Assessment of the pharmacological properties of 5-methoxyindole derivatives at 5-HT4 receptors

J Pharm Pharmacol. 2012 Aug;64(8):1099-106. doi: 10.1111/j.2042-7158.2012.01500.x. Epub 2012 Mar 16.

Abstract

Objectives: The aim was to examine the biological activity of 5-methoxytryptamine derivatives at the 5-hydroxytryptamine (5-HT)(4) receptor to explore the effect of substitution on the aliphatic amine of the 5-methoxyamine scaffold.

Methods: Three compounds were tested for affinity at the 5-HT(4) receptor by radioligand binding and functional activity using guinea-pig ileum and human colon circular muscle preparations and also in the mouse whole gut transit test.

Key findings: The three compounds all had agonist properties at the 5-HT(4) receptor but their efficacy differed in the different functional tests. Compound 3 had the highest affinity for the 5-HT(4) receptor and was a full agonist at relaxing human colon circular muscle with efficacy closest to 5-HT. Compounds 1 and 2 were partial agonists in this assay with lower efficacies; compound 2 was a full agonist in the guinea-pig ileum assay whereas compound 3 was a partial agonist. Compounds 1 and 2 also showed activity in the mouse gut transit assay while compound 3 had no activity.

Conclusions: Of the compounds tested, compound 3 was the most promising 5-HT(4) receptor agonist and the results highlight the value of using human tissue in functional tests when assessing compounds for potential activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 5-Methoxytryptamine / analogs & derivatives
  • 5-Methoxytryptamine / pharmacology*
  • Animals
  • Colon / drug effects*
  • Female
  • Gastrointestinal Transit / drug effects
  • Guinea Pigs
  • Humans
  • Hydroxylamines / pharmacology
  • Ileum / drug effects*
  • Indoles / pharmacology*
  • Mice
  • Mice, Inbred Strains
  • Muscle Contraction / drug effects*
  • Muscle, Smooth / drug effects*
  • Receptors, Serotonin, 5-HT4 / metabolism*

Substances

  • Hydroxylamines
  • Indoles
  • Receptors, Serotonin, 5-HT4
  • 5-Methoxytryptamine
  • methoxyamine
  • 5-methoxyindole