Dual Sigma-1 receptor antagonists and hydrogen sulfide-releasing compounds for pain treatment: Design, synthesis, and pharmacological evaluation

European Journal of Medicinal Chemistry
2022.0

Abstract

The development of σ<sub>1</sub> receptor antagonists hybridized with a H<sub>2</sub>S-donor is here reported. We aimed to obtain improved analgesic effects when compared to σ<sub>1</sub> receptor antagonists or H<sub>2</sub>S-donors alone. In an in vivo model of sensory hypersensitivity, thioamide 1a induced analgesia which was synergistically enhanced when associated with the σ<sub>1</sub> receptor antagonist BD-1063. The selective σ<sub>1</sub> receptor agonist PRE-084 completely reversed this effect. Four thioamide H<sub>2</sub>S-σ<sub>1</sub> receptor hybrids (5a-8a) and their amide derivatives (5b-8b) were synthesized. Compound 7a (AD164) robustly released H<sub>2</sub>S and showed selectivity for σ<sub>1</sub> receptor over σ<sub>2</sub> and opioid receptors. This compound induced marked analgesia that was reversed by PRE-084. The amide analogue 7b (AD163) showed only minimal analgesia. Further studies showed that 7a exhibited negligible acute toxicity, together with a favorable pharmacokinetic profile. To the best of our knowledge, compound 7a is the first dual-acting ligand with simultaneous H<sub>2</sub>S-release and σ<sub>1</sub> antagonistic activities.

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