Synthesis of novel progestin-rhenium conjugates as potential ligands for the progesterone receptor

F. Wüst, M. B. Skaddan, P. Leibnitz, H. Spies, J. A. Katzenellenbogen, B. Johannsen

Research output: Contribution to journalArticlepeer-review


To assist in the development of technetium-based radiopharmaceuticals that are useful for the diagnostic imaging of steroid receptor-positive breast tumors, we have synthesized a series of small-sized metal chelates according to 'n+1' mixed-ligand, thioether-carbonyl and organometallic designs. In these preliminary investigations, rhenium was used as a model for the radioactive technetium. The metal chelates contain the rhenium metal in several oxidation states, being +5, +3, and +1, and they were attached to 21-substituted progesterone derivatives. A competitive receptor-binding assay (rat uterine cytosol, 0°C) was used to determine the binding affinity of these conjugates for the progesterone receptor. The highest affinity of 9% (RU5020=100%) was obtained with a '3+1' mixed-ligand complex, containing a NMe group as the central donor atom in the tridentate ligand part. This value reflects a relative binding affinity of 75% compared with the parent steroid progesterone.

Original languageEnglish (US)
Pages (from-to)1827-1835
Number of pages9
JournalBioorganic and Medicinal Chemistry
Issue number9
StatePublished - Sep 1999


  • 21-Substituted progesterone
  • Progesterone receptor
  • Relative binding affinities
  • Rhenium

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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