Characterization of (125)I-IABN, a novel azabicyclononane benzamide selective for D2-like dopamine receptors

Synapse. 2000 Dec 15;38(4):438-49. doi: 10.1002/1098-2396(20001215)38:4<438::AID-SYN9>3.0.CO;2-5.

Abstract

The properties of an (125)I-labeled structural analog of 2, 3-dimethoxy-N-[9-(4-fluorobenzyl)-9-azabicyclo[3.3. 1]nonan-3beta-yl]benzamide (MABN), (125)I-IABN, are described. (125)I-IABN was developed as a high-affinity radioligand selective for the D2-like (D2, D3, and D4) dopamine receptor subtypes. (125)I-IABN binds with picomolar affinity and nonselectively to rat D2 and D3 dopamine receptors expressed in Sf9 and HEK 293 cells. (125)I-IABN binds with 7- to 25-fold lower affinity to human D4.4 dopamine receptors expressed in HEK 293 cells. Dissociation constants (Kd) calculated from kinetic experiments were in agreement with equilibrium Kd values obtained from saturation binding studies. Saturation plots of the binding of (125)I-IABN with rat caudate membrane preparations were monophasic and exhibited low nonspecific binding. The pharmacologic profile of the binding of (125)I-IABN to rat caudate was consistent with a D2-like receptor, suggesting that the ligand binds primarily to D2 dopamine receptors. In addition, IABN was found to bind with low affinity to D1 dopamine receptors, as well as to the sigma1 and sigma2 receptor subtypes. Quantitative autoradiographic studies using rat brain slices indicate that (125)I-IABN selectively labels the striatum and the olfactory tubercle area, which is consistent with the labeling of D2-like receptors. IABN blocks dopamine-dependent inhibition of adenylyl cyclase activity at D2 or D4.4 receptors expressed in HEK cells. Therefore, (125)I-IABN appears to be a high-affinity, selective antagonist at D2-like dopamine receptors. Finally, a unique property of the azabicyclononane benzamide (125)I-IABN compared to previously studied substituted benzamides is that the binding of this radioligand is not effected by variations in Na(+) concentration.

MeSH terms

  • Animals
  • Autoradiography
  • Benzamides / metabolism*
  • Bridged Bicyclo Compounds, Heterocyclic / metabolism*
  • Caudate Nucleus / metabolism
  • Cell Line
  • Humans
  • In Vitro Techniques
  • Insecta
  • Iodine Radioisotopes
  • Kinetics
  • Membranes / metabolism
  • Radioligand Assay
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Dopamine D2 / biosynthesis
  • Receptors, Dopamine D2 / isolation & purification
  • Receptors, Dopamine D2 / metabolism*

Substances

  • Benzamides
  • Bridged Bicyclo Compounds, Heterocyclic
  • Iodine Radioisotopes
  • Receptors, Dopamine D2
  • 2,3-dimethoxy-N-(9-(4-fluorobenzyl)-9-azabicyclo(3.3.1)nonan-3-yl)benzamide