Pharmacological characterization of (E)-N-(3-iodoprop-2-enyl)-2beta-carbomethoxy-3beta-(4'-methylphenyl)n ortropane as a selective and potent inhibitor of the neuronal dopamine transporter

J Pharmacol Exp Ther. 1999 Nov;291(2):648-54.

Abstract

The pharmacological properties of the iodinated derivative of cocaine (E)-N-(3-iodoprop-2-enyl)-2beta-carbomethoxy-3beta-(4'-me thylphenyl)nortropane (PE2I) were evaluated in vitro in the rat. Binding experiments on rat striatal membranes showed that PE2I selectively recognized the dopamine transporter (DAT) according to a single binding site model with high affinity (K(d) = 4 nM, B(max) = 12 pmol/mg protein). In the cortical membranes, the binding of PE2I was also selectively associated with the DAT (IC(50) for GBR 12909 = 6 nM versus more than 1000 nM for paroxetine), with similar affinity to that of the striatum. Autoradiographic experiments on rat brain sections with [(125)I]PE2I were in agreement with the localization of the DAT. In addition, PE2I was shown to be a potent inhibitor of dopamine uptake, with IC(50) values similar to those for GBR 12909 and 2beta-carbomethoxy-3beta-(4'-iodophenyl)-tropane (beta-CIT) (2-6 nM). All of these findings, combined with previously published data, support the use of PE2I as a selective and potent tool to study the DAT both in vivo and in vitro.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Autoradiography
  • Biological Transport, Active / drug effects
  • Cocaine / analogs & derivatives
  • Cocaine / pharmacology
  • Dopamine / pharmacokinetics*
  • Dopamine Uptake Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • In Vitro Techniques
  • Male
  • Nortropanes / pharmacology*
  • Piperazines / pharmacology
  • Protein Binding
  • Radiopharmaceuticals / pharmacology*
  • Rats
  • Rats, Wistar
  • Visual Cortex / metabolism*

Substances

  • Dopamine Uptake Inhibitors
  • N-(3-iodoprop-2-enyl)-2-beta-carbomethoxy-3-(4-methylphenyl)nortropane
  • Nortropanes
  • Piperazines
  • Radiopharmaceuticals
  • 2beta-carbomethoxy-3beta-(4-iodophenyl)tropane
  • vanoxerine
  • Cocaine
  • Dopamine