell marker, in several in vitro cell culture studies, indicates that IVM behaves in analogous fashion to F-MISO and has promise as a hypoxia imaging agent for SPECT.

Original languageEnglish (US)
Pages (from-to)2165-2168
Number of pages4
JournalJournal of Medicinal Chemistry
Issue number7
StatePublished - Jul 1 1991
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery


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