An in situ oxidation strategy towards overcoming hERG affinity

Bioorg Med Chem Lett. 2010 Nov 15;20(22):6400-4. doi: 10.1016/j.bmcl.2010.09.089. Epub 2010 Sep 21.

Abstract

In an effort to overcome hERG affinity with a lead compound, several S-oxide and N-oxide analogues were synthesised with a much improved hERG profile but low in vivo absorption. This led to the implementation of an in situ oxidation strategy wherein a sulfide was dosed orally and systemic levels of the corresponding sulfoxide and sulfone were monitored. SAR and pharmacokinetic data to support this as a possible strategy are presented, although ultimately the approach was shown not to be suitable due to very low levels of active circulating metabolites.

MeSH terms

  • Animals
  • Area Under Curve
  • Biological Availability
  • Chromatography, High Pressure Liquid
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels / drug effects*
  • Ether-A-Go-Go Potassium Channels / metabolism
  • Oxidation-Reduction
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfides / metabolism
  • Sulfides / pharmacokinetics
  • Sulfides / pharmacology*

Substances

  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels
  • Sulfides