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Fentanyl binds to the mu-opioid receptor via the lipid membrane and transmembrane helices

Sutcliffe, K. J.; Corey, R. A.; Charlton, S. J.; Sessions, R. B.; Henderson, G.; Kelly, E.

2021-02-05 pharmacology and toxicology
10.1101/2021.02.04.429703 bioRxiv
Show abstract

Overdose deaths from synthetic opioids, such as fentanyl, have reached epidemic proportions in the USA and are increasing worldwide. Fentanyl is a potent opioid agonist, that is less well reversed by naloxone than morphine. Due to fentanyls high lipophilicity and elongated structure we hypothesised that its unusual pharmacology may be explained by a novel binding mode to the -opioid receptor (MOPr). By employing coarse-grained molecular dynamics simulations and free energy calculations, we determined the routes by which fentanyl and morphine access the orthosteric pocket of MOPr. Morphine accesses MOPr via the aqueous pathway; first binding to an extracellular vestibule, then diffusing into the orthosteric pocket. In contrast, fentanyl takes a novel route; first partitioning into the membrane, before accessing the orthosteric site by diffusing through a ligand-induced gap between the transmembrane helices. This novel lipophilic route may explain the high potency and lower susceptibility of fentanyl to reversal by naloxone.

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