L-364,373 (R-L3) enantiomers have opposite modulating effects on IKs in mammalian ventricular myocytes

Can J Physiol Pharmacol. 2013 Aug;91(8):586-92. doi: 10.1139/cjpp-2012-0407. Epub 2013 Jan 8.

Abstract

Activators of the slow delayed rectifier K⁺ current (IKs) have been suggested as promising tools for suppressing ventricular arrhythmias due to prolongation of repolarization. Recently, L-364,373 (R-L3) was nominated to activate IKs in myocytes from several species; however, in some studies, it failed to activate IKs. One later study suggested opposite modulating effects from the R-L3 enantiomers as a possible explanation for this discrepancy. Therefore, we analyzed the effect of the RL-3 enantiomers on IKs in ventricular mammalian myocytes, by applying standard microelectrode and whole-cell patch-clamp techniques at 37 °C. We synthesized 2 substances, ZS_1270B (right) and ZS_1271B (left), the 2 enantiomers of R-L3. In rabbit myocytes, ZS_1270B enhanced the IKs tail current by approximately 30%, whereas ZS_1271B reduced IKs tails by 45%. In guinea pig right ventricular preparations, ZS_1270B shortened APD90 (action potential duration measured at 90% repolarization) by 12%, whereas ZS_1271B lengthened it by approximately 15%. We concluded that R-L3 enantiomers in the same concentration range indeed have opposite modulating effects on IKs, which may explain why the racemic drug R-L3 previously failed to activate IKs. ZS_1270B is a potent IKs activator, therefore, this substance is appropriate to test whether IKs activators are ideal tools to suppress ventricular arrhythmias originating from prolongation of action potentials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Action Potentials / drug effects*
  • Animals
  • Benzodiazepines / chemical synthesis
  • Benzodiazepines / chemistry
  • Benzodiazepines / pharmacology*
  • Cells, Cultured
  • Delayed Rectifier Potassium Channels / agonists*
  • Delayed Rectifier Potassium Channels / antagonists & inhibitors*
  • Female
  • Guinea Pigs
  • Heart Ventricles / cytology
  • Heart Ventricles / drug effects*
  • Heart Ventricles / metabolism
  • Male
  • Microelectrodes
  • Molecular Structure
  • Myocytes, Cardiac / drug effects*
  • Myocytes, Cardiac / metabolism
  • Patch-Clamp Techniques
  • Rabbits
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Delayed Rectifier Potassium Channels
  • L 364373
  • Benzodiazepines