Resonance Energy Transfer Relates the Gas-Phase Structure and Pharmacological Activity of Opioid Peptides

Angewandte Chemie
Vladimir Kopysov, Oleg V Boyarkin

Abstract

Enkephalins are efficient pain-relief drugs that bind to transmembrane opioid receptors. One key structural parameter that governs the pharmacological activity of these opioid peptides and is typically determined from condensed-phase structures is the distance between the aromatic rings of their Tyr and Phe residues. We use resonance energy transfer, detected by a combination of cold ion spectroscopy and mass spectrometry, to estimate the Tyr-Phe spacing for enkephalins in the gas phase. In contrast to the condensed-phase structures, these distances appear to differ substantially in enkephalins with different pharmacological efficiencies, suggesting that gas-phase structures might be a better pharmacophoric metric for ligand peptides.

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Citations

Mar 8, 2016·The Journal of Physical Chemistry Letters·Vladimir KopysovOleg V Boyarkin
Dec 20, 2016·Analytical Chemistry·Vladimir KopysovOleg V Boyarkin
Jan 21, 2017·Physical Chemistry Chemical Physics : PCCP·A Y Pereverzev, O V Boyarkin
Mar 25, 2017·Physical Chemistry Chemical Physics : PCCP·Alexander KuleszaPhilippe Dugourd
Mar 5, 2016·Journal of the American Society for Mass Spectrometry·Moritz SchennachKathrin Breuker
Nov 1, 2017·Angewandte Chemie·Jakub UjmaPerdita E Barran
Mar 30, 2019·Angewandte Chemie·Erik SaparbaevOleg V Boyarkin
Oct 4, 2019·Physical Chemistry Chemical Physics : PCCP·Aleksandr Y PereverzevOleg V Boyarkin
Nov 2, 2017·The Journal of Physical Chemistry. a·Tapta Kanchan RoyR Benny Gerber
Jun 1, 2018·The Journal of Physical Chemistry Letters·Valeriu ScutelnicThomas R Rizzo
Aug 20, 2019·Chemical Reviews·Satchin SoorkiaGilles Grégoire

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