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5'-halogenated analogs of oxymorphindole.

Matthew D Metcalf1, Andrew Coop

  • 1Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, MD 21201, USA.

Bioorganic & Medicinal Chemistry Letters
|September 11, 2007
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Indolomorphinans with a 6,7-fused indole group were thought selective for delta opioid receptors. However, 5-halogenated oxymorphindole analogs show limited delta opioid receptor selectivity over mu opioid receptors.

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Area of Science:

  • Medicinal Chemistry
  • Neuroscience
  • Pharmacology

Background:

  • Opioid ligands are crucial for pain management.
  • Indolomorphinans were previously associated with delta opioid receptor selectivity.
  • The 6,7-fused indole moiety was hypothesized as the key structural feature for this selectivity.

Purpose of the Study:

  • To investigate the role of the 6,7-fused indole group in opioid receptor selectivity.
  • To synthesize and evaluate 5'-halogenated analogs of oxymorphindole.
  • To determine the mu-opioid and delta-opioid receptor binding affinities of these novel analogs.

Main Methods:

  • Synthesis of 5'-halogenated oxymorphindole analogs.
  • Radioligand binding assays to determine receptor affinity.
  • Pharmacological characterization of novel opioid ligands.

Main Results:

  • The 5'-halogenated oxymorphindole analogs demonstrated significantly reduced selectivity for delta opioid receptors.
  • These analogs exhibited comparable affinity for both mu and delta opioid receptors.
  • The presence of the 6,7-fused indole group is not the sole determinant of delta opioid selectivity.

Conclusions:

  • The hypothesis that the 6,7-fused indole group confers delta opioid selectivity is challenged.
  • 5'-Halogenation of oxymorphindole leads to non-selective mu/delta opioid ligands.
  • Further structural modifications are needed to achieve delta opioid receptor-specific ligands.