Novel (2E,4E,6Z)-7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic acid retinoid X receptor modulators are active in models of type 2 diabetes

J Med Chem. 2003 Jun 19;46(13):2683-96. doi: 10.1021/jm020340q.

Abstract

Previous data have shown that RXR-selective agonists (e.g., 3 and 4) are insulin sensitizers in rodent models of non-insulin-dependent diabetes mellitus (NIDDM). Unfortunately, they also produce dramatic increases in triglycerides and profound suppression of the thyroid hormone axis. Here we describe the design and synthesis of new RXR modulators that retain the insulin-sensitizing activity of RXR agonists but produce substantially reduced side effects. These molecules bind selectively and with high affinity to RXR and, unlike RXR agonists, do not activate RXR homodimers. To further evaluate the antidiabetic activity of these RXR modulators, we have designed a concise and systematic structure-activity relationship around the 2E,4E,6Z-7-aryl-3-methylocta-2,4,6-trienoic acid scaffold. Selected compounds have been evaluated using insulin-resistant rodents (db/db mice) to characterize effects on glucose homeostasis. Our studies demonstrate the effectiveness of RXR modulators in lowering plasma glucose in the db/db mouse model.

MeSH terms

  • Animals
  • Blood Glucose / analysis
  • Caprylates / chemical synthesis*
  • Caprylates / chemistry
  • Caprylates / pharmacology
  • Diabetes Mellitus, Type 2 / blood*
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology
  • Insulin Resistance
  • Male
  • Mice
  • Radioligand Assay
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Retinoic Acid / drug effects*
  • Receptors, Retinoic Acid / metabolism
  • Retinoid X Receptors
  • Structure-Activity Relationship
  • Transcription Factors / drug effects*
  • Transcription Factors / metabolism

Substances

  • Blood Glucose
  • Caprylates
  • Hypoglycemic Agents
  • Receptors, Retinoic Acid
  • Retinoid X Receptors
  • Transcription Factors