Analysis of 3-(4-hydroxy, 2-Methoxybenzylidene)anabaseine selectivity and activity at human and rat alpha-7 nicotinic receptors

J Pharmacol Exp Ther. 1998 Dec;287(3):918-25.

Abstract

3-(2,4-dimethoxybenzylidene)anabaseine (GTS-21) is a selective partial agonist for rat alpha-7 nicotine receptors with reportedly much lower efficacy for human alpha-7 receptors. Because this drug improves memory-related performance in nonhuman primates, and is presently in a clinical trial for Alzheimer's disease, we investigated the potential effects of its primary human metabolite, 3-(4-hydroxy, 2-methoxy-benzylidene)anabaseine) on human as well as rat nicotinic acetylcholine receptor. 4OH-GTS-21 exhibited a similar level of efficacy for both rat and human alpha-7 receptors expressed in Xenopus oocytes. It displaced high affinity [125I]alpha-bungarotoxin binding to human SK-N-SH cell-membranes (Ki 0.17 microM) and rat PC12 cell-membranes (Ki 0.45 microM). GTS-21 also displaced [125I]alpha-bungarotoxin binding to PC12 cell membranes with high potency (Ki 0.31 microM), but was much less potent in this regard in SK-N-SH cells (23 microM). 4OH-GTS-21 produced less residual inhibition of either the human or rat AChR subtypes than GTS-21 did. To compare the neuroprotective efficacies of GTS-21 and 4OH-GTS-21 in both species, an amyloid-toxicity model (Abeta 25-35) was used. 4OH-GTS-21 was protective in both human and rat cell lines, although GTS-21 was effective only in the latter. These studies suggest that the efficacy of GTS-21 in primates may depend on a pro-drug function.

Publication types

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

MeSH terms

  • Anabasine / analogs & derivatives*
  • Anabasine / pharmacology
  • Animals
  • Benzylidene Compounds / metabolism
  • Benzylidene Compounds / pharmacology
  • Bungarotoxins / metabolism
  • Cloning, Molecular
  • Dose-Response Relationship, Drug
  • Humans
  • Nicotinic Agonists / metabolism
  • Nicotinic Agonists / pharmacology*
  • Oocytes / metabolism
  • PC12 Cells
  • Pyridines / metabolism
  • Pyridines / pharmacology
  • Rats
  • Receptors, Nicotinic / drug effects*
  • Receptors, Nicotinic / genetics
  • Receptors, Nicotinic / metabolism
  • Species Specificity
  • Xenopus laevis
  • alpha7 Nicotinic Acetylcholine Receptor

Substances

  • 3-(4-hydroxy-2-methoxybenzylidene)anabaseine
  • Benzylidene Compounds
  • Bungarotoxins
  • Chrna7 protein, human
  • Chrna7 protein, rat
  • Nicotinic Agonists
  • Pyridines
  • Receptors, Nicotinic
  • alpha7 Nicotinic Acetylcholine Receptor
  • 3-(2,4-dimethoxybenzylidene)anabaseine
  • Anabasine