Synthesis of cyclopentadienyltricarbonyl rhenium phenyltropanes by double ligand transfer: Organometallic ligands for the dopamine transporter

Richard R. Cesati, Gilles Tamagnan, Ronald M. Baldwin, Sami S. Zoghbi, Robert B. Innis, Nora S. Kula, Ross J. Baldessarini, John A. Katzenellenbogen

Research output: Contribution to journalArticlepeer-review

Abstract

Cyclopentadienyltricarbonyl rhenium (CpRe(CO)3) systems can be prepared from ferrocenes and perrhenate by a double ligand transfer (DLT) reaction that gives reasonable yields and shows excellent functional group tolerance. We used this reaction for the direct preparation of CpRe(CO)3-phenyltropane conjugates. Such agents, when labeled with technetium-99m, might function as imaging agents for the dopamine transporter (DAT) system that would be useful for assessing the onset and severity of Parkinson's disease. Of the CpRe(CO)3-tropane conjugates prepared by the DLT reaction (as well as other analogues prepared by related methods), those substituted at the N-8 position seem most promising; their affinity for the DAT in all cases was high, and their ferrocene precursors for the DLT reaction can be prepared in a convenient manner. By contrast, the 3β-conjugates were poor DAT binders. The modular nature of these systems offers considerable flexibility that could be used to improve the binding characteristics of these compounds further.

Original languageEnglish (US)
Pages (from-to)29-39
Number of pages11
JournalBioconjugate Chemistry
Volume13
Issue number1
DOIs
StatePublished - 2002

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

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