A Rational Design of a Selective Inhibitor for Kv1.1 Channels Prevalent in Demyelinated Nerves That Improves Their Impaired Axonal Conduction

J Med Chem. 2017 Mar 23;60(6):2245-2256. doi: 10.1021/acs.jmedchem.6b01262. Epub 2017 Mar 13.

Abstract

K+ channels containing Kv1.1 α subunits, which become prevalent at internodes in demyelinated axons, may underlie their dysfunctional conduction akin to muscle weakness in multiple sclerosis. Small inhibitors were sought with selectivity for the culpable hyper-polarizing K+ currents. Modeling of interactions with the extracellular pore in a Kv1.1-deduced structure identified diaryldi(2-pyrrolyl)methane as a suitable scaffold with optimized alkyl ammonium side chains. The resultant synthesized candidate [2,2'-((5,5'(di-p-topyldiaryldi(2-pyrrolyl)methane)bis(2,2'carbonyl)bis(azanediyl)) diethaneamine·2HCl] (8) selectively blocked Kv1.1 channels (IC50 ≈ 15 μM) recombinantly expressed in mammalian cells, induced a positive shift in the voltage dependency of K+ current activation, and slowed its kinetics. It preferentially inhibited channels containing two or more Kv1.1 subunits regardless of their positioning in concatenated tetramers. In slices of corpus callosum from mice subjected to a demyelination protocol, this novel inhibitor improved neuronal conduction, highlighting its potential for alleviating symptoms in multiple sclerosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Corpus Callosum / drug effects
  • Corpus Callosum / metabolism
  • Corpus Callosum / pathology
  • Demyelinating Diseases / drug therapy
  • Demyelinating Diseases / metabolism
  • Demyelinating Diseases / pathology
  • Drug Design
  • Humans
  • Kv1.1 Potassium Channel / antagonists & inhibitors*
  • Kv1.1 Potassium Channel / metabolism
  • Male
  • Mice, Inbred C57BL
  • Molecular Docking Simulation
  • Potassium Channel Blockers / chemistry*
  • Potassium Channel Blockers / pharmacology*
  • Potassium Channel Blockers / therapeutic use
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • Pyrroles / therapeutic use

Substances

  • Potassium Channel Blockers
  • Pyrroles
  • Kv1.1 Potassium Channel