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Genetically-encoded Molecular Probes to Study G Protein-coupled Receptors

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Published on: September 13, 2013

3'-functionalized adamantyl cannabinoid receptor probes.

Go Ogawa¹, Marcus A Tius¹, Han Zhou²

¹†Department of Chemistry, University of Hawaii at Manoa, 2545 The Mall, Honolulu, Hawaii 96822, United States.

Journal of Medicinal Chemistry

|March 12, 2015

Summary

Researchers explored how adamantyl groups affect cannabinoid receptor binding. New adamantyl-substituted cannabinoid analogues show improved affinity and selectivity for CB1/CB2 receptors, leading to effective covalent probes.

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Area of Science:

Medicinal Chemistry
Pharmacology
Neuroscience

Background:

The aliphatic side chain is crucial for the potency of tricyclic classical cannabinoids.
Previous studies demonstrated successful substitution of this chain with adamantyl or polycyclic groups.

Purpose of the Study:

To investigate the pharmacophoric features of conformationally fixed adamantyl groups.
To synthesize novel cannabinoid analogues with adamantyl substituents at the C3 position.

Main Methods:

Synthesis of adamantyl-substituted cannabinoid analogues.
Incorporation of electrophilic isothiocyanate and photoactivatable azido groups for covalent attachment.
Evaluation of ligand affinities and selectivities for CB1 and CB2 receptors.

Main Results:

Substitution at the 3'-adamantyl position enhanced ligand affinities for cannabinoid receptors.
Achieved improved CB1/CB2 selectivity with novel adamantyl-substituted analogues.
Developed two successful covalent probes: AM994 (isothiocyanate) and AM993 (azido).

Conclusions:

Adamantyl substitution offers a strategy to improve cannabinoid ligand properties.
The developed covalent probes (AM994 and AM993) exhibit high affinity for cannabinoid receptors.
This research provides insights into structure-activity relationships for cannabinoid receptor ligands.