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Kinetics and Mechanism of Fentanyl Dissociation from the μ-Opioid Receptor

Paween Mahinthichaichan, Quynh N. Vo, Christopher R. Ellis, Jana Shen

2021JACS Au42 citationsDOIOpen Access PDF

Abstract

, the calculated τ are 2.6 and 0.9 s, respectively. Analysis suggests that formation of the piperidine-Hid297 hydrogen bond strengthens the hydrophobic contacts with the transmembrane helix (TM) 6, allowing fentanyl to explore a deep pocket. Considering the experimental τ of ∼4 min for fentanyl and the role of TM6 in mOR activation, the deep insertion mechanism may be biologically relevant. The work paves the way for large-scale computational predictions of opioid dissociation rates to inform evaluation of strategies for opioid overdose reversal. The profound role of the histidine protonation state found here may shift the paradigm in computational studies of ligand-receptor kinetics.

Topics & Concepts

FentanylChemistryDissociation (chemistry)ProtonationOpioidMetadynamicsOpioid receptorStereochemistryMolecular dynamicsPharmacologyReceptorComputational chemistryMedicineBiochemistryIonPhysical chemistryOrganic chemistryNeuropeptides and Animal PhysiologyReceptor Mechanisms and SignalingPharmacological Receptor Mechanisms and Effects
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