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Structural Properties
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Increasing Thyromimetic Potency through Halogen Substitution.

Jordan Devereaux1, Skylar J Ferrara1, Tania Banerji1

  • 1Department of Physiology & Pharmacology, Program in Chemical Biology, Oregon Health & Sciences University, 3181 SW Sam Jackson Park Road, Portland, OR, 97239, USA.

Chemmedchem
|October 13, 2016
PubMed
Summary

New halogenated thyromimetics show enhanced potency and central nervous system (CNS) penetration compared to sobetirome. These compounds may offer new therapeutic options for CNS disorders by targeting thyroid hormone receptor beta (TRβ).

Keywords:
braincentral nervous systemthyroid hormonesthyromimetics

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Area of Science:

  • Medicinal Chemistry
  • Endocrinology
  • Neuropharmacology

Background:

  • Sobetirome is a well-studied thyroid hormone receptor beta (TRβ)-selective thyromimetic.
  • Thyroid hormones play crucial roles in central nervous system (CNS) development and function.
  • TRβ-selective thyromimetics are investigated for treating various disorders.

Purpose of the Study:

  • To synthesize and evaluate novel halogenated analogues of sobetirome.
  • To assess the in vitro and in vivo potency and selectivity of these new compounds.
  • To determine the potential of these analogues for treating CNS disorders.

Main Methods:

  • Structural modification of sobetirome by replacing methyl groups with chlorine or bromine.
  • In vitro assessment of TRβ-mediated transactivation using cell-based reporter assays.
  • In vivo evaluation of CNS penetration and activation of endogenous TR-regulated genes in the brain.

Main Results:

  • Halogenated analogues exhibited significantly increased potency compared to sobetirome.
  • These compounds demonstrated EC50 values comparable to T3 in TRβ-mediated transactivation.
  • The analogues achieved similar CNS levels as sobetirome and activated brain TR-regulated genes with higher potency.

Conclusions:

  • Structural halogenation enhances the potency of sobetirome analogues.
  • The enhanced affinity may be attributed to halogen bonding interactions within the TRβ receptor.
  • These potent TRβ-selective thyromimetics are promising candidates for CNS disorder therapies.