Nicotinic acids: liver-targeted SCD inhibitors with preclinical anti-diabetic efficacy

Bioorg Med Chem Lett. 2011 Dec 15;21(24):7281-6. doi: 10.1016/j.bmcl.2011.10.040. Epub 2011 Oct 18.

Abstract

An in vitro screening protocol was used to transform a systemically-distributed SCD inhibitor into a liver-targeted compound. Incorporation of a key nicotinic acid moiety enables molecular recognition by OATP transporters, as demonstrated by uptake studies in transfected cell lines, and likely serves as a critical component of the observed liver-targeted tissue distribution profile. Preclinical anti-diabetic oGTT efficacy is demonstrated with nicotinic acid-based, liver-targeting SCD inhibitor 10, and studies with a close-structural analog devoid of SCD1 activity, suggest this efficacy is a result of on-target activity.

MeSH terms

  • Administration, Oral
  • Animals
  • Cell Line
  • Drug Evaluation, Preclinical
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / chemistry*
  • Hypoglycemic Agents / pharmacokinetics
  • Hypoglycemic Agents / pharmacology*
  • Liver / drug effects
  • Liver / enzymology
  • Mice
  • Mice, Inbred C57BL
  • Nicotinic Acids / chemical synthesis
  • Nicotinic Acids / chemistry*
  • Nicotinic Acids / pharmacokinetics
  • Nicotinic Acids / pharmacology
  • Rats
  • Stearoyl-CoA Desaturase / antagonists & inhibitors*
  • Stearoyl-CoA Desaturase / metabolism
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • Enzyme Inhibitors
  • Hypoglycemic Agents
  • Nicotinic Acids
  • Stearoyl-CoA Desaturase