Novel rhenium complexes derived from alpha-tropanol as potential ligands for the dopamine transporter

Bioorg Med Chem. 1998 Oct;6(10):1663-72. doi: 10.1016/s0968-0896(98)00144-8.

Abstract

A series of rhenium complexes was synthesized as model compounds for the corresponding radioactive technetium-99m complexes for preliminary biological investigations. In a '3 + 1' mixed-ligand approach the tropanol molecule was linked with the metal core through a omega-mercaptoester group as monodentate ligand. Bis(thioethyl)sulphide was used as the tridentate dithiol ligand to block the remaining free coordination sites. The omega-mercaptoesters were synthesized via the trityl-protected precursors. Binding tests on the cloned human dopamine transporter revealed moderate binding affinities for some of the prepared compounds. The complexes were characterised by X-ray and the lipophilicity as well as pKa values were determined.

Publication types

  • Comparative Study

MeSH terms

  • Carrier Proteins / metabolism*
  • Chromatography, High Pressure Liquid
  • Cocaine / analogs & derivatives
  • Cocaine / metabolism
  • Crystallography, X-Ray
  • Dopamine Plasma Membrane Transport Proteins
  • Humans
  • Membrane Glycoproteins*
  • Membrane Transport Proteins*
  • Nerve Tissue Proteins*
  • Piperazines / metabolism
  • Rhenium / chemistry*
  • Structure-Activity Relationship
  • Tropanes / chemistry*
  • Tropanes / metabolism*

Substances

  • Carrier Proteins
  • Dopamine Plasma Membrane Transport Proteins
  • Membrane Glycoproteins
  • Membrane Transport Proteins
  • Nerve Tissue Proteins
  • Piperazines
  • Tropanes
  • (1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
  • Rhenium
  • vanoxerine
  • Cocaine