Synthesis of cyclopentadienyltricarbonyl rhenium phenyltropanes by double ligand transfer: organometallic ligands for the dopamine transporter
| Autor: | N. S. Kula, Ronald M. Baldwin, Gilles Tamagnan, Ross J. Baldessarini, Sami S. Zoghbi, Richard R. Cesati, John A. Katzenellenbogen, Robert B. Innis |
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| Rok vydání: | 2002 |
| Předmět: |
Perrhenate
Magnetic Resonance Spectroscopy Chemical Phenomena Stereochemistry Biomedical Engineering Pharmaceutical Science chemistry.chemical_element Bioengineering Nerve Tissue Proteins Ligands Binding Competitive chemistry.chemical_compound Mice Organometallic Compounds Animals Group 2 organometallic chemistry Dopamine transporter Pharmacology Dopamine Plasma Membrane Transport Proteins Membrane Glycoproteins biology Chemistry Ligand Chemistry Physical Organic Chemistry Membrane Transport Proteins Nuclear magnetic resonance spectroscopy Rhenium Neostriatum Kinetics Ferrocene Functional group biology.protein Indicators and Reagents Spectrophotometry Ultraviolet Chromatography Thin Layer Biotechnology Tropanes |
| Zdroj: | Bioconjugate chemistry. 13(1) |
| ISSN: | 1043-1802 |
| Popis: | 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 3 beta-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. |
| Databáze: | OpenAIRE |
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