Benzylaminofentanyl derivates: Discovery of bifunctional μ opioid and σ1 receptor ligands as novel analgesics with reduced adverse effects

European Journal of Medicinal Chemistry
2022.0

Abstract

To develop safer and potent analgesics, we designed, synthesized, and evaluated a new series of benzylaminofentanyl derivates as bifunctional μ opioid receptor (MOR) and σ<sub>1</sub> receptor (σ<sub>1</sub>R) ligands. Compound 68 (Tao-191) showed desirable MOR agonism (K<sub>i</sub> = 6.5 nΜ; EC<sub>50</sub> = 48.5 nΜ, E<sub>max</sub> = 66.3%) and σ<sub>1</sub>R antagonism (K<sub>i</sub> = 35.7 nM) in vitro, and exerted powerful analgesic effects in the abdominal constriction test (ED<sub>50</sub> = 0.32 mg/kg, in mice), formalin-induced pain test (phase II, ED<sub>50</sub> = 2.26 mg/kg, in rats), and paclitaxel-induced neuropathic pain model (ED<sub>50</sub> = 0.30 mg/kg, in mice). The contributions of MOR and σ<sub>1</sub>R to its antinociceptive effect were verified by combined administration with the MOR antagonist naloxone and the σ<sub>1</sub>R agonist PRE-084, respectively. At equianalgesic doses, compound 68 induced fewer MOR-related side effects-including physical and psychological dependence, respiratory depression, constipation, and acute hyperlocomotion-than fentanyl. The results provide a rationale for further exploration of the action and safety of dual MOR/σ<sub>1</sub>R ligands as a promising avenue for the development of potent and safe analgesics.

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