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Kappa-opioid receptor-selective dicarboxylic ester-derived salvinorin A ligands.

ABSTRACT: Salvinorin A, the active ingredient of the hallucinogenic plant Salvia divinorum is the most potent known naturally occurring hallucinogen and is a selective ?-opioid receptor agonist. To better understand the ligand-receptor interactions, a series of dicarboxylic ester-type of salvinorin A derivatives were synthesized and evaluated for their binding affinity at ?-, ?- and ?-opioid receptors. Most of the analogues show high affinity to the ?-opioid receptor. Methyl malonyl derivative 4 shows the highest binding affinity (Ki=2nM), analogues 5, 7, and 14 exhibit significant affinity for the ?-receptor (Ki=21, 36 and 39nM).

SUBMITTER: Polepally PR 

PROVIDER: S-EPMC3651692 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Kappa-opioid receptor-selective dicarboxylic ester-derived salvinorin A ligands.

Polepally Prabhakar R PR   White Kate K   Vardy Eyal E   Roth Bryan L BL   Ferreira Daneel D   Zjawiony Jordan K JK  

Bioorganic & medicinal chemistry letters 20130404 10

Salvinorin A, the active ingredient of the hallucinogenic plant Salvia divinorum is the most potent known naturally occurring hallucinogen and is a selective κ-opioid receptor agonist. To better understand the ligand-receptor interactions, a series of dicarboxylic ester-type of salvinorin A derivatives were synthesized and evaluated for their binding affinity at κ-, δ- and μ-opioid receptors. Most of the analogues show high affinity to the κ-opioid receptor. Methyl malonyl derivative 4 shows the  ...[more]

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