Potent Kv1.3 inhibitors from correolide-modification of the C18 position

Bioorg Med Chem Lett. 2005 Jan 17;15(2):447-51. doi: 10.1016/j.bmcl.2004.10.058.

Abstract

Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation.

MeSH terms

  • Biological Assay
  • Cell Proliferation / drug effects*
  • Humans
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / pharmacology
  • Ion Channel Gating / drug effects*
  • Kv1.3 Potassium Channel
  • Models, Molecular
  • Potassium Channel Blockers / chemistry
  • Potassium Channel Blockers / pharmacology*
  • Potassium Channels, Voltage-Gated / antagonists & inhibitors*
  • Structure-Activity Relationship
  • T-Lymphocytes
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*

Substances

  • Immunosuppressive Agents
  • KCNA3 protein, human
  • Kv1.3 Potassium Channel
  • Potassium Channel Blockers
  • Potassium Channels, Voltage-Gated
  • Triterpenes
  • correolide